Dating After Divorce

Top 10 Rules for Dating in New York City – If you’re completely over it and don’t give a shit anymore.

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After a three-year stint of completely avoiding the dating scene in New York City I dared to venture back into the fray.  I’m probably going to opt out again any day now as it’s just as screwed up as it’s ever been.  Here are my handy tips if you’ve hit the wall and nearly given up hope.

1. If your date actually shows up you are halfway there – It’s next to impossible to get a man to actually agree to a date.  Expect nothing.  When I say nothing I mean exactly that.  Will your date show up?  Maybe!  He might look completely different from the person in his photos.  You might get a cancellation as late as several minutes into your planned encounter.  He might meet you briefly and then drag you into a social situation full of strangers.  Once on a second date I was introduced to an entire dinner party full of friends along with my date’s teenage daughter.  The two of us clicked right away because neither one of us wanted to be there.  Her first words to me were about how her mother had been arrested in an European airport for throwing a temper tantrum.  Needless to say that I didn’t end up dating her father.

Pro-tip – If your date doesn’t show up order a dirty martini and just start talking to random strangers.  You’ll probably end up with a new gay male best friend.  That’s what’s happens to me anyway.

2. Cyberstalk the shit out of the person – Not only do I advise doing this, I think you’d be reckless to not google them.  I’ve found articles and images my dates didn’t know existed.  I’ve made the mistake of telling complete strangers what I’ve found on them.  Men tend to misread this one.  I’m just making sure they’re not married, a serial killer or using an alias.

Pro-tip – Do NOT scroll through the comments section.  The comments section on any social media account will reveal too much.  I’ve figured out who is an ex-girlfriend, who might want to be the next girlfriend and even exact dates of breakups.  If you want to leave some mystery feel free to scroll through the images, just avoid the commentary.  If a person wants privacy they wouldn’t be putting these images online.  I don’t know how many people I’ve had to point this out to before.  If you put it on Instagram, Twitter, Facebook or any other social media app we can all see it.  If you want privacy then change the privacy settings for those accounts.

3. Avoid initiating all correspondence after a date – New Yorkers like their partners silent and hassle free.  If you contact them at all for any purpose whatsoever you risk being branded a “Crazy clingy psycho” even if you only text them a handful of times.  Don’t call them on the actual phone, I you do that you’ll freak them out so much they’ll probably notify the police.  If you are unconventional like myself and contact someone via email or on social media they might move to another state to avoid your stalker ways.  I’m strange in that I tend to interact with most of my friends on social media.  I’ve found when I do this to men I barely know or have never met they completely misread it.

Pro-tip – As soon as you walk away from the date immediately delete his number.  I wish I was actually capable of this but I’d still strongly suggest you try it.

4. Become a semi-professional pornographer – Like dick pics?  Well it’s your lucky day, you’ll get plenty!  Worried about having nude or semi-nude photos of yourself floating around the internet for all of eternity?  What are you some kind of uptight prude?  Buy some lighting, get a good camera and Photoshop out any tattoos that might reveal your identity.  Fall in love with close-ups of your genitalia because people you’ve hung out with for less than two hours will come asking for them.  You’ll sometimes get these requests before your first date.

Pro-tip – You never know where those photos are going to end up.  Send them a photo of a cat or Dick Cheney.  Fuck with their head.  Give them nothing.

5. Learn to love spontaneity – Like planning more than a day in advance?  Have an unusual schedule that can be difficult to plan around?  Well then you’re never dating anyone.  If you won’t jump up at a moment’s notice and meet some guy you barely know in a dive bar in the Lower East Side,  you’re never getting laid again.  Get used to meeting up with men when they’re already half drunk.  You might be the second or third woman they’ve texted that night.  Once I showed up to a bar only to meet another woman who was also beckoned.  He’d made a mistake and didn’t realize we might both show up.  He didn’t get laid but I’m still friends with the woman to this day.

Pro tip – Find someone with the same batshit crazy schedule as yourself.  It might seem impossible which why I also suggest learning to love YouTube clips from “Mad Men” watching images of Jon Hamm might just be enough, it usually is for me anyway.

6. You’ll be judged harshly for all of your life choices up until this point – Did you go to state college?  Did you major in the arts?  Do you live with five roommates?  Are you divorced?  Have you ever lived with anyone?  How many stupid jobs have you had?  Bernie Bro or HRC?  If you call yourself a moderate you basically are admitting you’re a Neo Nazi.  You will be judged, cataloged and written off for the slightest offense or sign of eccentricity.

Pro-tip – Judge back.  Go deep.  If he gives you grief for having three cats shame him for not opening his life and apartment up to one of the millions of unwanted animals languishing in shelters.  How dare he live his life WITHOUT a cat.  So what if he’s allergic there are LIVES TO BE SAVED HERE!

7. Expect lazy dates – Would you feel comfortable going over to a stranger’s apartment for a glass of wine for a first date?  Why not?  Maybe you don’t like being dismembered, date raped or being trapped in an apartment with a drunken fool.  I’ve been asked out for that exact scenario more than once.  I know I’m such an uptight bitch for insisting on a public location full of potential witnesses but I’m old fashioned that way.

Pro-tip – Always insist on a public place for a first date and when in doubt make up an annoying texting friend so you can leave whenever you want.

8. Find the right slut balance – The Madonna/Whore complex runs deep in the urban male.  Men will expect and hope that you will have sex with them minutes after you meet them.  If you decide to take the plunge too early you’ll be branded a worthless slut and discarded accordingly.  If you try to hold out for a second or third date you might be considered a sexless puritanical old maid.  If you’ve survived date one without putting out then you enter the dangerous territory of the space between date one and two.  Will you have to whip out your own personal Penthouse level quality snapshots?  Or will you be expected to sext, flirt or engage in XXX Instant Messaging.  Have a web cam?  All the better just don’t go full porn star or you’re not likely to hear from him again.  The only exception of course is if you’re in the polyamorous group.  Then there are no rules.  The slut balance is your balance.  

Pro-tip – I’ve got nothing.  Use condoms.  You’re still going to get at least three strains of HPV with condoms anyway but you’ll hopefully avoid The Clap or maybe some new antibiotic resistant strain of Gonorrhea doctors won’t be able to treat yet.

9. Dates will ask for full disclosure – Where do you live?  That’s probably priority #1 because no one wants to put any effort forth.  If they live in Bushwick and you live in Bay Ridge the chances of a second date are slim to none.  If you meet someone who lives in another borough it had better be a 15-20 minute commute or it’s never going to happen.  You can live more than 30 minutes away but it had better be on the same train line and not require a transfer.  How much do you make?  Who did you vote for in 1992?  Were you old enough to vote in 1992?  What do you do for a living?  How many kids do you want to have?  Do you have kids?  What is your drug history?  What drugs do you do on a regular basis?  Don’t be surprised if your date asks you about specific sexual preferences or peccadilloes.  

Pro-tip – Tell them everything.  Declare things they never even asked about.  Reveal your last boyfriend’s dick size and shape.  Why not?  They’ll probably find it out while cyberstalking you anyway.

