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You almost kind of expect to have some bad dates in your twenties. I’ve had my share: Still Living at Home Guy, Always on His Cell Phone Guy, Just Not Ready for a Relationship Guy, and most frightening of all: Disney-Obsessed Guy. But because the dating pool seems to shrink significantly as we age, I think there is something especially horrific about a bad date after age 30. I thought I had a more finely tuned loser-radar by this point, but this one slipped by me.

I met him at a coworker’s wedding. We were the only two singles at a table where all the happily marrieds were comparing job promotions and baby photos. He had piercing blue eyes and a wicked smile. It was “like at first sight.” We chatted all night, and then he walked me to my car. I was impressed by the fact that he acted like a gentleman and didn’t try to maul me in the parking lot the way I’ve had other men do. We exchanged numbers and made plans for dinner later that week.

During the week he called every night, and we spoke for hours about life, love, and the perils of dating after 30. He was self-employed, owned his own home, and generally seemed to have a good head on his shoulders. I like guys who are really smart and funny, and this guy was both. As Date Night drew nearer, I realized that I was actually excited about a first date for the first time in a long time.

He picked me up right on time, and we drove to a local seafood restaurant. As we approached the entrance, he patted his pockets and looked back toward the car. “Oh, crap, I forgot my wallet,” he said. It was 7 p.m., and I was starving, so I said, “It’s no problem — I can pay.”

He was shocked and went on and on about how it just wasn’t right for a girl to pay on a first date. He wanted to drive 20 miles back to his house to get his wallet. I told him, “Look, you can pay me back or send me flowers or whatever makes you feel better, but, seriously, let’s eat.”

He finally relented but began pouting. He just wouldn’t let it go. I rarely drink, but at that point I seriously considered ordering shots for both of us. He ordered an iced tea, so, okay, no alcohol. When he began acting out his sour mood with rudeness toward the restaurant staff, I knew that there would be no second date.

After the meal I just wanted to go home; Mr. Pouty-Pants had other plans. He said he wanted to go somewhere else to chat. I was about to say, “It’s late, and I should be getting home,” but when I looked at my watch I saw it was only 8:30 p.m. It didn’t seem as if it was going to be easy to get him to take me home, so I asked where he wanted to go. He replied, “You decide, after all, you’re paying.” Ah, those shots are looking even better right now.

I selected an Irish pub across the street. If I had to stay on this date, I was going to need a drink. At the pub he finally loosened up. We talked, and maybe it had something to do with the Jose Cuervo, but he started to seem more like the guy I had met and liked at the wedding. I thought, okay, maybe he behaved badly at the restaurant because he felt so bad about forgetting his wallet. I started to warm up to him again.

He drove me back to my house and asked to use the bathroom before heading back out. I took the opportunity to grab a breath mint and freshen up a little. I walked him back to his car — and he got in without so much as a glance.

Hello? Are you kidding me? I was a good sport about paying for dinner. I was witty and entertaining. And I was making myself available! I couldn’t help myself — I blurted out, “I don’t even get a goodnight kiss?” I should have known better. He got out of the car and came at me with his tongue hanging out like a Saint Bernard. I still gag when I think about that kiss.

What happened the next day? Thank goodness, absolutely nothing. No flowers, no phone call, no emails, no texts. I never had to deal with him again. I did hear later through a mutual friend that he was so embarrassed about the way the date had gone that he couldn’t bring himself to talk to me again.

Tell us the story of your breakup and/or date from hell and we will publish it and pay you ($100 for 500-2000 words).

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bluenwhitegokart Sept. 27, 2008 @ 3:03 p.m.

You got off light. Consider yourself lucky.


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