Dating In NYC: Learn From My Mistakes

Dating In NYC: Learn From My Mistakes


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.


2 Replies to “Dating In NYC: Learn From My Mistakes”

  1. Well, if I didn’t already know what the common-interest group was, the long explicit letter definitely nailed it.

    And using the “but now I’m inconvenienced!” has got to be the worst way to try to get someone to sleep with you. Hope he fell asleep at the train station and missed the next train, too.

Comments are closed.