10. Practice Self-Care – Find a beautiful spot in nature such as a park, beach or flower garden.  Pick up a mason jar, hold it closely in your hands.  As you hold meditate and manifest all the things you’d love to find in a good partner.  Visualize everything down to specific details.  Feel their touch of their hands, hear the sound of their voice, and smell their scent.  Then open the jar, put it close to your mouth and let out a long and passionate gutteral scream.  Seal the jar and bury it.  That’s the last time you’ll be able to express any real emotion.  Emotion is for suckers.  If you want to successfully date in New York City you need ice water in your veins.

Pro-tip – Expect to have breakdowns.  If you’re going to try to date in this town you’re going to have breakdowns.  When in doubt get a cat.  I have three.  I still have breakdowns.

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NYC Dating – Men of NYC – I’m just not that into you.

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One of the main reasons I hate online dating is that it throws off the traditional straight male and female dynamic.  I don’t care what study or survey claims to the contrary – straight men HATE it when women are aggressive.  There are exceptions to this rule of course but they are few and far between.

As a woman with a somewhat dominant personality I know this all too well.  I speak plainly.  I say exactly what I’m thinking.  There is very little subtext in anything I do or utter.  I don’t even know how to operate in a manipulative way.  The whole idea of saying one thing while meaning something else completely baffles me.  I realize this trait of mine is unusual.  It tends to get me in trouble when it comes to dating.

Most straight men want to pursue a woman.  They want to woo her and win her over as if she is some sort of rare albino gazelle on the grasslands of Africa.  The pursuit feeds their ego, it makes them feel like the woman is some sort of rare gem, and it makes them feel like they’re in control.  Any woman who makes it known too early that she is also actively pursuing a man is seen as less desirable, desperate or pathetic.

Here’s the thing gentlemen of the city that never sleeps.  Despite being 45 years old and being far from perfect I can still get just about any man.  If all I’m looking for is no strings attached sex it’s not a problem.  If I only want to have sex with the man once and never see him again it’s even easier.  I’m not including married men and men in committed relationships when I say that, although I get plenty of offers from men who aren’t exactly single.   I’m not bragging.  I’m not unique or exceptional.  Nearly any woman within a reasonable age range can bed just about any single and available man.   Men pay for the privilege of getting sex.  They spend hours in strip clubs in a sexually charged environment.  Some will waste most of their leisure time watching porn.  Sex for men can be difficult to come by but for most women sex is easy.  It’s almost too easy.  There’s no challenge in it.  There’s no game.  Simply be willing and able and give no signs that you expect anything but sex and most women can bed whomever they please.

This is where online dating comes in.  The dynamic of men pursuing women gets completely thrown off because half the apps make it next to impossible for men to start the ball rolling.  I understand why this is as most women get inundated with sexually explicit requests when there are no safeguards.  What happens instead is now the woman have to make the first move.  It might seem great in theory but it tends to make men think we are far more interested than we actually are.  I honestly have incredibly low expectations for any man I meet online.  I don’t expect much because I’ve been on so many bad dates.  The whole thing is a crapshoot.  Most times it’s just two strangers awkwardly trying to figure out a way to bolt and go home.  It’s no one’s fault, it’s just how dating random people tends to work out.

I never want to get married again.  I don’t want to move in with someone.  I’ve given up on having children. So rest assured I’m not planning our wedding.  I’m certainly not wondering how I’ll re-arrange my life when we move in together and I’m not naming our future children.  What I do want is to physically go out with someone and see them on a semi-regular basis.  My bar is low.   I don’t think any man is perfection personified.  I’ve been married and divorced.  There’s no way I would ever fall for anyone instantly.   If you are a decent human being, treat me well and we have even scant chemistry I’ll probably want to go out with you again.  That’s it.  That’s as deep as this ocean gets when I barely know someone.

Since I’ve been single I’ve had more requests for virtual sex than the real thing.  I’ve been asked to drop everything on a moment’s notice to hookup with some guy in the middle of the night.   I get solicitations for nude photos before I’ve even been intimate with a man.  I guess that’s just expected now since we all have mirrors and we all have phones.  

I AM BEYOND SICK OF THIS NONSENSE.

Your offers of no strings attached casual sex are about as common and inviting as the blackened pieces of chewing gum pounded into any subway platform.  I love sex but I also like knowing the person a little before I have sex with them.  I want to go see movies, have a meal or maybe go for a hike.  I want to share my day with them and ask them how their day went.  That’s it.  I’m not asking for much here.

When I’ve tried to just park it and let men take the lead on those dating sites basically nothing happens.  No one asks me out.  I get no email.  I just wonder why this got so difficult.  I don’t know what happened to dating.  I don’t understand how I’m supposed to interact in a world full of confusing text messages, sexting and booty calls.

I just want and crave actual human interaction more than I could possibly express here.  So sorry men of New York City I’m not really into you.  I don’t care how much money you make or where you work.  I don’t give a rat’s ass if you have some sort of award or if you’re famous.  The fact that you are published or work for a hedge fund does not impress me.  I’d rather watch clips of Adam Driver or Jon Hamm and let my imagination wander than put up with this dehumanizing endeavor.   Why is this so hard?  I’ve given up trying to figure it out.  I’m just screaming into the void at this point.  Dating as we know it is dead and for some reason I just keep going to funerals expecting the corpse to jump up and start dancing.

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Dating in NYC – The Dreaded Ghost

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People ask me all the time why I’ve decided to label myself as feral and completely leave the dating pool.  I admit my self-classification as “feral” is tongue-in-cheek.  It’s just my way of fully embracing my single identity.  A number of things have made me disillusioned about dating in the Big Apple.  The worst thing I’ve encountered more than once though is the dreaded ghost.  It’s not a wandering spirit or aberration who hasn’t made peace with the afterlife.  A ghost in terms of dating is a partner who’s decided to simply walk away with no contact or explanation after an intimate encounter.

The worst example ghosting happened to me years ago.  The man was someone I knew well, or at least I thought I did.  To protect his identity I won’t reveal anything about him – his age, occupation or any physical characteristics.  I’ll simply call him Kevin, although that’s not his real name.

Kevin worked with me in a situations where we were often stuck together for 12-14 hours at a stretch.  We weren’t close friends but we could talk easily and had decent chemistry.   He was always a bit flirtatious but things accelerated for some reason after we knew each other about three years.  I worked with Kevin in a freelance situation so I didn’t see him on a regular basis.  I was definitely attracted to him but I was extremely unsure about the situation since we sometimes worked together.  He was also  bit younger than me, but most single men I encounter are at least 8-10 years my junior if not more.  He made it clear that he just wanted to hookup.  I wasn’t sure about it but I hadn’t had sex in forever and the only offers I was getting at the time were for casual sex from total strangers.  At least I knew Kevin.  I remained hesitant and Kevin went so far as to call me on the phone and talk me into it at length.   I was impressed that he called me as it seemed no man in New York City knew that phones could actually be used to make phone calls.  Most men sent texts usually filled with smut and the occasional dick pic.  A phone call seemed old school and classy.

