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As promised in last week’s Dating in NYC Blows post, here are some of my worst dating tales that I suffered through so you don’t have to.

Anything Involving A Boat is a Bad Date

After exchanging numbers with a guy at a party, he sent me a text about a month later asking if I wanted to join him at his company’s summer party cruise. Immediately, alarms go off because I know in my head that a date on a boat is a baaad idea.

Then I get a follow-up text: free food and booze. If I had a dollar for the number of times that sentence has lead to a bad decision…

Mistake #1: Free food & booze should not be the basis of a decision

I met the guy on the boat and, well, it wasn’t the guy I thought it was. I could vaguely place him in my memory as meeting him before, but I really was expecting someone else.

Mistake #2: When spinning plates, use clear labels

That alone really threw me off. If we had met for drinks, I would have still been confused but at least could have a drink and see how things went – leave after a round if it wasn’t going well. But this was completely different.

The guy wasn’t physically my type and didn’t seem interesting enough to be stuck on a boat for hours with. In hopes I could salvage the evening, I talked to some of his coworkers but quickly realized that I just wanted to GTFO. I doubted even booze could solve this problem.

Mistake #3: Booze does not solve all problems

Unsure if the boat had actually left the dock yet, I excused myself to use the bathroom and ran down to see if I could get off this thing. I’ve never had to completely ditch a date before and I felt a little terrible doing it but I really just wanted out.

The crew had just removed the ladder from the dock when a crew member saw me walking over and asked what was wrong. I replied, “I’m really not feeling well. I thought I would be okay on the boat but I already feel sick. Have we left the dock yet?”

They were just about to depart but the crew member said he would go talk to the captain about my situation. A few seconds later he runs over and said the captain okay’d letting me off the boat.

They put the ladder back out just for me! I had never been so relieved to be back on land.

I did text the fellow saying that I was already feeling motion sickness and was going home. I’m not always a terrible person, really.

Don’t Act DTF if You’re Not

There is a lot of potential for a date to go horribly wrong and get unsafe quickly. I’d like to say don’t be an idiot, but sometimes it happens.

After being out late in the city, I took the earliest NJT train back to the middle of NJ where I was living at the time. The train left ny about 5a and everyone is definitely incapacitated in one way or another, including myself. Needless to say, I was happy that a very attractive guy sat next to me.

Shortly after, we were making out.

Mistake #1: This

At some point, he suggested him coming back to my place since my stop was before his. I said that wasn’t a good idea. He asked why not. I said no. We kept making out. He kept saying he wanted to come over, I kept saying he couldn’t come over. He kept asking why. We kept making out. etc etc.

Mistake #2: This

So, we get to my stop and he gets off the train with me. I went from having fun to being pissed instantly and used a firm voice to say he was not coming home with me.

Keep in mind we’re literally in the middle of nowhere NJ at 6a Sunday morning. No one is around this train station.

As we walk off the platform I became more adamant that I was going home alone. He began ranting, “Well now I don’t know where I am and another train won’t be here for at least an hour.” But none of that mattered because I was getting really angry.

At the end of the platform we needed to split directions – I was heading to a very empty parking lot to get my car and the station building was in the opposite direction. I was very worried he would follow me to my car.

Before the end of the platform, I laid down the law in a very assertive voice I don’t get to use often. I think it took him by surprise and he did not follow me to my car. I made it home safely and have now learned that making out with strangers at 6a is the worst idea.

Don’t act down to fuck if you’re not. However, people are allowed to change their mind. So if you end up stranded in the middle of New Jersey, it’s your own damn fault.

Pay Attention To Words

I had met this guy several times before through a common-interest group and enjoyed talking to him well enough to go out with him. The first date was going okay but there wasn’t the connection I thought there was and I grew bored. I was ready to call it when he brought up a place near-by that had some special beer and asked if I wanted to check it out. Always curious, I decided to go.

Mistake #1: Thinking the date will get better

Well. If I had been paying closer attention I would have realized that he wasn’t talking about another bar but about his apartment! I didn’t realize this until it was too late. I probably could have bailed at his building door but, for whatever reason, I went along with it.

Mistake #2: This

Awkwardness ensued as it was clear he wanted to get laid and I just wanted to go home. After a little bit, I turned him down and ran out of there.

He emailed me several times after that but I wasn’t interested. A month after our date I received the email below:

laying all cards out:

not too long ago you were interested in getting together. now you only answer emails half the time at best, and just give one-line brush-off responses at that. the only thing that changed is i apparently misread flirting for interest one night. so let’s clear the air:

you’re very flirty and have on more than one occasion made reference to enjoying casual sex. and while i enjoyed just talking to you, of course i asked you out to dinner and back to my apt with this on my mind. then i got shot down. big deal. well, for some, it seems.

since we both know “busy” is bullshit, here are the top two reasons i can think of for avoiding me (though they aren’t mutually exclusive):

1) you suddenly find me really annoying, obnoxious, etc., and would just as soon undo my existence in your life were it possible;
2) you’re worried that i’m in love with you and would make hanging out with you painful and awkward.

i didn’t feel it was necessary to tell you, but if the main reason you don’t want to talk to me is #2, it might help if you knew you weren’t the first girl i kissed in may, nor were you the last. i’m not, nor ever was, “stuck” on you. i’m only telling you because one time you seemed like you were a cool person to know, and if that was the reason you changed then it might assuage any concerns you have and help you reclaim lost coolness.

now that i’m done, that felt better to say than i ever imagined it would! so now that that’s off my chest, i’ll give you a chance to respond if you like. (knowing what a nonresponse means, too.) so long,

I never responded.

