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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 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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Dating in New York City – The Death of Dating & Emotional Zombies

I sometimes think being single in New York City turns a person into an emotional zombie.  I don’t say that to insult single New Yorkers as I am single myself.  I have noticed though in the past few years that my personality has drastically changed when it comes to dating.  I used to get really worked about it, and now I’m a step away from comatose.  All emotion has basically been beaten out of me.  No one has physically attacked me of course, but any rough edges are now weathered down by a sea of apathy.  It’s as if the harshness of the dating scene washes over us like a thousand pieces of sand paper an smooths us down to smooth dullness.

After the first few dates, I blamed myself for being overly emotional or too screwed up from my recent divorce.  I was a complete emotional wreck and probably should have taken time off before dating, but it wasn’t just my emotional turmoil that was causing the problem.  It was an entire city devoid of authentic emotion. Not everyone, but most men  acted like the walking dead, ruled by their genitalia and nothing else. I was far more judgmental of this quality when I started out, then I realized it wasn’t so much a choice as a method of survival.  Like a nasty pandemic it spread throughout the whole city, neither gender spared.  I heard story after story from my male friends of women who acted the same way.  We were all reduced to little more than our zip code, our sexual preferences and lifestyles.  I was no longer a woman in my late thirties/early forties but Flatbush, straight, non-smoker with cats.  Everything else about me didn’t seem to matter anymore.

What caused this?  What turned an entire metropolis into the land of the emotionally dead?  Technology hasn’t helped.  Even though now we can connect in so many ways,  I can honestly say without irony that I’ve had more solicitations for cyber sex than actual physical contact.  When once a man might call me on the phone to chat, they now text. Communication reduced to broken phrases and emoticons.  Even typing in a complete sentence is too much effort for some.  Misunderstandings are common as tone is next to impossible to convey and sarcasm deadly.   Dating websites have evolved into  hook-up apps that promise little more than one awkward or thrilling evening to cut the boredom.

Eventually I’ve succumbed and became numb myself.  It must have been all the bad dates, the dick pics, the requests for immediate sex, the constant same day cancellations, and the judgmental pricks who think taking a train to Brooklyn is just too much to ask.  I officially gave up a while ago.  I’ve shut down all of my online dating profiles, I can’t even fathom joining tinder.  When I do date, which isn’t often, I find myself trying to smother any spark of emotions that are left.  I tell myself, don’t react, don’t care, show no weakness and maybe you’ll get through it.  Maybe if I’m dead enough, I’ll finally win at this game.

But in some ways my zombie infection is a good thing.  I used to put up with so much bad treatment.  When I would once make excuses for a man who didn’t text back, I now delete them from my phone.  I cut them off and don’t look back.  When a man is rude or snobbish about my type of employment he becomes invisible to me.  When a guy shrugs his shoulders at taking the Q train out to central Brooklyn, I erase him from my brain.  I have in many ways become the person I feared.  It’s not that I don’t have empathy for others, it’s just survival.  In a city where anyone can walk away and return to instant anonymity negative behavior thrives.

I’m less judgmental of people just snapping and hooking up with the next person who offers.  I understand the need for human touch that lies within us all no matter how hard we try to bury it.  We try to control it completely but all the pornography and our sexually heightened culture can’t control the need to just be next to someone if for a moment.  I’ll shuffle back to my own corner of Gotham and try to smother the beast inside who cries out for more.  I let the sea of apathy wash over me again and the numbness is comforting.

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Top 10 Rules for Dating in New York City

It’s been five years since my marriage completely disintegrated.  I found myself suddenly thrust back into the dating pool at age 36.  My single friends tried to warn me, but I honestly had no choice.  My marriage was dead and there was no saving it.  I made every dating mistakes a few times.  I’ve evolved from overly emotional, clingy and starry-eyed to cynical, jaded and emotionally bereft.  I keep hoping things will get better, but they never improve.  I’ve tried online dating to no avail.  Most of the guys online never follow through with dates, so I find myself carving out precious time only to resort to sitting in a coffee shop by myself or watching House of Cards on Netflix when my date cancels.  You know it’s bad when you think to yourself that doing business is easier than dating in this town.  I’ve honestly been treated better in most professional relationships, than I ever have been in romantic ones.