The plan was made.  He picked me up from a job I had we went back to his place.  He treated me politely and friendly as he always had in the past.  The sex was intense and over the top.  The build up of three years had sort of worked its magic.  As soon as things were done, he turned away from me as if I was toxic waste.  I was a bit shocked as I wasn’t expecting cuddling afterward but his body language was extreme.  Not one molecule of his body was touching mine.  It was as if I wasn’t there.  The first few moments were incredibly awkward.  I decided to break the tension by mentioning something personal about him.  I saw a sports jersey that was hanging in a prominent position in his bedroom and asked him.

“What’s that from?  Are you on a team or something?”

He responded.

Why are you asking that?  I’m not going to tell you that.

It was as if a switch had gone off in his brain and he was punishing me for having had sex with him.  I lied there wondering how I messed up this situation so badly.   I never did this.  I hated hookups. I had known this man for years.  When he was convincing me to do this with him he kept me on the phone for over an hour.  Now he was treating me as if I had crawled into his window uninvited.  A feeling of dread passed over my body.   I felt like I wasn’t even there anymore and that I was somehow floating above the bed.  What the hell just happened?

Some pleasantries were exchanged.  He apologized for not being able to give me a ride home.  I insisted on taking the subway anyway.   I walked myself to the subway stunned and sickened.  The whole experience was 100% consensual but he made me feel like I was a used Kleenex he tossed after masturbating.

I waited a few days and sent him a text about a gig I knew he had coming up.  I wished him well.  There were no heart emojis or anything romantic.  He was short and brusque back.  I thought maybe I was reading too much into it.  Maybe I was projecting things on him that weren’t there.  I waited a few days and sent a couple more texts only to get blanked over the next week or so.  I kind of snapped and started sending him pleading messages.  I just wanted a response, any response.   I wasn’t professing my love to him, I wasn’t expecting an instant boyfriend.  I had no expectation that we would start dating.  I was just reaching out.  I’d known him for three years.  I thought he was my friend.  The whole thing felt like some epic Madonna/Whore test that I had failed miserably.  I’m not sure if I was supposed to continually spurn his advances or go full Jezebel and ask him for a three-way with a woman I picked up on OKCupid.

He never responded again.  Since my divorce I haven’t exactly had the greatest track record dating but my experience with Kevin was by far the worst.  My head was filled with the same thoughts bouncing back and forth through my skull for days.

How could he do this to me?  He knows me.   I’m not some stranger off the street.  What the hell is going on?  Why is he treating me like garbage?  What’s wrong with me?

It wasn’t that Kevin was some great prize or that I wanted a relationship with him.  I was just shocked that he treated me so horribly.   Without hesitation that experience has been the worst consensual sexual experience of my life.  It wasn’t abuse just inconsiderate and callous.  I played the whole incident over and over again in my mind trying to figure out what I had done wrong to make him treat me this way.  I decided that it didn’t matter.

Of course I did run into him again a few months later in work-related scenario.  As soon as I saw him he looked right at me.  I diverted his gaze.  I decided in the moment to act  like I had no idea who he was.  If he was going to treat me with such disregard I’d do the same.  His response was not surprising as he kept staring at me from across the room.  I’m not sure how he was expecting me to react.  What was I supposed to do? Run up to him and embrace him?  Ask him what he was up to the past couple of months?  I just wanted him to disappear.  Finally near the end of the job I was being ushered by my supervisor right next to where he was standing.  I could feel his eyes burning into mine but I refused to make contact.  When things got to the point of absurdity I turned to him and said simply “Hey Kevin” and kept walking.  I didn’t even make eye contact.  If he had tried to talk to me I would have just nodded and walked away.

The hardest part of it was not blaming myself.  I dissected and analyzed everything I said and did in the time I spent with Kevin trying to figure out what caused him to be that way.  Ironically the whole experience would have been much easier to get over if Kevin was a total stranger.  In his mind I was just garbage and if I wanted to be treated better by men I would have to go back to my old standard.  A guy would have to ask me out on a proper date and put some effort forth.  If they wanted a no-strings attached sexual situation then they could ask someone else.  I don’t judge others who live that lifestyle it’s just a bad fit for me.

Things haven’t gotten much better.  I’ve been ghosted since my fling with Kevin.  I wish I could say there was some sort of magical set of clues that would indicate when a seemingly grounded man will emotional disappear but I’ve got none.  I’ve sadly learned to expect it.

I never saw Kevin again and I’m glad I haven’t.  If I did see him he’d simply be someone I have no recollection of meeting much less having sex with.  Feral life suits me better anyway – no attachments, no commitments and no expectations.  I’d rather have nothing than the dreaded ghost.

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Dating After Divorce: On Turning Feral…

A couple of years ago while watching a documentary I discovered a house cat can revert to its natural state under the right circumstances. I imagined my obese ginger male going from his prescription canned cat food to hunting and feasting on rodents and birds. His once silky coat now matted with dirt and leaves. His fat haunches transformed into lean muscle.  Instead of dramatically crying for his supper twice a day, he’d hide in alleys and beneath parked cars avoiding contact with humans while ruling the night. As I stroked Otto’s fur I decided I’d was no longer single, I’d turned feral instead.

When I  went through a difficult divorce nine years ago I suspected my dating life would be difficult.  I had no idea it would become a soul-crushing, near impossible endeavor.  Right out of the gate, I had two fairly tragic rebound relationships that imploded almost as soon as they’d started. Online dating felt more like an exercise in attrition and increasingly lowered expectations.  I’d get the obligatory emails from men involved with BDSM – twice as many submissives than dominants. Couples would email me hoping I want to join in some three-way play. My inbox would overflow with email from men in other countries and far away states. Traveling business men would contact me late at night, expecting me to drop everything to run to their hotel room and be their unpaid prostitute.  Dates rarely materialized and if they did they were often two awkward people sitting across from each other with nothing in common but judgmental stares.  Men openly criticized me for my profession, the circumstances around my divorce, and pretty much every lifestyle choice I had made up until the point of meeting them. When I met men offline it seemed like the only interested parties were either married or so young they could easily be mistaken for my son. I’d also met guys who expected me to go home with them five minutes after meeting them. If I showed any hesitation at all I was quickly forgotten for the next random woman who would say yes.

When I showed interest in anyone I was usually treated like a completely crazy person. I realize I’m not every man’s dream woman.  I have a big personality.  I talk a lot.  I’m so nerdy that I can blather for hours about the rise of fascism or the madness of Kaiser Wilhelm II. I won’t know anything about the latest movie that came out but I could tell you more than you’d ever want to know about the life of Nikola Tesla or how mutations take hold in a genome.  I’m opinionated and stubborn.  I will disagree and challenge men often and openly.  For amusement I get onstage and yell at total strangers in darkened basements that are masquerading as makeshift comedy clubs.  I’m a sledgehammer of truth.  Some folks find my qualities charming while others, find them incredibly annoying. My natural nemesis seems to be the classic khaki wearing, boat shoed finance bro alpha male. On multiple occasions I’ve found myself in screaming matches with a half drunk, angry day trader minutes after meeting them.

