Dating After Divorce: Becoming Comfortably Numb


I wondered when it would happen, then a few months ago, it hit me.  After countless bad dates and a dating scene that feels like a wasteland, I’ve finally become comfortably numb.  It’s not what I expected.  I thought I would be more negative and more jaded, but it’s honestly somewhat comfortable.  My expectations have just hit rock bottom.

When I first left my marriage I was completely unprotected.  My heart was overly sensitive, my mind ravaged with depression and my instincts set at high alert. I needed to calm the beast, or I never would have survived. I used to cry after bad dates, usually on the subway home.  As soon as I would just sit down, I’d mildly lose it.  I don’t think I had unrealistic expectations.  Multiple bad dates had trained me not to think beyond the first encounter.  Then on the rare occasions I had a second date, I taught myself not to get too excited.  I’ve only made it to three dates with one man.  We had hardly gotten serious, we hadn’t had sex yet when he had a slight meltdown.  In his case, I don’t think it had anything to do with me.  From what he told me, he had some seriously unresolved issues with his ex.  Unresolved issues with exes is just a reality for people over 35.

Some guys would rather remain virtual.  I sort of “dated”  a guy who just wanted to email.  He claimed he wanted to see me, but then created countless obstacles.  I lived in Brooklyn and he lived in Manhattan, so it shouldn’t have been that difficult.  He also wasn’t over his ex, and I suspect was still trying to get back together with her.  I’ll never understand why I kept talking to him, or what was going on in his head.  I found out months after I gave up, he found a good match and they are inseparable.

I’ve had a few casual flings.  I forced every jealous atom inside of me to stay cool.  Hooking up with guys when I knew they had other women in their lives, wasn’t easy.  It really took Herculean strength to not react, to tell myself that it didn’t matter, we weren’t serious, this won’t lead to anything. I managed to stay calm, but inside I was miserable.

They haven’t all been bad.  I had a strong connection with one guy.  We found out on the date we were both straight spouses.  His wife left him for a woman, and I thought that maybe our shared experience might work to our advantage.  Despite obvious warning signs that he was clearly not over his ex-wife, we made out in his car for over an hour.  It was highly unusual for me, as I usually don’t even kiss a guy on a first date. Then he completely blew me off.   I guess the situation was too much for him, I don’t know.  I can’t remember his name or face.

Now I still have a few men who hover but do little else. They might send a dick pic, or a request for sexting that will lead absolutely nowhere.  I’ve learned I’m not the only recipient for their x-rated self-portraits.   If I say I’m interested in something more, they tend to bolt.  Of course I still get harassed on the street by any number of men of all ages.  I guess that might end when I have to use a walker or cane to get around.

The worst was my rebound relationship, something I never should have gotten myself into.  It was completely exhilarating, but ultimately soul crushing.  I had so many conflicted feelings towards him, at least two years after the fact.  Now I don’t see him.  I have no idea what’s going on in his life, and I have no desire to find out.  I harbor no ill will, but I also don’t want any contact with him.

I’ve become someone I would have never recognized five years ago.  But in a way it’s not completely awful.  It’s not what I thought it would be.  I’m not angry or bitter, just numb.   I take everything men say and do with a grain of salt.  So what if the guy sent me several texts in a row – It doesn’t mean anything until he backs it up with actions.  I rarely text anyone because I can’t stand being blanked back.  I would rather just have nothing than the feeling of being ignored.

I just stopped caring.  So what if the guy from OKCupid sends me eight emails only to cancel the same night as our date.  I don’t even blink if some man rants about his “bitch ex-wife” for half the date.  It no longer surprises me, if he insults what I do for a living, or complains about my crappy neighborhood. This is dating after 35 in a city where only the strong survive, and you’ll be judged on everything your job, neighborhood, past relationships, pets, hobbies even your hometown.