So I’ve devised this list.  It pretty much encapsulates what’s become of dating in the city that never sleeps.  From what I’ve heard this across the board for men and women of all sexual orientations and gender identifications.

How to Date in NYC


1. Lower your expectations – I’ve gone from thinking “Maybe I’ll get remarried someday” to “Just answer a simple text message, I only sent you one in the past three days.”


2. Become numb – Get rid of all of your highs and lows as they will not serve you.


3. Show no weaknesses – Don’t let on your hopes and fears too soon.  Show no signs of insecurity.  These things can come later, but since this person probably won’t stick around for any length of time, they don’t need to know any of this.  Put your game face on and keep it on.


4. Expect rude behavior – If you send a simple “What’s up?” text, do not expect a response.  This is after you’ve been out with the person and seen them check their phone every ten minutes. Expect last minute cancellations, constant excuses for why they aren’t available and angry rants about ex-partners.  These are all par for the course.


5. Completely give up on the notion of age appropriate – I’m hit on by men as young as 18 up to around 27 or 28, then the next largest demographic is mid-fifties.  I can’t explain this, but I’ve given up trying.  I just go with what’s offered.


6. Google everyone – Knowledge is power.  Don’t stop at google.  Youtube, Facebook, Twittter even Instagram hold few secrets.


7. Trust no one – Because we live in a city of strangers, a person has to earn your trust before you just believe anything they tell you.  “I had to work” could easily mean – “I was hooking up with one of my other regulars” You might eventually trust your partner, but until then, take what they say with a grain of salt.  Note inconsistencies, never assume they are legit.


8. Get used to the phrase – “I’m just so busy” – You’ll say this yourself.  But you will also hear it as an excuse for everything.


9. Get used to the phrase – “Oh but you live so far away.” New York City is a big town.  We sometimes meet in the middle of this Metropolis in Manhattan.  Only later do we realize that a Bronx to Queens commute is just impractical.  Although some expect to put in absolutely no effort whatsoever.  Basically they will only consider dating you on a regular basis if you live two or three stops away on the same subway line they take every day.


10. Have fun with showing off your dick pic collection, and you’ll get one…trust me you’ll get one. – I don’t know if there is a lesbian or straight woman equivalent, or if this phenomena is as common with every sexual orientation.  I only know that straight women and gay men easily collect dick pics and full frontal nudes. I’ve scrolled through dozens in my gay friend’s phones. I’ve gotten several and I never once requested – “Please send me a photo of your cock. Preferably a self-portrait taken with your phone.  A bathroom shot would really be something special!”  I’ve also gotten requests for photographs of body parts or my mouth wrapped around dildos and various objects.  I’ve never complied. Who said romance was dead?


11. Accept your fate as a crazy cat lady/eccentric bachelor. – I know this brings us to eleven.  For men I guess the crazy cat lady equivalent is the weirdo eccentric bachelor.  We all know a few.  The guys who never got married and have that apartment just full of strange things from their youth.  It’s small and rent stabilized and they’ve lived there for years.  They’ll probably die there but they won’t be eaten by their pet cats, instead someone might stumble upon their mummified corpse after neighbors complain of the smell or they are a final no-show for their eviction in housing court.  I hope that’s not my fate, but things aren’t looking so good lately.

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Dating Online – Why a Young Cub is not always that attractive to a Cougar

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The day I turned 40, something completely surprised me on my online dating profile.  I thought that once I reached my midlife milestone birthday, the amount of email would slow down. I was surprised when I saw more traffic than ever.  The bulk of interest came from much younger men. Suddenly 19 and 20-year-olds were sending me things like,

“What’s up? U R Hot. Do U like younger guys?” – Always hysterical to me, since the young ones often use text speech and insane word substitutions that drive me crazy.

