First Date Do NOTs: Learning From Others’ Mistakes

In light of Valentine’s Day approaching and all the first dates that will be occurring, I was planning on writing an article on what not to do on a first date. Then I thought maybe it would be better to learn from others’ mistakes, so I decided to ask around for some of my friends’ funniest or most awkward first date stories. Enjoy the laughs, and of course, always avoid being the subject of a story like one of these.


I took a girl on a date and during dinner I kept getting texts. I kept replying to them to which she made clear she thought was rude. Then, more than halfway through the dinner I was like, “Listen, I’m really sorry about this… I wasn’t expecting it at all… but my ex-girlfriend was driving and saw my car in the parking lot and is outside wanting me to come out to see her.” My ex made a huge deal, actually called my date nasty names, and was successful in making it the most awkward first date of my life.

So, I took a girl to the movies and almost everything was sold out except for “My Bloody Valentine”. I hadn’t seen the previews on commercials so I figured, how bad could it be? It’s a Valentines movie. Well, it turned out to be the goriest, bloodiest movie ever. It was in 3d and within the first five minutes somebody gets a pickax to the back of the head and the person’s eyeball is on the other end of it. The girl was so scared- the movie was like torture for her. She wasn’t interested in going on another date.

I asked a girl that I really liked to go to dinner with me, and she agreed. I was really stoked and planned it all out. It was a rare rainy night in California. I picked her up and we were on the freeway heading to the restaurant when I realize the car is losing power. In all my excitement and planning, I didn’t check one of the most important things… how much gas was left in the car! So I pull over to the side of the freeway, I have her stay in the car so she wouldn’t get wet, and I walk like a mile to the closest gas station in the rain to buy some gas. When I get back and I’m putting the gas in the car, a lot of it spills and gets all over my jeans. So aside from me being soaking wet and the reservations I had made being canceled, I also reeked of gasoline.

I took a girl out to dinner and then we were “lingering” in my car at a park near her house. Then her brother called asking where she was and she told him at the park. Ten minutes later her dad caught us and was knocking on my window. She jumped out and I drove off as fast as I could. So, a few weeks later I took her and her friend to the mall. She didn’t even tell me her friend was coming though. Rude. So we went and this time I was just not into her at all. So I went into a store on my own, and ran into a girl from work and just started hanging with her. Next thing I knew, I was leaving to go to a party with her… without giving the others a ride home. I felt horrible when I was leaving but I never got a call or text asking where I was, so I guess it was fine.


I actually just went on a date with this dude to a sushi restaurant and he only took me there because I love sushi- he had never tried it. We got a bunch of different things, and he had no idea what wasabi was. He put a huge glob of it on his chop sticks and ate it. He was trying SO hard to play it off but you could tell he was dying and could see the sweat dripping off his head. He proceeded to just say that it was “the atmosphere making him hot”. That was a particularly bad excuse considering it was snowing outside.

I went on a date with a guy who I went to school with. The next day he told me I owed him for my half of the meal.

I was on a date with a guy I met at a bar and we sat down for dinner. I left my phone on the side of the table. He left both of his there too. Yes, he had two cell phones. I asked what the extra one was for, and with the most serious face I’ve ever seen, he just said, “Business. That’s all you need to know.” I didn’t ask again.

I went on a first date with someone to a Mexican restaurant. He spent most of the time telling me about his tattoos. He had a big Yankee logo on his calf, with drawn on skin tears to make it look like it was under his skin. The artist had drawn in lines and blood to make it look like the logo was coming out of his skin. He also had some eagles on his shoulder. The biggest surprise though was a big lifelike portrait of his mother’s face on his chest. I remember wondering if I would fall in love with him, and what would happen if we slept together. Would it be like a Mona Lisa thing, with the eyes following you?

A cute guy was sitting at a booth in the mall and we made eye contact, so I went over to chat. We got along really well and he asked me to dinner that night. We exchanged phone numbers and I left. He picked me up later, and the whole ride I was thinking he was so funny and cute. Then we got out of the car, which was the first time I ever saw the guy standing. He was literally the shortest guy I’ve ever seen. I’m 5’3’’ and I towered over him. Then at dinner he told me all about his best friend in jail who brought a knife to a club. I definitely never dated a random guy from the mall again.

If you’re still reading, the following may be the greatest first date story I’ve ever heard…

I met a guy online. He said he was 23. I was 20. I waited for him at a French restaurant thinking we were going to have French food. I hadn’t eaten all day and was starving. I got to the restaurant and he wasn’t there, so I went to the bar and drank wine. He showed up 30 minutes later and the first thing he said to me was, “You have beautiful porcelain skin. You and I would make beautiful children.” When I asked him what his favorite thing on the menu was, he said he had already eaten. He then said we were going to a lounge. On the way, he shoved me against a wall and kissed me, which was basically attacking me with his mouth. When I pushed him off he said “You’re really lucky to be out with a guy as good looking as me.” So we get to this lounge and he shoves me into a wall again and kisses me, then looks at this other chick that is watching us and goes, “That’s my ex.” He had brought me there just to make her jealous! I tell him I want to leave and he follows me to my car and gets in. He lived like 2 blocks away and actually expected a ride home. He wouldn’t get out of my car so finally when I got to his apartment he’s like, “How about coffee in central park tomorrow?” I yelled “Get out of my car!!” Finally he gets out and then he calls me and goes, “I think that went really well.” He then invited me to his 35th birthday party the next week!! Meanwhile, I still haven’t eaten.

Anyone else have an interesting first date story?

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3 Responses to “First Date Do NOTs: Learning From Others’ Mistakes”

  1. Richard Hertz of Holden, MA Reply Feb 03, 2011 at 9:36 am

    Never EVER have a first date at a strip club.

  2. These stories were awesome! Thanks for the laughs!

  3. Never date a fellow law student.