When you’re newly single, dating is fun! Let’s go out! Have a drink! I get to dress up! This is fun! Everyone is neat and interesting and cute! Sex! Yay!

This quickly turns into dreading a date because you know it is going to be a dud and you’d rather sit at home watching cat videos on youtube than listen to another person blab on about whatever who cares. But we all suffer through in hopes that we will someday be able to post our own engagement photos on Facebook.

I have gone out on a lot of dates in nyc. All types of dates. Dates with guys, dates with girls, dates with couples, dates in hope of a relationship, dates in hope of sex, dates from ok cupid, dates from parties, dates that were good, dates that were boring, dates that were terrible.

Numbers Game

It seems like dating in a giant city would be easier than a smaller one. There are many more types of people to choose from. It is much easier to find someone who shares your interests. If you have a very specific niche or kink, it’s likely that someone else who shares your passion also lives here.

What this really mans is: more jerks, more assholes, more narcissistic creeps. Sure, it also means more good people, more nice folks, more successful people. But in the end, you need to get through a lot of jerks to find the good ones.

Demographic-wise, there are considerably more single females than single males in all of nyc. There’s even a map of nyc singles by neighborhood. Queens and North Brooklyn are dominated by single dudes, while Manhattan and the rest of Brooklyn are mainly single ladies. If this is bumming you out, move to LA.

Money Isn’t Taboo

Either you have a lot of money or you don’t, but either way it’s rather acceptable to discuss this in new york on a first date. Openly discussing rent prices isn’t as taboo here as it is in other places. While you still wouldn’t reveal your actual salary, knowing someone’s monthly rent can provide a good enough approximation anyway.

There have been numerous dates where we both wanted to go to a happy hour or a specific bar because of it’s weeknight-specials. Talking about favorite cheap eats and ridiculous rent prices is frequent conversation here.

Use the Subway to GTFO

Using public transportation instead of driving a car really works well for dating here in the city.

It’s really nice not feeling like you and your date are separate the whole night. While you initially will both enter the bar as individuals, you will go to your next stop (if it gets this far) together – as a quasi-couple. There is something fun about walking together, agreeing on another place together, then walking into a place together. There are zero limitations the way there would be were cars involved. This also allows for more conversation, freedom from staring at someone across the table, and may bring up impromptu topics which can help dates feel less repetitive.

For good or bad, without worrying about driving home you can drink more alcohol. Sometimes you’ll regret this, sometimes you won’t.

Even if you don’t necessarily live near each other, sometimes you will both take the same subway home. Now, if the date isn’t going well, lie about this somehow. Or stay out. But if things are going well, this ride home can be a nice little extension. It has a set-end and you are both in a place you’re comfortable.

Not having a car makes leaving and staying much easier. You can leave a date any time you want. No matter where you are, you will most likely be near a subway and that will get you home. You don’t have to wait for dinner to be over if you don’t want to. You don’t have to wait to be driven home. You can just up and go.

With that said, you can also very easily go home with someone else.

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Avoid Competition at All Costs

Do not play actual games on a first date. No board games. No card games. No miniature golf. Nothing.

I learned this the hard way. On the OK Cupid profile, one of the things she was “really good at” was Scrabble. So, I thought a good opening message would be to challenge her to a game. Playing board games in bars is very common here and I thought it would make for a fun evening.

As the date started, we had a drink, chatted, and seemed to hit it off. She actually looked like her profile photo, which isn’t as common as it should be.

After a little bit we bring out Scrabble. The problem with a game, like a movie, is you don’t have a chance to actually talk. Also, it prominently displays someone’s strengths/weaknesses, which honestly you don’t want to see on a first date.

During the game she briefly discussed how competitive her and her family were. That was a bad sign. I am not competitive at all.

Also unfortunate, I was winning and she was getting frustrated. It did cross my mind to throw the game and let the pretty girl win. But my pride wouldn’t let me do that.

She played off the loss well but it was clear she wasn’t pleased and that set the tone for the rest of the time. After we finished that round of drinks we both ended the night and neither one of us contacted each other.

Although the idea of “doing something” is a good one, just save this type of stuff for a second date.

The Dreaded Profile Photo

When I was not looking for a relationship, I had several dates with couples to have something fun/casual/no-commitment. This is a minefield. If you think it’s hard enough to find one person you like & find attractive, try finding two of those people together!

Most of these were duds, not good or bad, just not going to work out. One, however, was the first time I finally was able to sympathize with guys’ complaints about misleading profile photos.