“I really love older women.  We should hang out sometime.  Let’s get a drink” – I’ve gotten these from men who aren’t old enough to legally drink alcohol.  So either he’s got a fake ID, or we’re drinking coffee.  I guess I could take the risk of being arrested for giving alcohol to a minor, that would be living life on the edge!  Maybe they are asking me out BECAUSE I can buy them liquor.  Who knows?

“I know you’re a lot older, but I’m really looking for a serious relationship” – I’m not kidding, I’ve gotten several emails like that one.  Are they serious?  I have no idea.  Do they have Mommy issues?  Probably.

“I’m going to start college in the Fall. I love to go snowboarding, and play video games.  Let’s hang out!” – I assumed he lived with his parents and was still in high school.  So technically he’s legal, but honestly who in their right mind would think that’s a good idea? Someone must have written a self-help book that advises young men to search for women 40 or older on dating sites.  After 40 we’re more desperate, we’ll pounce on a young eager kid.  When I’ve complained about this deluge of barely legal would be suitors, some of my male friends get extremely upset with me.  I hear things like,

  • Well I would dream of getting hot 19 year olds in my inbox
  • Score! You have teenagers hitting on you.  I’d tap that!
  • How could you complain about young guys?

Again I know this might sound shocking to some, but men and women are extremely different creatures.  Most women in their 40’s don’t want to date men over 20 years younger.  Of course there are exceptions and age and maturity don’t always go together.  If two people can find love in this world and they have a twenty year age difference, then more power to them!   But usually most of those 19 year olds I get in my inbox aren’t exactly “hot young studs”.  The really good-looking younger men, probably have a surplus of attractive, hot young women.  And I’m not talking about a 30-year-old with a 45-year-old.  At that point both parties are adults, and although the age difference is great, it’s not the same as a 19-year-old man hitting up a woman who could be his mother. Even though a 19-year-old is legally an adult, most are basically children.  I have theories about why I keep getting these requests, the younger men think an older woman could:

Teach them about Sex – Some women might get off on this, or think this could be a lot of fun.  Personally I don’t want to train anyone. The thought of having awkward or bad sex with someone who doesn’t know what he’s doing is not exactly my idea of a good time.

Take care of them Financially – Some don’t even hide this, and will say it openly.  My favorite was from a 29-year-old.  He somehow just assumed I would was rolling in it because I was a whopping 11 years older than him.  If only being 40 magically brought financially stability. In his case we discovered he was better off than I was.

Take care of them Emotionally – Mommy issues.  Some guys really do feel more comfortable dating someone who takes on a more maternal role in their lives.  To each his own on this one, but not every woman is going to WANT that arrangement.

Need to be Dominated – This is true of men at any age, but the power dynamic does get a bit skewed with a large age gap.  An older woman is probably going to have more life experience and more relationships under her belt.

Drawbacks to younger men

  • Aren’t financially secure
  • Immature
  • MIght live at home or with multiple roommates
  • Have totally different interests and lifestyles
  • He might not get along with your friends, you might not get along with his
  • Probably won’t want kids right away
  • Less likely to stick around long-term
  • Text speak, totally different communication skills – The younger ones don’t call, they text, tweet, IM and Skype.  It’s a whole new world of abbreviated speech that can be a bit unnerving to women who write in full sentences.
  • Porn educated – Sorry boys but this one is so true.  I’ve found with men closer to my age that sex is far less influenced by pornography.  Younger men don’t seem to understand that porn is a FANTASY and that most people don’t try to reenact porn scenes every time they have sex.
  • Lack of sexual experience

Of course age is just a number and emotional maturity and numerical age do not always go together.  I’ve met plenty of immature men in their 50’s and 60’s.  Some May December romances work out beautifully and there are no hard rules to what makes a relationship work.  I have several female friends who are older than their partners. The older two partners get the less an age difference matters.  A 30-year-old with a 45-year-old is something else entirely than a 19-year-old with a 34-year-old.  Once a person is well into adulthood, they know who they are, what they want and have a reasonable level of maturity.  A kid who is 19 or 20 however is just trying to figure these things out, they could be so easily manipulated and crushed by an older partner of any gender. I wish my male friend’s fantasies were true, and the hot young 21-year-old men were lining up in my inbox, but that’s just not the case. Regardless, I want a partner who is an equal, and it’s difficult to see a kid in college as a peer.  So until then, much to the disappointment of my male counterparts, I’ll continue to turn down the young ones who hit me up.  I would rather not be the cougar who devours willing cubs.

