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Let’s Dissect an OKCupid Date Gone Bad

You’ve were given issues, I’ve were given recommendation. This recommendation isn’t sugar-coated—if truth be told, it’s sugar-free, and will also be a little bit sour. Welcome to Difficult Love.

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This week we have a very special edition of Tough Love. We’re going to break down this woman’s not-so-great first date beat by beat.

Keep in mind, I’m not a therapist or any other kind of health professional—just a guy who’s willing to tell it like it is. I simply want to give you the tools you need to enrich your damn lives. If for whatever reason you don’t like my advice, feel free to file a formal complaint here. Now then, let’s get on with it.

Hey Patrick,

I wanted to run a date I had by you. I had been talking to this guy for a couple weeks who I met on OKCupid. We were vibing. Talked on the phone a couple times and texted everyday. So we finally planned a first date at an arcade bar.

For starters, waiting a couple weeks is probably too long of a screening period. I know you want to be cautious and safe, and that’s good, but the sooner you can make some plans for your date the better. Otherwise, you have a lot of time to read too much into each other’s text messages, lose the excitement and energy you felt when you started chatting, and begin to have second thoughts or change your mind. Plus, come the first date, you have nothing to talk about because you’ve already gone through each other’s exhaustive interview process. Either you’re into this person and they make you feel comfortable enough to meet them, or something isn’t right and you should move along.

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That said, an arcade bar is a great first date spot. The games ensure there’s always something for you to do and talk about.

The day of the date he texted and informed me that he would like to take me to Chili’s for apps and drinks before the arcade bar. He also says that he has a gift card that’s going to expire soon and I don’t mind that. I did, however, think that he was going to pay the remainder of the bill. But instead he looked at me after the meal and asked what I ordered. We literally had the same exact thing. We split a triple dipper and both had two margaritas.

It’s pretty normal for both parties to pay for their own things on a first date, especially a semi-blind one from the internet. But he changed your already agreed upon barcade plans and said “take you” to Chili’s, so yeah, he probably should have covered you there. Geez, nothing says “I’ve got my shit together” like using a Chili’s gift card on a first date and not offering to split the remainder. What a gentleman!

Also, I forgot to mention that his car is in the shop so our plan was to Uber together to the next location. But he kept mentioning that he thought I was going to drive and how that would be easier.

Yeah, he doesn’t have a car…

Then, about halfway through our food, he tells me that he’s so exhausted and doesn’t wanna go to the arcade bar and would rather go catch a movie. I would’ve totally gone to the movie theater, but he wanted to come back to my place, and when I said no, he was almost guilting me and talking about how I’m “afraid of the world.” Then he got upset when I told him that I don’t bring home men on the first date because they might be a murderer. I said this in a joking manner, but he took offense to this and said that a statement like that is “character assassination.” I apologized if what I said offended him and everything seemed cool.

This screams “I just want to hookup! Don’t make me try…” This guy sounds like a tool and you couldn’t assassinate his character even if you tried—it’s not there.

He then moved to my side of the booth…

Uh-oh…

…and talked about how tired he was, and started putting his head on my shoulder…

“Come on, let me nut.”

…and that’s when we called it a night and got the check.

Oh, thank god.

So, I ended up paying for the remaining half of the bill and he was supposed to leave the tip. He left a decent tip, but I had a couple of extra dollars that I was going to leave on the table when we left. As I slid out of the booth, the dollars fell onto the floor, and before I could say anything he snagged it up and insisted that they were his. I know I could’ve said something right then but I didn’t.

Why?! That’s your money! Money you shouldn’t have had to spend at Chili’s in the first place, by the way.

Then after we part ways he texted me later that night. He asked if I had told anyone that we were going on a date. Then he asked how I was gonna describe the date to them.

Wow, okay weirdo… Fixate much?

I told him that I’d say that we had pretty good conversation and it was cool. He then said that he didn’t enjoy himself. And I just said “ok take care.” He then insisted that he was joking and got mad that I was so quick to say goodbye. Then when I explained that I felt more of a friend vibe, he started telling me that I wasted his time and talking shit. I wasn’t going to even mention the money thing, but he kept pushing me. So, I laid out everything that happened that I wasn’t feeling about the date; from him being almost a half hour late (I forgot to mention that) right up to the cash thing. He got so pissed when I mentioned the money. He explained that he really did think it had fallen out of his pocket when he was leaving money for the tip. Which now that I think about it could’ve been true.

This guy is an egotistical hothead. Whether he knew that was your money or not, he treated you poorly and overreacted.

He also pointed the finger at me saying that I could’ve said no to Chili’s, and I could’ve insisted that we go to the arcade bar, and that I should’ve claimed the dollars, and yadda yadda. I am a very self-conscious person, so I want to know how you look at it because at the time I had downed a few drinks and thought that I was totally standing up for myself. But now that I’m sober and thinking about everything he said I feel like I may have overreacted. And if I did, then there’s no taking it back. But how could I try to explain my thought process?

You did not overreact, and you do not owe this guy a damn thing. If anything, you could’ve been more forward when these problems happened during the date. I realize it’s not always easy to be confrontational with a strange man when you’re a woman, but he literally stole your money and you just let it happen. Come on.

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Here’s what probably really happened:

  • You met a guy on OkCupid who you thought was nice based on your chats, texts, and phone calls, but you waited too long to meet him in person so you could find out that he was actually just a broke creep lookin’ to score some easy sex.
  • On the day of your date, he changed plans because he didn’t have any money, save for a Chili’s gift card with just enough to cover his end of dip and margaritas. Or, if he did have any cash, he wasn’t willing to spend it on drinks with you at the barcade you both had already agreed upon.
  • Then, he walked to Chili’s because he doesn’t have a car, and that’s why he was 30 minutes late.
  • After making you wait, he then hoped to get you tipsy enough on margaritas you thought he’d be paying for to fall for his “I’m tired, let’s go to your place and Netflix and chill” routine. “Oh, and you’re driving, by the way.”
  • You didn’t bite, so he tried to guilt you into it. When that didn’t work—because you’re smarter and safer than that—he got angry. So, you had to pay your part of the bill and parted ways, but not before he found a way to steal your money right before your eyes. He knew you wouldn’t say anything and wasn’t going to go home empty-handed.
  • After that, not only did he berate you in his text messages, he managed to make you feel like the one who did something wrong. Do not let this creep fool you.

You did stand up for yourself here, but it was too little too late. You could do more to help yourself in the future. Next time, meet up sooner and see if there’s chemistry right off the bat. You can’t know if someone is only good on paper until you spend some time with them face to face. All that waiting did was give yourself time to invest and set yourself up for disappointment when he turned out to be a jerk. Also, next time, say no to Chili’s, and stick with the original date plan unless there’s a very good reason not to. At least you would have had some fun playing games at the arcade bar. And next time, definitely claim the dollars if they’re yours. Being honest about what’s your property is not going to rock the boat and ruin the mood.


That’s it for this week, but I still have plenty of blunt, honest advice bottled up inside. Tell me, what’s troubling you? Is work getting you down? Are you having problems with a friend or a coworker? Is your love life going through a rough patch? Do you just feel lost in life, like you have no direction? Tell me, and maybe I can help. I probably won’t make you feel all warm and fuzzy inside, but sometimes what you need is some tough love. Ask away in the comments below, or email me at the address you see at the bottom of the page (please include “ADVICE” in the subject line). Or tweet at me with #ToughLove! Additionally, DO NOT EMAIL ME IF YOU DON’T WANT YOUR REQUEST FEATURED. I should not have time to answer everybody only for funsies. ‘Til subsequent time, determine issues out for your self.

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