This happened quite a while ago but something recently reminded me of it.
I was set up on a date with a friend of a friend. We'd exchanged a few emails and seemed to enjoy a similar turn of phrase. I picked her up at her place, and the descent into lunacy began.
A few miles down the road we were at a light and this car pulls up next to us, some relatively ordinary car that had clearly been suped (sp?) up because it was louder than hell and the guy kept revving it as though inviting me to a race I would ultimately decline. My date says, "I think fast cars are really sexy." I laughed, thinking she was being facetious. She was not, and she was now angry at me for laughing at her not with her. I tried to apologize and explain my laughter was meant in support of what I thought her position was, but she was not mollified. Oops.
We headed to Quincy Market in Boston, I'd never been. As we approached an older woman approaches selling flowers. I very politely declined. We looked around, and in the course of wandering see several other similarly attired older ladies at some distance selling flowers. We ended up heading a few blocks away to get some dinner. A few minutes into dinner she pauses, looks directly at me indicating she was about to say something significant, and says to me, "I thought you were a jerk for not buying a flower from that woman. Don't you care about old people?" Ouch. I was pretty stunned. I remember some weak attempts to provide sudden proof that I did care about old people, and people in general, and that that incident really didn't seem like a fair way to judge my character. The conversation limped along and eventually the check came. She now announced her brand new philosophy, which I was apparently the first to experience... She said, "I've been treated really badly by guys in the past, so from now on I'm requiring that anyone I date pay for all our dates." Wow. I don't mind paying for others, I'm a bit of a communist when it comes to mealtimes, from each according to his means, to each according to his needs. I'll pay for friends, coworkers, dates, pets, whatever. Different people often offer at different times, and I figure it all evens out in the end (monetarily or karmic-ly). And I would have gladly paid for her portion out of kindness, need, chivalry, simplicity, whatever. I usually make the attempt and if someone stops me (as usually happens) then we figure it out from there. But the notion that I was being required to make up the debt (in cash) created by her previous poor choices in men hardly seemed a fair or inviting situation. I kindly explained that I didn't mind paying tonight, but in general I really couldn't go along with the idea that I who had never wronged her was somehow supposed to compensate for those who had. She took in the argument and seemed to see it had some merit.
At this point I was pretty well tired, it just seemed we were very poorly matched despite some initial clever email banter and mutual admiration of stories we'd each written. We began the 15 minute walk back to the car, and I mentioned a camping trip I was going on. She spent the next 10 minutes telling me far too much information about how she can't go camping because there can be swarms of bugs and the bugs remind her of all these bad LSD trips she's had as well as reminding her of the horrible withdrawal symptoms she's experienced detoxing from heroin. I, who have never done any drugs, let along hard core ones, was really ready for the night to be over. While I am certainly sympathetic to her discomfort with swarms of bugs and all they mean to her, it was just way too soon and too contextless to be sharing that sort of information. (I've dated people who've used drugs, seems like most people have used or tried them, and it's not been a problem, but that's probably because they didn't insist I know so much graphic detail about their experiences, and certainly not on date one.)
The date ended a few minutes later, but not before she explained to me that she was obsessed (literally) with Mel Gibson, that her recovery from the drugs involved watching all of Mel Gibson's movies over and over again and that now she was in a very real way obsessed with him, because he was there for her when no one else was. She said the walls of her room were covered in Mel Gibson posters, she watched at least parts his movies every day, and that if she ever met him she would have sex with him, even if she was already in a relationship, that the other person (I felt implied) would just have to deal with that absolute and unarguable reality.
I dropped her off at her place, we had a little hug (no kiss), and I went on my way with no small amount of relief. I felt quite comfortable that the date was as awful for me as it was for her, since I couldn't relate to and didn't resemble much of what she wanted or liked. Being a nice guy and not fond of ambiguity, I planned to write her the next day and very politely make it clear that I enjoyed her friendship and would be happy to see where that went while acknowledging that dating was really not in our best interests.
Before I had a chance, however, I was shown just how wrong my perception of events had apparently been... she wrote me the next morning to let me know how great a time she had had and how much she looked forward to another date. Ugh.
It took me quite a few hours to come up with just the right way to thank her while politely declining additional dating. She seemed to take it well. We did hang out a couple of times as friends before she found distraction in someone with a far larger engine than mine.
She was actually quite a nice girl, the original connection we had was simply not viable for anything more than friendship, and on that level it worked quite well (however briefly). She was not quite so intense as a friend, seemed less intent on requiring me to be anything other than who I was. Still, doesn't change the fact that it was the worst first date I ever had.