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Dating in NYC: Dating in the Land of Zero Effort

Online dating profiles reduce humans to commodities.  Instead of nuanced individuals with provoking personalities, we transform into a collection of photos and vital stats such as: height, age, body type, diet preferences, religion, political views and our favorite books and movies.  In New York City online dating profiles should just include a few photos and a zip code, because honestly that’s all that really matters for so many singles.  If you live in Brooklyn, trying to date a person in Queens could be considered a long-distance relationship. Staten Island and the Bronx might as well be in other states, and New Jersey is the vortex.  It seems much easier to get into the Garden State then it does to get back.  Even though over 19 million people live in the New York City metro area, commuting via subways, buses and cramped highways is challenging.  Even when I meet men offline, most conversations start like this:

Guy: “Where do you live?”

Me: “Brooklyn”

Guy: “What neighborhood?”

Me: “Flatbush”

And then I see the facial expression that says everything I need to know.  Their eyes will squint, their brow will cease and it looks like they just smelled some week old Indian food.  No one has ever lit up and smiled after hearing it.  Some men have actually broken off the conversation after the word ‘Flatbush’ and walked away.  They’re hardly subtle about their complete disdain for my section of NYC.  On online dating services, things are much worse.  One man went so far as to indicate on his profile, he was only willing to consider ladies who lived on the “L” train, or within a short biking distance.

According to the latest census estimates here is how the city breaks down

  • Brooklyn     2,565,635
  • Queens       2,272,771
  • Manhattan   1,619,090
  • Bronx           1,408,473
  • Staten Island   470,728

Given the odds, I should have the easiest time of it.  The problem is Brooklyn is huge and the subway system doesn’t easily connect every neighborhood.  So to get to Mr. L train, I would have to jump on the Q train, take it into Manhattan, then transfer to the L train and take it back into Brooklyn.  My journey would last an hour maybe 45 minutes, which is just too long for most folks in this metropolis.  The Bronx and Staten Island are like different countries to me, and my commute to some parts of Queens could take over two hours.  When a guy hits me up and lives in New Jersey, he’d better live in Hoboken, Jersey City or another part of NJ that is easily accessible via public transportation.

I’m not a huge fan of my neighborhood as it has a higher crime rate than others and is a bit farther out from Manhattan, but my rent is much cheaper and my apartment is larger than most.  By most Manhattanite standards, my ‘hood is the middle of nowhere.   From what I’ve found the most ideal location is Manhattan, as its central location makes it easier for anyone in the outer boroughs.  Although anywhere above 125th Street is the mysterious hidden borough called ‘Northern Manhattan’.  Just as it’s more difficult to get furniture delivered to neighborhoods like Washington Heights, Inwood and Spanish Harlem, it’s also harder to get anyone to travel to the far reaches of the Island.

I guess I just magically need to make more money so I can afford to live in one of the most expensive places on earth.  I’m not expecting much, I just get sick of always being stuck at home with my cats watching “House of Cards” on Netflix.   In my neighborhood I’m mostly hit on by teenage drug dealers.  I’m not speculating on their illegal activity, I’ve seen them openly sell drugs right in front of me.  The average age of the guys who yell “Hey Baby” at me is about 16.  Since Flatbush is hardly hip, most of the age appropriate men who live here are very much married or living with someone.  I just don’t find a lot of single men age 35-45 anywhere, but I especially don’t run into them in my part of Brooklyn.