I’m also not all that interested in finding my dream man.  I have massive trust issues and pretty much assume every man is lying to me from the moment they open their mouth.  Because my ex-husband was a closeted gay man I pretty much assume all men are gay until proven otherwise.  Any nurturing qualities left in me were stamped out by my dysfunctional and broken marriage.  I don’t want to fix a man, pay his rent, make him forget his last girlfriend or guide him through rehab.  If he’s not ready to wear I’ll just toss him back on the pile.  I have zero interest in being an unpaid and untrained psychotherapist. There’s no part of me that longs to hang out with people I can’t stand because they’re friends with my partner.  I don’t want to sit through plates of hot wings and beer when I’d rather have vegetarian Chinese takeout. If he’s wounded and broken, I’ll leave him for someone who can handle wounded and broken.  I’ve got a freight train worth of emotional baggage and a hair-trigger that will cause me to bolt the second I sense danger.  If a man blanks me on a text, I will delete them from my phone.
I’ll leave my apartment with glasses, messy hair, ball caps and dirty jeans.  No fucks are given.  I watch my weight like a hawk because I have to for my industry but I honestly don’t care if someone finds me “pretty.”

I’ve got no online dating profiles. I waste no glances as men walk by. I pose no questions about a man’s dating status.

I live in an apartment the size of an average single car garage. My 450 square foot space is so small that no man would look at it and see an inch for his belongings. There’s no spare drawer or extra closet space. If I was actually trying to date I’d issue parking rules on my front door. – Four hour minimum or mandatory tow.

I look forward to my future as I grow increasingly strange and eccentric.  I’ll become the 60-year-old with blue hair who still wears Doc Martens and has birthday parties for my cats.  The lack of companionship has caused entire sections of my personality to atrophy and die.  I encourage others now to eschew the label of single and embrace the feral mindset.  We are no longer waiting for our Mr. or Mrs. Right, we are hunting proverbial birds and mice in the night and loving every second of it.

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Communication: How to Avoid an Awkward Date from Hell

Last week a debate about what constitutes sexual assault and what doesn’t erupted on social media.  I won’t rehash the horribly written article about Aziz Ansari and I won’t hyperlink to it either.  That site has gotten plenty of traffic in the past week.  I don’t want to debate the language, tone or content of the piece.  Whatever could be said about it has been said about it.  I’ve officially reached Aziz fatigue.

What I do want to continue however is the discussion about the weird grey area that exists between enthusiastic obvious consent, and less than thrilled uneasy consent.  This is a very real problem for both genders, although women have been conditioned to accept it more so than men.  Most of us have been there.  We agree to do something sexually that we’re not sure we want to do.   Again, I’m not referring to the Aziz article or anything in it, I just wanted to explore what many of us talked about in discussions about awkward sexual experiences.  In a perfect universe we should strive for obvious enthusiastic consent, but we’re also not going to get rid of hundreds of years of social conditioning overnight.  We are currently in a strange new world where some of the shame and stigma regarding human sexuality has been lifted, while still living with outdated perceptions of gender norms and what constitutes appropriate behavior.

The most compelling insight on the piece came from a surprising source – the sex positive community.   I have a few friends who are so sex positive they have orgies for fun.  They plan sex parties for a living.  Many of them are in polyamorous or non-monogamous relationships with multiple partners sometimes of both genders.  Some of them have worked as strippers, prostitutes, dominatrixes and even sexual surrogates.  They speak of their sex lives as easily as most of us would talk about our pets or hobbies.  They openly brag about having over 100 sexual partners or more.  The general tone that I got from nearly all of them was.

What we have here is a lack of communication.

For decades it’s been drilled in our heads that we are not supposed to talk about sex.  Human sexuality is rarely something we have frank and open conversations about, at least with new sexual partners.  We are fed a myth our entire lives that amazing sex can be had with total strangers with very little communication.   The exact opposite is true.

Sex is like rocket fuel to humans.  It’s so important to us it’s literally how we create human life, yet at the same time we try to treat it like it’s something we can engage in without a second thought.  Of course we can but we need some ground rules with a new partner if that’s going to happen.  No one would think to jump out of an airplane without first being shown how to use a parachute.  I don’t know why we can think we can magically enter into highly emotionally charged situations without figuring out appropriate boundaries first.

This list is about some of the strategies a person can use to avoid awkward, clumsy and uncomfortable consensual sexual encounters.

Everything on this list with a couple of exceptions is meant for BOTH GENDERS.  Although I wrote this with straight couples in mind, some of the same principles could be applied any sexual orientation or gender identification.

*This list is only in regards to consensual sexual encounters.  No amount of communication will deter a sexual predator.  In those cases the only thing a person can do is  physically fight back, escape a situation or scream for help if that’s an option.  I want to make this distinction now as I don’t want anyone to think a person can simply talk their way out of a sexual assault.  I speak about this as a survivor of sexual assault myself.  Sexual assault is a criminal act where one half of the situation is given no agency, no control, no voice and no choice.  

Tips for avoiding awkward sexual experiences.

Ask for what you want. 

There is nothing wrong with simply asking for what you want.  Both partners should be direct and open about boundaries and comfort levels.

The phrase “Do you want to have sex?” can be very sexy.  It’s also incredibly unambiguous.   The phrase “Can I kiss you?” can also be smolderingly hot if said in the right situation.  It’s also perfectly acceptable to say what you don’t want.  The best way to do this is to use clear language that cannot be misunderstood.  Words like “No” “Stop” or “I don’t want to do this” are hard to misinterpret.  Again this goes both for men and women.  Men also find themselves in situations where they are not comfortable.  Neither partner can assume the other one knows what they want without direct communication.

You are NEVER obligated to do anything you don’t want to do. 

It doesn’t matter how much someone spent on a date.  It doesn’t matter what you’ve already done on a date.  Making out doesn’t mean you consent to oral sex.  Having oral sex doesn’t mean your consent to anal sex.  Having anal sex doesn’t mean you consent to new partners being added to the mix.  If you don’t want to reciprocate or you’re not feeling it you can say no.  You can stop at any time in the date.  It might be awkward or strange to end the date abruptly, but the momentary awkwardness will be easier in the long-term than going through with something you’re not sure you want to do.

You don’t have to be polite if you don’t want to do something. 

This is the only guideline on this list that is directed at women more than men.  As women we are programmed almost from birth to be nice, sweet and accommodating.  When you enter into a sexual act you are kind of putting yourself on the edge of a proverbial cliff.  You don’t really know how your partner might treat you or react.  During a sexual encounter a human being is about as vulnerable as they are ever going to be.  This is not the time to worry about being polite.  If you are freaked out or scared, you can just let it all out.  No need to worry about how you’ll be perceived.  Speak your truth.  Stand up for yourself.  If someone expects you to have unprotected sex and you insist on using protection say NO as loudly and as strongly as possible.  There is NO WAY IN HELL you should put yourself in a potentially medically dangerous situation just to seem nice.

Real life is not a porn movie.  

