I once had a date with a guy who constantly bragged about his sailboat and how amazing he was at sailing.

I Started asking questions about said boat and he didn’t know what a jib was or even what kind of sailboat it was.

Bonus, after repeatedly bragging about how much money he had, asked for a separate check. Which, splitting a bill is fine, but to do it after specifically bragging about how rich you are?

Not “disastrous”, but I don’t drink, and she was deep into home brewing.

I’d tell you, but it’s been so long I can’t remember

Never dated

So I presume Cory is single now? Send him my way. He’s my type.

I never had a real disaster of a date, but one time on a first date, we went to this place near the ocean with a short walk down to a little beach with a really nice view. Across the path was a chain hanging about a foot off the ground. I thought I’d be dashing, so I mocked it and said something like “Silly chain, you can stop me!” and then proceeded to try and jump over it, and instead catch my foot on it and face plant.

We were together for three years before circumstances forced us amicably apart.

This comment section needs more tldrs

Fairly tame but also recentish… I was very clearly a strawman for her ex. Now, I know that sometimes when my sense of humor doesn’t mess with someone else, it’s grating. That’s fine but I know this about me, and I was honestly dialing it way back. An amusing anecdote here, a witty quip there. History shows this vanilla formula works and is well received by both potential romantic partners and coworkers alike.

But she was just uggggggghhhh. “Why are guys like this, I’m trying to make a real connection and you are telling jokes?!”

My sister in Zeus, I don’t even know what color your butthole is and you are already on stage 4 of decoupling. How. If you want to work through the crazy in the bedroom I am so fucking down but I haven’t even gotten through my second drink yet.

The best part is that we are neighbors. It was one of the first matches I had in my new place and she was like six doors down. So I still see her in passing fairly frequently and we like awkwardly wave or nod or sometimes pretend not to notice each other. Somehow I feel like there’s another chapter to write, and I would absolutely still go nine innings with her if she wanted (and my wife was cool with it) but I have never played therapy date like that before.

I was snowboarding and staying at a hostel on the mountain. A man with a broken ankle who walked with the aid of a staff, we called him Moses, gave me a bag of shrooms, which I ate. A tinder date responded, so I went to meet her, but she was staying in a very fancy resort lodge which was a 20 minute hike up the mountain. Upon getting there she introduced me to her family. I remind you, this is a tinder date first meeting. There was music and dancing and quite suddenly I was far too high to exist in normal spacetime, so I said in a grave voice “I have to go now” and just left. The 20 minute walk back to the hostel in the cold and dark snow was the longest 90 minutes of my life, I had never been as high on mushrooms as I was that dark august night. I genuinely believed that if I fell in the snow I would not be able to get up. Eventually I made it back to the hostel where I was sharing a room with 3 very drunk Russians I’d just met, and I promptly did a week’s worth of shits in 15 minutes in the adjoining bathroom, and spent the rest of the night clinging to the bunk bed and trying to to fall off the Earth.

We met at a workshop and collab’d on a project. I asked if she wanted to go have a coffee with me some time. She said yes but didn’t seem too happy about it. At the actual date she just looked disdainful. Getting answers out of her was like wringing blood out of a rock. At the end I just decided to leave it, and left on as friendly terms as I could.

I still don’t know why she agreed to come. I hope she didn’t feel like she had to? I’ll never know

I had a first date where the guy thought it would be a great idea to take me to a park and serenade me while strumming his ukelele. I am certain that floats other people’s boats, but I am not the type of human that ever wants that kind of intense one-sided attention, especially in public. I gave him a second date because I felt horrible about how awkward I was about the whole thing, but the second date made it clear he just wanted a woman to marry quickly and have children. Which is also not a thing I’m into haha.

I screen people a lot more carefully now, so both sides don’t end up terribly disappointed

Still a better love story than twilight

Not a date so much as a “hookup”. We hung out for a bit, went to my place, and hung out on the bed for a while. Eventually we started making out, and things escalated. I got literally two strokes in when she told me to stop. Okay, fair enough, consent is always revocable, it’s fine.

So we’re back to sitting in the bed and talking, and ten minutes later she’s back on top of me, kissing even more passionately than before. Escalation again, I confirm that she wants me to put it in, and three strokes later she tells me to stop again. Okay, consent is still revocable but this is getting ridiculous.

We go through this cycle two or three more times, each time confirming consent, each time only getting a couple thrusts in before she tells me to stop. That combined with the vast swings between doting and negging just rubbed me the wrong way. She was so hot-and-cold that I felt like she was fucking with me on purpose.

I did not call her back.

I’m really conflicted because I am in this meme and I want to be able to laugh at myself, but also, I just got broken up with & it feels too soon

I think this was more funny because I don’t always read the room very well.

So we’re on a date, and she says “hahah I’m not wearing socks” and I didn’t think much of it. Then well we dated for a couple years and I learned what she tried to imply. She was a feety girl. Somehow I didn’t connect the dots until a couple years later of dating. She said things like, I’ll make my feet pretty for you. And I just thought, ok you do you.