I think this is why those hook-up apps like tinder are so popular.  They really do take away all effort completely.  Want free sex from a somewhat attractive female who is easily accessible, in more ways than one?  Just swipe right and hope she does the same.  I still refuse to get that desperate, until then I will remain in Flatbush and hope that somehow a guy might want to ride the train for more than 20 minutes to see me.  Or maybe I’ll get a job managing a hedge fund tomorrow and move to a mansion in the Hamptons. When I live in my sprawling estate I can pick up guys at the local tennis court, or while riding the ponies in a co-ed polo match.  Anything is possible I guess.

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Dear Stranger from out of town, I’m not an unpaid prostitute.

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Online dating is the social experiment that keeps on giving.  I’m always amazed at hidden agendas it reveals.  If I select that I’m looking for casual sex in my profile, I will literally get over 100 emails in a 24 hour period.  Men are looking for no strings attached sex, but few will be completely open about their intentions.  One of the strangest phenomena are men from out-of-town who seek sex with New York City women.  My inbox overflows requests like these, yet nothing on my profile indicates that I’m looking for hook-ups.  A typical email goes like this:

I think you’re hot. I’m going to be in New York City next week and I’d love to hook-up if you’re game for that sort of thing. If you aren’t, then my apologizes.

The straight forward approach is a bit unnerving, but they are easy enough to dismiss.   I always admire anyone who has the courage to ask for what they want.  As I’ve said many times on this blog, I wish more men were open and honest.  For every email like that one, I get about 10 of these:

I really think we have a connection. Even though we haven’t met, I can tell from your profile that you’re a caring and loving woman. Something about your eyes, and smile are so inviting to me.  I also think we have a lot in common, and we’d have a great time together.  I’ll only be in town for a week, and I really need someone to show me around the city. I know I could just sit in my hotel room in between my work, but I’d rather spend it with someone special like you.

Those make me want to vomit. It’s also an obvious cut and paste.  A guy will send the same email to dozens of women hoping one will bite.  My profile is mostly random movie quotes.  A savvier man will comment on the films I’ve quoted, or at least acknowledge that my profile is slightly unconventional.  Talking about my eyes, smile or the many things we have in common is intentionally vague.  Every woman has eyes, and most are smiling in at least one photo – so I guess a few might fall for complete drivel like that.  Others might realize the guy is a total phony but they think he’s attractive enough for a one-night stand.

Then we have the truly slime inducing ones:

Look, I’m going to be in New York City next week.  I’m going to be extremely busy.  Maybe if you’re hot enough in person, I’ll make some time for you.  You won’t regret it but you’d better be hot, or forget it.  I’ve got nine inches of pure manhood and I love to make hot chicks moan.

Luckily men like this are rare.  When I’ve gotten emails like these I’ve responded, “Why aren’t you on tinder” or “Hire a prostitute” or “I don’t need an out-of-town STD.”

Usually the men who proposition me for such liaisons aren’t exactly drop dead gorgeous, but a few have been.  I’ve still never taken the bait.  I’m not comfortable with these situations for a number of reasons.

  • Are these men married? Who knows?
  • Safety issues – Theft, sexual assault or worse
  • Drugs – Will I be slipped something that will knock me out?  Will the man be blazed out of his mind?
  • Privacy – Photographs, video, webcams – technology has gotten so small anything is possible
  • Unusual requests, unexpected kinky sex, inappropriate boundaries
  • BAD SEX

The last one is in all caps for a reason.  Sex with strangers is like rolling the dice, you really have no idea if you are going to have a steamy, hot night of passion or an awkward, uncomfortable evening of disappointment.  Simply put sex with a total stranger, is sometimes not just mediocre but downright scaring.  Most of the time when men have sex, they’ll at least have an orgasm.  Any woman knows we aren’t always as lucky.  A selfish or unskilled lover can make the entire enterprise one long night we wish we could forget forever.