Some of my dates have been so rude and so horrible that if I recreated them in a movie, I would be accused of being too fantastical.  I try to keep an open mind, stay positive and keep moving forward.  My horrible experiences have given me armor.  I rarely have crying fits on the subway anymore.  I’ve just learned to block the disappointments out.   Most divorced people never think they are going to end up like this.  Few of us expect this as our future.  If we learn more from our failures, I’ll be a genius by the time I finally meet a compatible match.  🙂

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Online Dating: We just aren’t that into you


This is for everyone who tries online dating.  I’m going to write it from a woman’s perspective, but I’ve heard numerous stories from men about this very universal problem.

On the first or second date a lot of guys assume the following

  • I’m madly in love with him
  • I want to have sex with him as soon as possible
  • I have an overwhelming desire to make-out or touch him
  • I’ve somehow had this long-enduring crush on him and FINALLY got up the nerve to ask him out
  • I’m completely sold, my date is the man of my dreams
  • I think he is my next husband, or I’m already dreaming of our nuptials
  • I just called my mom to tell her about how excited I am about this date

None of this is true.  I’m sure there are some women who really do think that when they go on dates with men they’ve met online.  There are always crazy people out there, but honestly most of women that I’ve talked to about online dating feel the following:

  • He doesn’t look like a serial killer
  • He’s alright, I hope he looks like his photos
  • I guess I could go out with him you never know
  • He sorta looks OK
  • He has nice eyes
  • He isn’t allergic to cats and lives in Brooklyn

That’s about as deep as it goes.  HONESTLY.  And this is usually what goes through my mind before a first date with a guy I met online:

  • Don’t let this date stretch on forever
  • I can’t spend a lot of money
  • I hope he isn’t psycho
  • I’m not sure if I even want to go through with this
  • I don’t want to put too much effort into this because most of these dates dont’ work out
  • Please don’t stalk me after this date
  • Maybe it’ll work out and I’ll go on date #2 with this one.

I actually do try to keep things positive, but this isn’t my first time at the rodeo.  I keep my expectations nice and realistic.  So when I meet a man online and he decides to take things physical way too soon, I just hate him.  A hookup site such as Tinder or Adult Friend Finder might be quite different, but most people don’t regard dating websites in the same way. If they are just looking for casual sex, they usually indicate it on their profile, or they should.  Because I’ve never had strong feelings towards a first date, I usually assume they don’t have strong feelings towards me.  No one really knows if there is actual attraction or chemistry until they physically meet.

I have had guys grab my hands, or put their arms around me when I have no real attraction to them, and it just makes me uncomfortable and I’m never sure how to handle it.

Where does this misperception come from?  I’m not sure, but I think it’s people of both genders assuming online dating is like regular dating.  When you were 20 years old, the sight of the cute boy in your biology class could make you weak at the knees.  The two of you would chat a bit and eventually the guy would finally make his move and ask you out.  Within hours you were cuddling in the booth of a diner asking about his favorite food, and his nickname in high school.  Online dating is just not like that. It’s two total strangers who thought from a few questions and photos that they MIGHT be attracted to each other.  With online dating you don’t even get the sense of physical chemistry you might get when meeting a guy in a bar.  It’s just so inorganic and actually goes against our instincts in almost every way.

Sure we know beforehand that the guy isn’t allergic to cats, lives near us and also likes goofy comedies, but at the end of the day that information isn’t going to make us weak in the knees when we are around them.  I’ve equated the whole endeavor to a crap shoot.  Sometimes you get lucky after the first roll of the dice, but most of the times you are both out of luck.  So fear not if your date seems bored and you just want to go home 15 minutes into it.  It’s not you, it’s not necessarily your date, it’s just random luck.  So gentlemen of online dating – please see these dates for what they are – two strangers just trying their luck at a seemingly impossible task. This isn’t college and you aren’t the cute boy in Biology class, but it’s OK.  We can’t go back to that simpler time in our lives, we just have to keep rolling the dice and hope that we eventually hit the jackpot.

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Dating Online: Advice for Men – How to completely mess up the First Date

English: stamp with the words "Fail"...