Thankfully, guys don’t lie about their looks when it comes to online dating. If they’re overweight, not that attractive, or unemployed, most will just lay it all out on the table. This is greatly appreciated because it saves a lot of effort later.

Unfortunately, girls are not nearly as upfront about the things they don’t like about themselves. Whether the photo is a “msypace angel” (nsfw) or from 10 years ago, these tricks seem so predominant in online dating.

As expected, the guy looked like his photo. Stubble, a little chubby, but Brooklyn cute. Now, the girl had clearly used an older photo and the resemblance was slim. That got awkward real fast and we all quickly agreed that it probably wouldn’t work.

Don’t Bring Your Friends on a First Date

During my time of recreational dating, I was trying to figure out what I wanted and didn’t want to close out any options. One of my dates was with a 42-year old guy. I was mentally fine with this although I know I physically look closer to 25 than 30.

He invited me to an art gallery opening for our first (only) date. Things were going okay… then some of his friends showed up. The two friends were a guy and girl (not together) and were about his age. Apparently they had all planned on meeting up at this art opening but he never told them he was bringing a date. That was weird.

It quickly became clear that the woman did not like me one bit. Numerous times during conversation, she prefaced her stories with, “that was before your time”, “you probably don’t remember this”, “you’ve never heard of that person”. Everything she said was extremely condescending toward me.

My date never said anything to her, maybe he didn’t notice it, but it really was incredibly rude.

I couldn’t figure out if she liked my date or was simply jealous because I was younger. Once I realized the two friends were never leaving I just left and went home. No loss there.

Don’t Criticize Your Date

It’s amazing how often this happens. I really question people’s understanding of what is appropriate to say to others. I’ve had dates criticize that I ordered a sandwich for dinner, that I ordered a beer, that I was too dressed up, that I wasn’t dressed up enough, that I picked a bar they didn’t like, that one of my hobbies is ‘stupid’.

Now, before the Game Theory people get all up in arms and tell me that this is just light-hearted negging, I’m going to tell you you’re wrong. Do that shit in the flirtation stage at a bar or during the early message conversation, not on a first date. At the very least learn the difference between teasing and insulting.

Bonus Tip: When having a threesome, do not criticize your significant other by comparing them to the third (this happened).

Get Your Ex Issues Sorted Out Beforehand

It’s probably just me but I have had several dates call things off on the 2nd/3rd date because they were “probably still in love” with their ex.

First, if we have only had 1,2,3 dates, you don’t need to make a big production out of not wanting to see each other again. I’m not in love with you. I probably barely even like you. Do whatever you want with your ex but don’t waste my entire evening over it.

Second, get your issues sorted out before you start dating. I do understand that sometimes trying to move on brings out new feelings you might not have noticed otherwise. But seriously, get over your ex, pull your shit together, then start bringing new people into your fucked up life.

A Wedding/Company Party/Vacation is Not A Good First Date

I was asked to be someone’s wedding date as our first date.
I was invited to someone’s company holiday party as our first date.
I was invited on a day-trip out of the city as a first date.

None of these things are good ideas.

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Have Sex ASAP

I understand all the arguments for/against waiting a few dates before sleeping with the person.

Yes, sex complicates things and gets folks to continue a dying relationship when they shouldn’t. However, sex is really important! It can tell you a lot about a person and you do want to make sure you’re sexually compatible before investing too much energy into a person.

I have only had one situation where, after sleeping with a guy on the second date, he later said we had sex too soon. Too bad. It was super-great sex and I have no regrets.

Dating just for sex is easy but going to a bar is much easier. From an episode of This American Life:

Anyone in New York City can have sex any night of the week if they just follow two rules, which is stay at the bar until 4:00 in the morning and dramatically lower your standards.

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Small Successes

Yes, I’m still single (hello there attractive readers!) but not every date I’ve had has been the worst-thing-in-the-world. Here are a few places I have had luck with.

Craigslist: Surprisingly I was able to find a couple that I consistently & casually hung out with via Craigslist. However, I don’t generally recommend CL for dating and couldn’t imagine using it while looking for a more-serious relationship. For niche things, it does it’s job.

Reddit: Go ahead and lol all you want but myself and some others have met good people via reddit meetups. There is a subreddit too, r/r4r, but it feels a bit like Craigslist. However, I met one girl that way and although things didn’t work out romantically, we’re still good friends.

OK Cupid: I have a distressing love/hate relationship with this site. Most of the dates from here are complete duds because OKC’s “algorithm” is just made-up numbers. But sometimes things work out. I have had two good dates that actually went somewhere from the site. You’re probably thinking to yourself, “two? that’s nothing.”

Trust me, in the world of dating, two successes means you’re doing pretty darn well.

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Big Fails

I have certainly had my share of idiot-moments in the world of dating. Including discovering the smallest penis in existence, secretly escaping off a boat, and receiving a 5-paragraph post-first-date email.

But these embarrassing stories deserve their own post. Look for that next week!

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Single folks, what are your thoughts on dating? Rules? Good dates? Bad dates?
People in relationships, how did you pay your dues before finding the one you love?