Women also get hit up for free sex all the time.  If I want no strings attached sex I can probably get that from someone I already know and trust a bit.  I also don’t need a girlfriend or wife tracking me down weeks or months later when they’ve discovered an “affair” which was really just a random hook-up.

Overall these requests make me feel like I have no value.  A sex worker might put up with strange sexual requests, a selfish one-sided lover or an uncomfortable experience.  A prostitute at least gets paid, and usually quite well for their services.  Of course some women love the turn on of having sex with a total stranger who they will never see again.  However most women who want hot sex from out-of-town men are on hook-up sites like Adult Friend Finder and Tinder.  It’s a bit of a leap for any man to assume all women want this type of sexual experience.

Basically. if you want to buy shoes, don’t go to a hat store.  Plenty of women are waiting for your emails you just need to look for them on sites specific to your search.  Sex workers are also always available, they might be pricy but there’s nothing wrong with an agreed upon transaction between consenting adults.  Never assume the average gal on OKCupid or Match.com is waiting for your “Nine inches manhood.”  We know it’s probably closer to six inches anyway. 🙂

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Dating in NYC: The Honest Sinner vs. The Phony Saint

Disclaimer: To protect the identity of the men involved in this article – I am leaving out some specifics about them and these events. I will not disclose anything more about them publicly.  I don’t really want to get sued, or have anyone accuse me of slander…I didn’t write this to attack anyone – just as a cautionary tale.

Why do so many people deceive others when it comes to dating? I’ve heard countless stories about men and women who lie about their age, job, marital status, a previous divorce, a live-in partner, even children. People also hide their true intentions. They might act like they are looking for a serious relationship when they are really wanting no-strings attached sex. A man or woman might also pretend they want a casual relationship when he or she is secretly hoping for a committed one. I’m a huge advocate for truth. Honesty will get a person father than secrets and lies. I have two examples in my own personal life that illustrate this perfectly.

The Honest Sinner – An absolutely beautiful man who was over a decade younger than myself and someone I knew casually. When he approached me he was upfront.  He was looking for a casual sexual encounter, no strings, no expectations. Before our hook-up, he even sent me a text with the rules of engagement. It wasn’t exactly romantic, but I knew he wouldn’t try to coerce me into anything I didn’t want to do. I weighed my options, and considered I would take him up on his offer. It wasn’t just that I found him incredibly handsome, I also genuinely appreciated his candor. We ended up meeting, more than once, and the sex was great. I didn’t care if he was hooking up with anyone else, as I never really saw him as much of boyfriend material due to our age difference. I also knew he didn’t have a serious girlfriend so he wasn’t cheating on anyone. There was never any pretense. We didn’t go on dates, and neither one of us indicated that we wanted more out of the situation. I decided to cut it off when it wasn’t working for me anymore, but I actually grew to like him as a person. Sometimes these arrangements can lead to all sorts of misunderstandings and misery but in this example it worked out. His looks were definitely a factor of why I had a casual relationship with him, but his honesty is what sold it. Had he been sleazy or deceptive I wouldn’t have gone near him.

The Phony Saint – A moderately good-looking guy who I thought I might want to date seriously. He was closer to my age, had a good job and was extremely well-educated. He overall was a much better match for me on paper, and I was physically attracted to him. We seemed to get along well, but I barely knew him, so I honestly didn’t have strong feelings either way.

Things went South on our second date when I made the mistake of going back to his apartment. Within minutes he got extremely physical and I felt uncomfortable. His sexual energy made me feel like some sort of live action porn doll – and I just wanted it to stop. My instincts were correct when right before he actually tried to have sex with me, he called me Gillian instead of Juliet. As soon as I saw the condom, I shut everything down. Then I completely humiliated myself and burst into tears. It honestly was the first time I can remember, since maybe college, when I have had a total meltdown while on a date. I was mad at myself for letting things get this far, and I felt like a total idiot for crying. Deep down I knew something was incredibly inauthentic about him so I asked, “Do you do this all the time? Is this what you do with women?” He looked at me sheepishly and said, “Well yeah. I’m basically a child, I can’t have a serious relationship.”

