After this post was published, I received four emails from readers telling me about their experiences with obnoxious and awkward first dates. Three have given me permission to publish their stories.

Throughout dinner she spent a lot of time talking about her father, who she had only met once when she was fourteen. She was in school for social work and said she was there because of him. At one point she told me something like “so, being totally honest with you, I have major daddy issues.” Then two weird things happened. She took to calling me Pops (my name is Patrick and she tried to act like this nickname was a derivative of that) and after she kissed me goodnight and we spent a few minutes talking (me, really wanting her to get the hell out of my car) she said “I like you. You actually remind me of my dad.” 

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So we get back to his place and he’s undressing me and he says “I never have sex on the first date but for you I’ll make an exception.” So I asked him what makes me so special? and his reply was “all night I’ve been trying to guess if your boobies are real and I want to find out.” It was actually the fact that he said BOOBIES that bothered me. Who the fuck says boobies.

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As soon as I told him I work at the Apple store he goes “If I buy you dinner, will you get me a free iPhone? I want the white one.” I thought he was joking but he asked again. Twice. After I said no, unfortunately I couldn’t do that, he didn’t buy my dinner- even though he was the one who asked me out and chose the restaurant.

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I’ll now open the floor to those who want to write about things said to them during sex which made them never want to see that person again.

I’ll go first.

We had been dating for about a month, both in our early 30s. He was a brilliant and successful engineer and artist. The chemistry between us was very intense and every time we saw each other we would spend hours in bed cuddling, talking, and making out, but had decided to wait to actually fuck. We had so many things in common and we made each other laugh and we had such great deep talks and good fun together that I was actually a bit scared of falling in love with him and also ready for that, in the way you are when you are falling for someone, and we had both discussed being ready to really date and have a relationship.

One night we are going for it, and I’m feeling vulnerable and happy and close to him, and as soon as we start to have sex this is the very first thing he says:

“So, uh… you’re not gonna be one of those crazy weird girls who gets all attached and clingy after we have sex, right? I hate that. I don’t know if this is gonna go anywhere with us and I want you to be okay with that. Cool?”

I realized I actually didn’t know him, at all, not the way he had led me to know him. And I thought it’s called a crush because when it ends, it crushes you. That crush had most definitely ended in such a moment of intimacy and vulnerability, expectation and loss.

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