English: stamp with the words “Fail” and “attention to detail” (Photo credit: Wikipedia)

I’ve written about this before in my article What Men should NOT to do on a First or Second Date, but I decided I needed a shorthand version – a cheat sheet if you will.  Also ladies, consider this shorthand for extremely negative behavior.  If some guy is doing several of the things on this list…RUN!!!!!   I’m making this specific to online dating because I think it’s a fairly unique way to meet people, and fraught with peril.  If you totally want to sabotage a date early, here are a few sure-fire ways to do it:

Say any one or more of the following phrases:

  • My bitch, crazy, psycho, ex-wife or ex-girlfriend – I get it, you had a bad breakup.  This is not the time for a festival of bitching.
  • I’m still in love with my ex-wife or ex-girlfriend – This has happened to me more than once…no joke.
  • I have to pay way too much child support – Well maybe you think you do, but would you rather have your kids live in a box on the street?
  • How many guys have you slept with? – Are you kidding me?

The following will make you look like a liar, even if that wasn’t your intention. 

  • I lied about my age on my dating profile
  • Oh by the way, I have a girlfriend – This information should have been on your profile
  • Oh by the way, I have kids – This information should have been on your profile
  • Oh by the way, I’m married – This happens more than you would think…and of course…this should have been on your profile

How to look rude

  • Make frequent text messages
  • Receive phone calls or make calls
  • Constantly check your phone in front of your date
  • Never ask your date any questions about herself, just give her a non-stop biography
  • Take your date to an expensive restaurant and then ask her to split the bill – If you are on a budget do coffee or drinks
  • Insult your date – You would be surprised how often this happens
  • Discuss politics or religion – Unless of course you know 100% it’s OK to go there, it’s not exactly romantic
  • Show up late or cancel at the last-minute – things happen but if some catastrophe occurs, contact your date immediately and BEG for forgiveness.

How to freak out your date

  • Assume it’s time to start making out, when your date has given you no indication that it’s cool do go there
  • Drink to the point that you’re a drunken sloppy mess
  • Assume your date does drugs, and then tell her it’s a deal breaker if she doesn’t
  • Force your date into a social situation with a ton of people she doesn’t know
  • Have an emotional breakdown and then treat your date like a therapist
  • Focus the conversation on sex, and ask intimate sexual questions right off the bat – The only exception to this is if you both agreed ahead of time it’s a casual sex type of encounter, or you met your date on a hook-up site.
  • Get angry when it’s obvious your date doesn’t want to have sex with you – Even if you met her on a hook-up site or with the expectation that you would have sex.  You might have freaked her out, she might have changed her mind.  No always means no, so chill out and let it go.
  • Send your date a dick pic – Although I love making fun of these in my act, dick pics are rude, goofy, and way too forward.  Your date could cancel completely, scream at you or threaten to call the police.  The only exception is if your date has asked to see your business…otherwise DO NOT DO THIS!

My personal #1 Pet Peeves

  • I’ve always thought I was funny, I bet I could do stand-up.  Could you help me get started in comedy? – If you want to get started in comedy then go to an open mic or take an improv or stand-up class…and never ask me that question again.  🙂
  • Get competitive with me about comedy.  Insist your are funnier or try to one-up me with jokes – Unless you really are a comedian…please just stop…no really just stop
  • Never laugh once during the date
  • Demand I tell you jokes, or want to see my act, right there out of context, while on a date – I basically hate you now.
  • Proclaim that you can’t stand cats – When then say that I know 100% that it isn’t going to work out.

Dating in NYC: What Men should NOT do on a first or second date.

Texting on a qwerty keypad phone

Image via Wikipedia

I am adding the following disclaimer to all of my dating related blog posts.  I change details, and create composite characters when I write about dating archetypes such as “Mr. Houdini, Mr. Angry, etc.  I would hate it if someone wrote about a high energy blonde comedian negatively in a blog, so because of that I never include a person’s occupation or anything about their physical description.  I also change enough details that I doubt anyone I am referring to would even recognize themselves if they read one of my articles.   I have split one person into three, or taken several people and put them all into one example.  So simply put, I am very ethical on this blog.

A happily married friend suggested that I should write this list because as he put it.