This man had a professional job and was in his mid-thirties. He had also asked me out on a date, he wasn’t upfront about wanting just a hook-up. Unlike the Honest Sinner who kept all his correspondence sexual and to the point, The Phony Saint laid it on thick with multiple emails and texts as if he had some real interest in me. He even claimed to have looked me up online. When I point-blank asked him, “Which videos did you watch of me?” he responded, “Um, two. One of you getting interviewed on television and another one – I don’t remember.”  Now I don’t know how he couldn’t recall a short video he claimed to have watched just the day before, but I really didn’t care.  I knew he really didn’t really give a damn about me when he called me by the wrong name, and treated me like some sort of masturbation toy.

For the next extremely awkward hour, or so I apologized for crying while he begged me for various sex acts.  Even at the time I was unsure why I didn’t just walk out.  I got repeated inquiries from him to “jizz on my ass, stomach or tits”. He actually used the term “jizz” and seemed shocked that I had no interest. I might have honored his requests if I actually liked him, or if we had sex, but at that point it was just pathetic. I was just in shock that things had gone so badly so quickly and I wasn’t really sure what to do.  During all of this he danced around the room naked while speaking to me in a sing-song jokey way. I guess he was trying to cheer me up, but it just made him lose any remaining dignity. He then offered me leftover take out from his fridge.  When I say leftover takeout, I mean takeout that was at least a day old if not older.  I told him I didn’t want his “used food” and I refused to drink anything.   Any spark of sexual attraction I had towards him vanished, but I also calmed down and realized I was in no danger.  Things got even stranger when I realized he seemed to enjoy being chewed out by me. The Phony Saint just became a test subject to me of sorts. Thankfully I was completely sober, but my sobriety just meant I would remember every horrible detail of what was now, the worst date of my life.

So which man got what he wanted? The Honest Sinner got free sex from a consensual enthusiastic partner. The Phony Saint experienced an extremely embarrassing and sexually humiliating evening. If I could scrape that night from my brain I would, and yes it will make great material for my stand-up, but I have SO MUCH material already. HA!!!!!! I would have much rather had a lovely evening than another horror story to share onstage. Had he been honest from the beginning, I probably would have turned him down for sex as I get offers for that from total strangers all the time. The Honest Sinner was someone I knew already and that factored into my decision to hook-up with him. But even though I would have turned down the The Phony Saint, plenty of other women would have taken him up on the offer. He was good-looking, had a nice build, a great job and his own apartment – he had plenty of qualities that would get him laid in New York City.

The moral of this story: When in doubt, just tell the truth – everyone will be much happier for it, and no one will end up dancing around the room naked begging a women to let him – jizz on her butt.  Also, never call a woman by the wrong name when you’re trying to seduce her – it’s just bad form.
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Dating in NYC: Top 10 Tips for Dating Multiple People

Before I even tackle this subject I will openly admit I’m a solidly monogamous person.  As I’ve written before the whole idea of multiple lovers, hookups and sexual relationships with near strangers baffles me.  I can’t keep several plates spinning while I’m trying to write this blog, work on my memoir, get stage time in New York City and pay my rent.   I’m writing this though because this issue comes up all the time, and I’m annoyed that most of the articles I’ve found about this topic are written only for men.  I’ve based these tips on experiences I’ve had and what a lot of my friends have gone through.  I not advocating for any style of dating, nor would I say this would work for every person.

There are many variations on dating multiple people, too many to list here really.  The key to having multiple partners should NOT be about lying, sneaking around and deception.  Lies are evil.  As I have said before:

I would rather have an honest sinner than a phony saint.

The following are just guidelines.  It’s really about what any two people are comfortable with in any partnership.  If you only have sex with a person once, they really don’t need to know much.  But if you are seeing more than one person on a regular basis, communication is key to keeping everyone happy.

1. Let a new partner know early on that you are not looking for a sexually exclusive relationship: Of course this can change as the relationship develops.  Neither partner should assume though that a casual open relationship will turn into a committed monogamous one. When in doubt – communicate.