Porn is probably the worst teaching tool for having great sex.  In most porn scenarios next to no dialog is spoken.  A man somehow just knows that it’s OK to do all sorts of violent and depraved things to a woman he’s just met, he might even include another male partner without even remotely checking in with the woman.  This is of course a fantasy.

Real life is not a fairy tale. 

You might get lucky and have some incredibly romantic near perfect dates that end in beautiful, connected, and full-filling sex with someone you barely know.   It does happen.  It’s quite rare.  Most amazing sex happens with someone you know well and have been having sex for some time.

When in doubt – check it out

If you suspect your partner is not into something stop and ask them.  One of the craziest stories I’d ever heard came from a friend of mine who told me that in the middle of sex a new partner smacked her across the face.  She stopped him immediately and said, “What are you doing?  Why are you doing that?” he claimed his last partner was really into it.  My friend told him she wasn’t.  He stopped.  She never had sex with him again.  Because he immediately stopped the behavior after she requested it, she doesn’t consider this sexual assault.  It’s a great example of a man assuming she would like something his last partner enjoyed.  These assumptions happen all the time with both men and women.  It’s ALWAYS better to check in before you take the risk of entering into behavior that could be seen as predatory, violent or criminal.

If it’s bad early on, it will probably stay bad. 

I hate to say it but you can tell a lot from a kiss.  If a man or woman’s idea of a hot kiss is your idea of a disgusting one, you’ll probably never connect sexually.  It’s fine to simply make up some excuse and get out of the situation before you find yourself in a much more awkward experience later that night.  Everyone goes through this.  If a partner looks great on paper and you like him or her otherwise but her or she repulses you sexually, you’re probably better off not taking things further.

Excessive alcohol use can blur your judgment.

What I just typed is common sense.  What I just typed has also been labeled as sexist, regressive, abusive and part of rape culture.  The problem with the simple statement of “Don’t get drunk” is it’s often only told to women.  Of course women should be able to drink alcohol if they want to and even get drunk.  This exact same advice should also be given to men.  Just as it is far more difficult to drive a car or walk down stairs, it’s also much more precarious to enter into a sexual situation when we are severely intoxicated.  No one is perfect and people will sometimes accidentally drink too much.  The dangers of excess alcohol are just a good thing to remind yourself of if you’re about to go out with a total stranger.  I want to stress this again.  BOTH GENDERS should heed this advice.

Gender specific “rules” that should be thrown out the window

For women

  • Men won’t respect you or ask you out again if you have sex too quickly after meeting them.
  • Don’t go out with him if he asks you out with less than three days notice for a date
  • Don’t go home with a man on a first date.
  • Don’t make out with a man on a first date.
  • Tell him you’ve had three sexual partners in your past. (For most of us that would be a lie)
  • Don’t openly talk about sex or act interested in sex.
  • Never really say what you feel always play the game
  • (Many more rules/assumptions too many to list here – basically that women must remain virginal, pure or at least appear so.  Women must also act coy, not be direct and constantly appear nice)

For men

  • If a woman goes home with you on the first date she wants to have sex
  • If a woman has sex with you on the first date she has less value
  • Any woman can be convinced to have sex with you if you just keep trying
  • If a woman has more than three sexual partners in her past she has less value
  • If a woman makes out with you that means she wants to have sex with you.
  • If a women dresses in a revealing manner she wants to have sex with you.
  • If a woman has joked or flirted with you that means she wants to have sex with you.
  • Never really say what you feel always play the game
  • (Many more rules/assumptions too many to list here but basically that men should pursue, pursue, pursue even when things seem pathetic.  Basically the cliché of a boss chasing his secretary around the desk.)

These are all antiquated ideas about love and sex.  Most of these “rules” leave both genders confused and frustrated.  The best way a man can find out if a woman wants to have sex with him is to ask her directly.  Even though it’s usually wise to avoid sex with perfect strangers, I’ve known several long-term loving relationships that started out just like that.  We have to stop thinking in rigid terms of gender roles and old-fashioned codes of behavior.  We have to smash the ideas of playing hard to get, acting like we don’t really want sex when we actually do, and generally blurring the lines of open communication.  We have to speak up as openly and clearly as possible and empower ourselves to say no when needed.  Again this goes for both men and women.

The last guideline really has nothing to do with awkward sex but is more about the flip side.

You can have great sex with people who are terrible partners

This is probably one of the toughest lessons in life that both men and women learn the hard way.  I think all of my friends have had amazingly hot, passionate sex with people who were absolutely horrible to them.  Sex is great, but if someone is really treating you like garbage outside of the bedroom you’re better off without them.   You can always find another partner who you will click with completely who won’t emotionally abuse or neglect you.

I’ve read a lot of articles regarding this topic that were all saying the same things I’m saying here.  This is also extremely obvious advice, I admit that openly.  I just wanted to get this out in a way that didn’t seem preachy, use words like patriarchy, misogyny, toxic masculinity or any other ism.  Even though this is a widespread problem that is deeply entrenched in our culture we don’t have to think in terms of lofty goals to solve it.  It starts with each and everyone of us.  If we all want to have good sex we just need to start talking to each other about everything and anything.  Don’t feel weird asking questions and never assume you know what’s going on in anyone else’s head.

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Dating in NYC: He says he’s Single. He’s anything but.

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I’ve been single now for about eight years straight since my divorce.  In that time I’ve had a few short-lived relationships but for the most part I’ve flown solo.  I’ve discovered the hard way that the term “single” means a lot of different things to different people.  This city is so large and so densely populated it seems some can’t help but constantly see a never-ending array of choices for potential partners.  I’ve had so many men bold-faced lie to my face regarding this issue that I’m tempted to hand them a survey, and tape the entire exchange so when they say

I never said I was single

I won’t really do that but it’s frustrating that I feel like I have to ask questions like a prosecutor in order to get the truth out of some random dude on a date.

So what does it mean to be “single” in the city that never sleeps?  I’m not including polyamorous or non-monogamous men in this list because they tend to be incredibly upfront and honest about their relationships status.  This is for about the “single” boys who just like to blur the truth.

Single Single: You aren’t having sex with anyone on a regular basis.  You try to date but nothing seems to work out.  You mostly hang out with your friends and maybe watch porn.

Mostly Single: You are casually seeing someone. You’ve hooked up countless times, you socialize together and most of your friends consider you a couple.  Although you’ve both being seeing each other on a regular basis for months neither of you like “labels” and you’re not sure if she’s having sex with other men or not.  You take photos of your friend and post them on social media but never with yourself as a couple.  Even though she’s met your parents and you’ve taken trips together she’s DEFINITELY NOT your girlfriend and as far as you’re concerned you’re 100% single.  You flirt with other women and lead them on, but usually stop short of hooking up with them.

Single on Facebook Single: You’ve been dating someone for months now, you just haven’t bothered to change your relationship status update on Facebook yet.