Some men just have no clue

And because I get a lot of men on this blog searching for all sorts of knowledge about dating, I thought I would give it a shot.  So based on my experience and an extremely unscientific poll of feedback from my female friends, ranging in age from early 20’s to late 50’s I came up with this list.  Many of these are obvious and universal as they apply to both genders.  And mind you I am far from the “perfect” dater.  I make every mistake known to man…and then some.  But in the interest of the public good….here we go.

These tips apply to when you are actually on a date with a woman…not before.  Online dating tips are another thing entirely.

Tip #1 – Don’t forget to compliment the woman on her appearance.  You don’t have to say much but you had better believe that whomever agreed to go out with you or meet you for a drink has spent a great deal of time on their wardrobe, hair and makeup.  Even the less is more type of gal is going to want to impress, so a simple, “You look nice” or “You look lovely” will do.  It is always a huge mistake to say nothing, especially on date number one or two when you barely know the woman. When a man says nothing to me, I assume he is not that interested.

Tip #2 – Don’t look cheap – You don’t have to spend a lot of cash, it can be as little as a drink.  Under no circumstances go dutch.  It is just rude, especially on the first date and especially if you were the one asking her out.  You don’t need to buy an elaborate meal, and you don’t need to spend a small fortune.  But at least OFFER, she may decline but it is a nice gesture.   Even if you think that in 2012 you shouldn’t have to do this,  it is simple common courtesy to offer something even just a cup of coffee or a glass of wine.

Tip #3 – Don’t bitch about ex-girlfriends or ex-wives – I am extremely guilty of this one – just don’t do it!  It is best to keep things light.  You might mention the divorce or breakup, but then do not bash your ex or go on and on about her.  It just makes a woman feel completely ignored, and as if she is some type of free therapist…BAD FORM.  When men have done this to me, I might feel sorry for them, but I don’t take them seriously as a potential partner.

Tip #4Don’t complain about money, that you have no money, or that you are broke…even if you are broke.  Again, you need not be a Rockafeller to impress your date.  I know of countless lower income men who do quite well with the ladies.  When you bitch about your finances you might make the woman uncomfortable, or feel obligated to somehow take care of you.   It is a lot of pressure and totally inappropriate.  You can bring this up later, but when you first meet someone, it’s generally a bad idea.

Tip #5 – Don’t start talking about sex too soon – Now this one is true in most cases unless you met this woman on a hook-up site or for the express purposes of just having sex with her.  In most cases you will just freak out your date and she will want nothing to do with you. If she brings the topic up first, then its different.  Never assume however, that sex talk will lead to sex.

Tip #6 – Don’t text or talk on the phone in front of your date – If it is a work related or family matter, get to quickly and get back to the date right away.  It’s best to physically walk to the bathroom, or to another area when you do it, then apologize profusely and get back to you date.  Don’t make a habit of it, and don’t constantly check your email or text messages in front of your date.

Tip #7 – Don’t go on a bitch fest – So many times I have sat down at a table with a perfect stranger and they just go off on some rant about their landlord, their job, their neighbors or any number of things.  It makes a horrible first impression and it is best avoided.

Tip #8 – Don’t go down a laundry list of questions – Sure everyone loves to talk about themselves but you can make a person feel interrogated when you simply throw one question right after another.  A date is not a job interview relax, talk about something light like the weather.  Also wait for her answer.  I can’t tell you how many dates I have gone on where a man asks me a question, only to cut me off before I answered it.

Tip #9 – Avoid lightening rod topics – Again obvious, but you would be surprised what I have heard from friends: abortion, politics, rape, religion, avoid anything that might alienate you from your new potential partner.  It is one thing if you already have a good idea of the person’s religious or political beliefs from an online dating profile or if you know you have similar beliefs.  But this is not time to preach or convert, if you never want to see the woman again, then this is a sure-fire way to make that happen.   And don’t ask your date if she wants children on a first date – you are putting her on the spot and it is WAY too early to worry about that yet.

Tip #10 – Don’t ask about her former boyfriends or how many sexual partners she has had – This one is just plain rude.  A general rule of thumb is if you wouldn’t feel comfortable answering something don’t ask another person.  And although men might like to brag about how high their number of partners might be, women are usually the opposite.  There are always exceptions to this rule however as some of my female friends make no bones about having a plethora of partners.