2. Avoid getting involved with people who aren’t also honest with their primary partners – A friend who has been polyamorous for years put it to me this way.  “I avoid being the ‘other’ woman.  If a man tells me he is in an open marriage, I tell him I will have to speak to your wife about this, just to make sure”  It might sound crazy, but if the couple is in an open marriage, this sort of request probably happens to them all the time.  It’s better to make sure everything is above-board, before you find some woman calling you a home-wrecker or threatening to kill you for sleeping with her husband.

3. Don’t assume one lover wants to hear details about any others – Some partners honestly may not mind this, but not everyone is different.  One woman might not want to know that another regular partner is younger, thinner, lives closer to you or has a cat.  If these relationships truly are separate, then there is no reason to share this sort of information.  Simply establishing that you are not exclusive is usually enough.  If you want a change in your relationship, then let your partner know.  NEVER ASSUME ANYTHING! 

4. Always use protection – If you are having sex with multiple people – DON’T BE AN IDIOT.  Use condoms and practice safe sex.  Other than the usual STDs we all fear, there is a strain of antibiotic resistant Gonorrhea going around New York City that is all sorts of awful. Spreading STD’s is irresponsible and reckless.  If you want to have condom free sex, then maybe you might want to find one primary partner and at least use condoms outside of the main relationship.

5. Beware of Social Media – If you tweet naughty messages to one woman know that anyone can see it. You don’t know who knows each other or which partner might be a regular cyber sleuth.  Facebook profiles are even more transparent – comments, likes, even old conversations with partners are there for life unless you remove them.  A simple comment like, “You are so beautiful” could get you in trouble if you post it where another, more neglected lover, could see it. Basically you have to treat all comments on social media as if you are standing on top of a mountain declaring them for the universe.  The internet holds no secrets.

6. Don’t treat you casual lovers like girlfriends/boyfriends – Again there are no hard rules to this, as some polyamorous relationships are anything but casual.   This is the number one complaint I get from both men and women about casual relationships.  You can’t expect someone who you see only for sex on occasion to get that emotionally invested in you.  They aren’t going to necessarily want to meet your friends, go to social functions with you, listen to your neurotic ramblings or bring you chicken soup when you get a nasty cold.  When these lines get blurred, people are more likely to get their feelings hurt.  Anyone can have a primary relationship and still have multiple lovers on the side, but not without some boundaries first.  You should never assume a regular hook-up is a girlfriend, or even wants that role.

7. Treat everyone with respect – This should go without saying in every dating situation.  I’ve seen a lot of alarming language on dating sites, where a man or woman will go on and on about their primary partner and then send an email that is just rude and inappropriate to a total stranger.

8. Don’t make anyone feel like they are last on your list – This might be OK with some partners, but overall you don’t want to make a person feel like you literally called up three or four people before you decided to settle on them.

9. Don’t complain about other lovers – This is just rude behavior.  If a woman complains to a partner about another man she is seeing, he is likely to assume she will turn around and do the same thing to him.

10. When in doubt communicate – Of course you can lie and sneak around, but there is a good likelihood that you’ll get caught.  When you get caught a betrayed lover might slash your tires, show up at your workplace and scream “Whore” as you walk down the street, stalk you or one of your other partners, text you incessantly for hours, post naked photos of you online, write Facebook statuses trashing your name, or even threaten you with physical violence.  Deception brings out the worst in people.  Some people are emotionally unstable, mentally ill, cruel, narcissistic or have deeply entrenched personality disorders.  No amount of open communication can prevent a person from reacting in a completely irrational or psychotic way.  However a string of lies is more likely to make a perfectly well-adjusted human being buy a ticket to a place called crazytown.

It’s really up to you and your partners – Other than practicing safe-sex and respect, it’s really up to each person.  When in doubt be open and COMMUNICATE. Some of the biggest problems in any relationship come from not understanding what both partners want.

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