Friends With Benefits Single: You’ve got a rotation of women that you text on the weekends and late at night for sex.  You like them alright but you’re hoping none of them get too clingy or text you too much. All of these women know they aren’t the only one in your life and you are NOT serious about any of them.  There’s one gal on your list who you tend to text more often and dump all your emotional garbage on them.  For now she puts up with it.  If she starts telling you too much about her life you’re out.  You’re still hoping to find that perfect someone if she exists at all.

Tinder Single: You like to have sex with lots of women, but usually only once. Tinder is your favorite method of hooking up. You sometimes accidentally swipe right on a girl you’ve already banged. Things can get awkward. You’ve also learned it’s better to call women by a pet name since you’ll forget their name seconds after meeting them. They all become honey or babe to you, if you even bother to have a conversation before or after sex.  You’re definitely single but single for life.

We Broke Up I Swear Single: You broke up with your girlfriend months ago but you’re both on a lease and finding a new apartment in tricky in Brooklyn. Neither of you would say you’re dating. You’ve even got a couple of roommates but since this is a three bedroom apartment, that means one of you has to sleep on the couch and there have been plenty of late nights when you’ve ended up hooking up again.  You still fight so it’s a bad situation but it’s only temporary and for the moment you’re looking for love!  Maybe you’ll end up moving in with your next girlfriend.

I’m totally over Her Single: The love of your life just left you. OK she didn’t just leave you it’s been almost two years but you’re TOTALLY over her. Sure you still have every photo you’ve ever taken together on your social media accounts, and yes you still constantly bring her up but you are TOTALLY over her.  You still call her mom from time to time but her mom is a really nice woman.  You’d do the same thing!   Last weekend you helped her move into a new apartment and assembled most of her furniture.  She knows she can call you at any time of the day or night but you are OVER HER.  She’s a great and beautiful person and it just didn’t work out and you wish her nothing but the best.

I’m a Liar I’m not Single: You tell women you’re single because you want to have sex with them.  You’re a married man or you’ve had the same partner for years and have kids with her.  According to the tax code you’re single but by just about every other metric you are very much one half of a couple.

My category – Feral Single – I’ve been single for so long now I don’t know if it’s possible for me to have a relationship anymore.  I LOVE living alone.  I never want to compromise on anything or make any major decisions in my life again that involve another person.  I’ve gone feral.  Like a former house cat who was once fed and cared for I now survive by my wits.  After a long hard day I come home vent on Facebook and talk to my cats.  I’ve become the ultimate loner – self-sufficient, wily, and not likely to be tamed any time soon.

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Dating After Divorce: I like you…but you’re not HER.

The situation goes something like this.  I meet a guy who shows interest in me.  A few have even invested quite a bit of effort and energy to win my favor.  Just when I think I might be letting my guard down enough to actually bond with him, I find out about her.  She might be an ex-girlfriend, an ex-wife, the mother of his child or the one who got away.  She have helped destroy his marriage, or gone out with him on wild benders.  She could have, slept with his best friend, stolen his money, joined a cult, realized she was gay, or stuck around in his life just enough to emotionally manipulate and abuse him.  There are so many ways to become “her.”

I find a problem with “her” in nearly every middle-aged single man I meet.  To be fair I’m sure plenty of women also obsess about a “him” from their past.  It seems as we get older we become a patchwork of our former triumphs and traumas and can’t help but bring them to the next relationship.  Our nostalgia and idealization of former lovers keep us trapped.  Some men are more transparent about this than others.  I’ve had the following happen to me while on first dates with men I barely knew.

  • One admitted his marriage fell apart because he was still in love with his former girlfriend.  He never worked it out with the former girlfriend but his obsession destroyed his marriage.
  • Another said he was still angry at his last major girlfriend.  Not so uncommon except he had dated her over 20 years before I sat across from him nibbling on tapas.
  • One said and I quote “I still love my ex-wife.  My friendship is very close with her, even though she’s with someone else and if you or any other woman has a problem with that, I’ll always choose my ex-wife.”  This might be understandable if they had children together but they did not, and she lived halfway across the country.
  • Another guy told me that he was still in love with his ex-wife, even though she had told him she “never wanted to have sex with him”, and she had left him for another man.
  • The worst one was a man I had dinner with who went on and on about another female comedian he had corresponded with on OKCupid.  When he found out I knew her he said, “I find her fascinating and would love to have drinks with her.”  I blocked him from my phone on my way home.
  • I even had a man ask me for advice on ways he could get his ex back.  This was WHILE he was on a date with me.  I honestly felt sorry for him, but give me a break.

Even in my first major relationship right out of the gate post-divorce, my partner openly pinned away for the woman he had just dated before me.  She lived on the opposite coast and had never actually spent any significant time with him, but in his eyes she was somehow perfect.  Because she was inaccessible she was without flaws, yet an available woman who actually wanted him would never measure up.

This happens so often that now when I meet new guys I almost want to just ask him,

“So where are the bodies buried when it comes to your ex?  Do you hate her?  Do you still love her?  It doesn’t matter as hate and love are two sides of the same coin, so either way it’s bad.  How many times do you talk to her in a given month?  Are you actually divorced yet? Get it all out now, so I can leave before we might feel obligated to actually order dinner.”

When I see this pattern repeated it just reinforces every insecurity I have about myself.  All of the following go through my brain at the same time

  • Why is he so obsessed with her?
  • Why is no one obsessed with me?
  • Why am I OK for a backup but never the primary woman in any man’s life?
  • Why do some men obsess over women who treat them like garbage?
  • Do men only want women that they can’t have?
  • Why would he still want her if she left him for another guy?
  • I’m not good enough.  There’s something about me that makes me disgusting or unappealing.
  • Why did he chase me if he really wants her?
  • Would he take her back if she wanted to try again?
  • If I improved myself or changed my personality would that help?
  • What magic do these women posses?

I admit none of those thoughts are healthy or useful.  It’s my neurosis going on overdrive.  I find the constant struggle against “her” extremely demoralizing and a disaster for my self-esteem.  I can logically tell myself it’s not me, the guy is just hung up on his ex, and he’d treat most women like this.  I want to grab some of these men by both shoulders and scream

  • “She doesn’t want you anymore, let her go.”
  • “She’s so mean to you, you deserve better.”
  • “”If you think you guys still have a chance, then do everything you can to get her back, just leave me alone.”

The hardest are the men with children.  I don’t have kids myself, so I honestly have no idea how strange an intertwined a relationship with an ex could get.  Even if two parents absolutely hate each other they will still be deeply entrenched in each other’s lives for many years to come.  So far I’ve encountered men who bend over backwards to keep their ex happy, and men who constantly battle with their ex over every decision involving their kids.  Both are a nightmare for a new partner.  If a man is spending all of his energy towards the ex there’s nothing left for anyone else.

This rarely happened in my 20’s. Men that age just didn’t seem to get as worked up about a former partner.  It seemed like people were breaking up and hooking up with new partners all the time, without much second thought  Once we get older and put much more investment into a relationship, it just gets harder to let go. When our own personal “Happily Ever After” story gets crushed, we have a hard time imagining a new one.  In and ideal situation I would just pass out a psychological evaluation to every potential new partner with lots of questions about how they view their ex.  I know that would never really work, but it would certainly save us both time and energy.  *I’m not really serious, that’s sarcasm….but honestly it would make things easier.

