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

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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.  🙂

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