Tip #11 – Don’t take her somewhere where you can’t talk – Movies are terrible as you won’t engage in much conversation, as are many music venues.  Keep it simple, but make sure you get to talk if this person is a relative stranger to you.  You might find that she will like you MORE if you actually talk.  Rather than taking her someplace impressive where you will barely share a few sentences between each other. Again if you are just intending on having a sexual relationship with her and not much more, than go ahead and take her to a loud club.  You might confuse or annoy a woman who is looking for a hook-up if you ask her to go on a traditional date.  She might just want to have sex with you and skip the formalities – but make sure you are both want the same thing, before assuming anything.

Tip #12 – Don’t bring up another woman you want to go out with – Think I am kidding on this one?  It just happened.  A somewhat nervous man trying to forward the conversation openly admitted to correspondence with another woman (one I happened to know) on an online dating website.  She happened to be a comedian.  He said he hadn’t gone out with her yet, but was hoping to eventually meet her because he found her fascinating.  I couldn’t make this one up….NEXT!  I have made the mistake of talking about past men, but never a man I wanted to go out with in the future – that is madness.  It’s also tacky to tell a petite woman how much you have a crush on a celebrity that is tall and curvy, the same goes with going on and on about how hot a tall and slender blonde celebrity is when you are on a date with a shorter curvy gal.  Like it or not she is going to make the assumption that whomever you are describing is what you prefer.  DON’T COMPARE YOUR DATE WITH ANOTHER WOMAN.   After you have been dating a while this kind of talk is fine. But when you are just getting to know someone just don’t go there, unless of course you are describing some celebrity your date happens to resemble then it’s not so bad.  I’m a taller than average athletic blonde, when some guy goes on and on about a curvy brunette who is 5’2″, my heart sinks.

Tip #13 – Don’t force her into a socially awkward situation – Don’t also try to meet up with friends, and then force your date to hang out with them.   Your date is essentially a total stranger to you, shoving her into a social situation with a new person, or a bunch of new people is just going to make her more anxious.  When you make the date, and force your date into meeting more new people because it is convenient for you, you are essentially telling your date that she is not that important.  It is a bad call, rude and it shows you have no game.  A first date is not the time for multitasking, if you blow it, you probably won’t get a second chance.  If you would rather see your out-of-town friends, then don’t plan the date on the same night, or end the date and then go hang out with your old friends.

Tip #14 – Don’t openly criticize your date – Look these situations are strange for everyone, for you and your date.  It might take a minute for you both to calm down and really start talking.  If you make a judgment on your date, she will most likely shut down immediately and just want to leave.  And no one wants criticism like this, especially from a virtual stranger and when they are vulnerable on a date.  If your date is being overtly rude to you, it might be time to just end the date and go home.   But if you WANT to see this woman again, don’t pick her apart.  This might seem like common sense, but it happens more than people think.   I have heard way too many stories and had my own experiences with this one.  Personal pet peeve – Hey I thought you were a comedian, why aren’t you funnier? – Well maybe because I am not ALWAYS working.  If I here that particular question one more time…

Tip #15 – Never assume you are going to have sex – This should be obvious but I thought I should write it anyway.  A woman is under no obligation to have sex with you, make out with you or even kiss you – even if you have paid for dinner and drinks.  You might think the date is going extremely well, while your date might never want to see you again.  Some women will go along on date out of a sense of politeness, some will send mixed signals, and some will be downright confusing – it’s all part of the game.  I’ve heard stories of women grinding into men on the dance floor, making out in bars, or kissing for hours in cars who will ultimately say no to sex. You only get to have sex with a woman if she agrees to it.  This is true regardless of the amount of time you spend with her, the amount of effort you put into the date, or even if you spend a fortune on the date.  No always means no.  If you just want to hook-up with a woman, you should make your intentions clear early on.  She may not want to go out with you on a traditional date anyway. Some women are perfectly fine with just sex, but communication is key.  Never assume anything without consent!

If anyone has more tips for me I will gladly add them.  🙂