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Dating After Divorce: Mr. My Bitch Ex-Wife

Before I get started with this one, I want to indicate that this problem is not gender specific.  Both men and women are equally obsessed with or tormented by a former spouse or partner.  Since I’m a woman, I’ll use the term Mr. My Bitch Ex-Wife but it could just as easily but a Ms. My Asshole Ex-Husband.

One of the biggest obstacles with dating after a divorce is getting past the damage caused by your former marriage.  It’s something I struggle with, as my divorce was incredibly traumatic.   I faced betrayal, lies, fraud, infidelity and was nearly destroyed both financially and emotionally.  I’ve been the very person I’m going to describe here, and I still struggle to get past it.  I’m not as bad as others, but I’ve got much room for improvement.

I’ve found on most dates I’ve had with total strangers, they usually blow their cover in the first 10 -15 minutes of the conversation.  It’s happened so often, that I could almost take a stopwatch and time the first comment that will issue a red flag in my head.  I’ve heard lines like the following before the waiter dropped off the menus.

  • My ex-wife is such a bitch
  • I hate my ex, she’s pure evil
  • My ex-wife is crazy, insane, psycho, etc.
  • Isn’t divorce hell, my stupid ex-wife ruined my life

For the rest of the date,  literally every topic somehow goes back to their ex-wife.  A drink reminds them of the bitch ex-wife, the food, my phone, my dress, a story from my past, my hair, it just doesn’t end.  The worst cases will demonize their former partners to such a degree, that I might believe their ex could be a danger to the public.. Their former partner is a complete raving lunatic, hellbent on destroying lives and impossibly cruel..  If I believed everything a Mr. My Bitch Ex-Wife tells me, then they were somehow a hapless victim who got tricked into marrying a she-devil who flipped out the minute their nuptials were final.

Now sometimes they could be speaking the truth.  Both men and women can unwittingly marry sociopaths, narcissists, serial cheaters, partners with untreated mental illness, substance abuse problems or violent raging tempers.  Marriage and relationships are a crap shoot, and most of us enter into them with the best of intentions.  No one has a crystal ball to see into the future and people do change their personalities, or deep-seated problems surface years into a marriage. Regardless, if their conversation revolves around stories about an ex, they’re probably not ready to date someone new. It’s doesn’t matter if they are beautiful, charming, funny or otherwise perfect, if they are that fixated on an ex there’s no room for a new partner. However there is some gray area here.  If you’re past the age of 35, you’re not going to find an age-appropriate partner who does not have some complicated baggage.  It’s hard for anyone to get past a major break-up or divorce, so it’s not unusual or unexpected behavior to vent about a former partner.  It’s also next to impossible to talk about your past if you have to block out 10 years or more to avoid talking about an ex.  No one is perfect but some warning signs to look for are the following.

Speak in absolutes – When they speak of their ex, it sounds as if they are describing a fairy tale villain.  There are no redeeming qualities, the person is completely evil, mean, cruel, or vicious.

Take no responsibility for picking their partner – Regardless of the circumstances of my divorce I do take full responsibility for choosing my husband.  Yes, he lied to me and was incredibly deceptive, but I chose to ignore several warning signs that could have indicated something was up.  I wanted to live in denial.  I didn’t want to face reality.

Portray themselves as complete victims – In some cases this is true, but how did the person react to abuse?  Did they take steps to get out of the marriage?  Did they fight back?  What did they try to do to change the situation?  In some marriages, especially ones with children, people can feel trapped.  What they do to save themselves or the situation is very telling. Even just standing up and calling out the abuse can be quite courageous and proactive.

Every ex is crazy – I knew one woman who literally claimed that all four of her ex-husbands tried to kill her.  The stories she told were fantastical, and she had problems keeping the details straight.  Anyone can make the mistake of marrying or dating someone with a propensity for violence, but it’s highly suspect if every former partner is unstable and violent. Either they love being in destructive relationships, or they are exaggerating their past.

Ultimately it comes down to what you are comfortable with.  If you want to take a chance on someone who spends half the date ripping apart their ex, then go for it.  You might be happier though with someone who actually wants to get to know you, and not treat you like a free therapist.  If he says the words “bitch” and “ex-wife” in the same sentence right after meeting you, it might be a clue that you’ll end up being the next “bitch ex” in his life he’ll complain about to someone new.

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Dating in New York City: The Rat Race Redefined.

Months before I moved to New York City I made the mistake of watching a documentary about rats in the city.  I learned rats could chew right through cement and squeeze their entire bodies through holes no bigger than the size of their skulls. Rats must constantly gnaw on anything in order to keep their always-growing teeth a manageable size.  Their jaw muscles exert a shocking 12 tons of pressure per square inch.  Rats spread disease, fleas and cause fires from chewing through electrical wiring.  In moments of extreme stress they attack each other and will even resort to cannibalism.   After that film, the mere sight of a battle-scarred super-sized rodent with a flesh tail would cause my heartbeat to quicken and stomach to churn.  I found myself in fits of panic if they got more than a few feet from me.

When my ex and I moved from Brooklyn to Washington Heights we discovered a fairly developed rat nest in the roots of a tree in the sidewalk.   In the rats would scurry from their nest across the sidewalk and into the alley of a building two doors down from our own.  We’d hear screams of people who had made the mistake of walking on our side of the street night after night.  My ex-husband counted as many as 20 rats at a time in the courtyard of our neighboring building.  We’d watch in despair as they would chew perfect tunnels through solid concrete the city poured over their nest..  Animal control repeatedly set poison traps, and laid wife mesh over the concrete and nothing seemed to stop them.

Then one night, out of nowhere my reaction towards the monstrous creatures changed.  I was coming home late at night after a comedy gig and saw one, all by himself sniffing around the subway platform searching for food.  He had half of a tail and large patches of baldness along with matted fur.  This rat wasn’t doing so well, and for the first time I saw desperation in his movements.  He just didn’t run around like every other rat I’d ever seen before, he seemed panicked and fearful.

I couldn’t help but see a part of myself in this poor dying creature.  When I first moved here, I was one half of a couple.  I had dreams and ambitions that always included the man I thought was the love of my life.  Fourteen years later after the terrorist attack on 9-11, a city-wide blackout, Hurricane Sandy, a devastating divorce, the premature death of too many friends, suicidal thoughts and crippling depression I found myself alone.  I’m not as young as I once was, my reproductive capacity shrinks by the minute and I’m deeply damaged.   In order to pay my bills I work constantly.  Some weeks I might get one day off, or work nonstop without a break for days on end.

There are those who criticize me for choices I’ve made, things I’ve written or said, and my “bad” attitude.  Of course they have no idea what goes on in my head, or how difficult it might be to come back after such a devastating loss.  Things haven’t completely healed and in the past six years I’ve rarely felt strong emotion towards a man for any extended period of time.  I don’t know if I’ll live the rest of my days alone.  In many ways surviving after the breakup has been harder than the split itself.  One day turns into another and nothing changes.

