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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6 comments on “Top 10 Rules for Dating in New York City

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