I get harassed on a daily basis with men leering at me, shouting out filth, blocking my path or even grabbing me on the street.   Most of the guys who express interest in me only want sex, and will literally not even touch me after the fact.  It’s as if I’ve left the room and might as well leave, which is usually what I do anyway.  I’ve numbed myself enough to stand it, and swallowed pride and emotions with the increasing dexterity.  If that’s what I need to do to survive then so be it., I survive, but only barely.

So when I looked at that rat, desperately hunting for food, doing nothing more but trying to make it to the next day I felt empathy for his plight.  I didn’t want to go near the poor animal, and I’m not kidding myself about wild urban rats. They’re a dangerous scourge, the city is right to try to eradicate them and control their numbers.  Regardless he was still a little life who never did anything but try to make it to the next day.  For reasons beyond his control he was born into a crowded metropolis and will probably die of starvation, poison, or at the teeth of another rat soon enough.  For the first time in my life, I had compassion for something I had once reviled.  Chances are he never ate another rat, or attacked a human, he was probably just an average rat living off a garbage and dodging subway cars.   I sat down on a bench a safe distance away from him and watched his darting and scheming until the next train came.

As much as I’ve been through, and as hard as things get, my struggles and pain have been a gift.  Had I stayed married and enjoyed the success of my ex-husband’s thriving career I might have never found empathy and compassion for that sad little animal.  I would take what I had for granted, and failed to see that every new day is truly a blessing.  I had to lose everything to become more human.  My life might not get easier for many years to come, or it could change in an instant. I’m just happy I’m still here and I don’t fear the rats anymore.

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Dating in NYC: Love and Real Estate

I’ve lived in New York City now for fourteen years. I’ve been single for the past six, and I started searching for a co-op about a year ago. I couldn’t help but notice the eerie similarities between hunting for real estate and looking for love. Both are rare and precious commodities. New York City’s vacancy rate hovers around 3% and never goes above 5%.  About 3/4 of all apartments are rentals, leaving only the remaining 1/4 available to buy.  Most of the apartments on the market are co-ops that require financial gymnastics, and approval of an overly scrutinizing board. Even if you find an apartment in your budget you still have to get  80% financing and then impress upon your soon to be potential neighbors that you’re a low risk addition to their building.

Dating here is not much better, especially for single women.  New York City has 150,000 more single women than single men.  It might not seem like a huge number in a city of 8 million but it’s enough to throw off the odds a bit.  To make things worse most New Yorkers work long hours, live scattered over five boroughs and have little disposable income to throw away at dating. I’ve found it’s best to not get too emotionally attached to any one partner or property.

I once was the only person to show up at an open house for a cute prewar newly renovated studio in prime condition. Just as I was about to start the long and arduous process of making an offer, an all cash buyer walked in before I had a signed contract and snapped the property out from under me.  I watched in horror as the same scenario happened again with other properties.  In dating, I’ve had a few amazing dates with men who seemed almost perfect only to have them vanish without explanation.  My text messages went un-answered, my emails ignored and I never knew the reason.

I couldn’t help but see the similarities and the heartache that went with both, so I devised a glossary of sorts of common terms used in NYC real estate listings and how they equate with the dating scene in New York City.

Prime Location = Is the trip between Astoria and Bushwick worth it? Can a man in the Bronx find love with a woman in Staten Island? Is Queens to New Jersey even possible? Finding someone on the same subway line = prime location

Low Maintenance Costs = Cheap date

All Cash Buyer = Partners that offer everything up all at once with very little drama and no strings attached. The downside is they could flip you. Just as quickly as they find you attractive, they’ve moved on. They can just as easily make another offer as quickly as they made the first.

Unit has pre-existing long term tenant = Married.

Board Approval Required = Facebook, Instagram, Twitter, Snapchat, LinkedIn – everything dissected and analyzed for risk assessment. Are you friend’s with an ex? Is your job stable? Do you post NSFW videos, sports clips or cat memes? How many friends do you have? Are your tweets too personal or do you post political rants? Do you change your status update 20 times a day? Do you hardly ever check your profile? Are your photos of landscapes, or of your family

No Board Approval Sponsor Sale = The person either doesn’t know how to use the internet or doesn’t care. No questions asked as long as you fit the criteria. You are dealing with a risk taker or at last someone over 50 who doesn’t understand this thing called “the internet.”

Move in Condition = Easy going personality, no glaring compatibility issues, similar hobbies and interests.

Needs TLC = Major emotional baggage – divorce, nasty breakups, children from a previous marriage. – Anything that might need fixing or at least managed.

Pet Friendly = Deal breakers or selling points depending on your allergies or your furry friends.

Building has Bad Financials = A date has bad financials – no job, huge debt, poor credit

Seller is Seeking All Cash Buyer = Just someone looking to hookup

Lack of Inventory = Are you a woman over 35? Then you know exactly what this means. Most men in your age group are married or at least coupled up. You’re going to have to look a lot harder for what you want, or settle for someone much younger or older.  It’s not as a big of a problem for men.  If you’re wondering why, it’s called babies, biological clocks and a patriarchal culture that values younger women over older.   Although no one is immune, both genders can have unrealistic age standards when it comes to dating.

As impossible as the New York Real estate market is right now, I’ve had far more luck finding a new apartment, then a partner.  Let me rephrase that for emphasis.  I’ve actually had an easier time finding an affordable apartment in a year than I have finding a partner in the nearly six years I’ve been divorced.  I’m not even kidding.  In my search for an apartment I had the help of an attorney and real estate agent.  I also looked EVERYWHERE from the far reaches of Brooklyn, to Queens, upper Manhattan and even parts of the Bronx.  I called and emailed at one point about 25-30 agents and saw as much property as I could possibly fit into my schedule.  There wasn’t much on the market in my price range but I viewed everything within reason.

I’ve basically tried the same approach to dating in that at this point I’ve probably been on at least 25-35 dates.  Most have been awkward and painful and a few men have had full blown meltdowns.  I’ve been out with men who complained about their ex-wives the whole time, bragged about their drug use, openly insulted me, or expected sex on the first date.   The vast majority of emails I’ve gotten on online dating websites have been from men under age 25 or guys looking for no strings attached sex.  Most of them men who do contact me never follow through with a date. So far nothing has worked, and I haven’t gone out with anyone for more than two or three dates in over five years.

For now, I’ll just settle for the apartment of my dreams rather than any prince charming.  Real estate is more stable anyway, it won’t have a midlife crisis and leave me for a younger seller, develop a substance abuse problem, grow mean and bitter and blame me for all it’s shortcomings, develop a gambling or ignore me and go play golf.  It may not cuddle at night but it will increase in value, and in the end I might get lucky and unload it to an all cash buyer.  I certainly couldn’t ask for such certainty with a new boyfriend.

My whole real estate search also made me ask some questions about myself.  I’m definitely a pet friendly unit with good financials and low maintenance, but one that needs some TLC.  I’d also say my board is fairly strict and rather picky of any potential candidate but the opportunity for a long-term investment is solid.  Now, if I could just find the right buyer, I’d be all set.

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