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Dating Disasters

About six years ago, my dad set me up with a lawyer who was a few years older than I. We met for drinks at Martini Ranch (311 W. Chicago Ave.); he paid. Since we were having such a good time, I suggested we grab dinner. I drove us to Kamehachi on Wells Street and valet parked my car. We chatted more over sushi and were hitting it off - especially for a blind date - and, when the bill came, I offered to contribute my portion of the check, as I always do. He didn’t hesitate to accept my money. After dinner, I gave the valet my ticket, and, before my car even arrived, my date said goodbye, jumped in a cab, and zoomed off - leaving me standing solo on the corner at midnight.

When I retold the story, my brother said I shouldn’t have been surprised by my date taking my money: “Why would you have offered it in the first place?” he asked. He had a point. Although both he and my dad thought the guy lacked some manners, we chalked his behavior up to first-date jitters, and I decided to give him another shot. When he asked me out again, we agreed to meet at Fulton Lounge with our respective groups of friends. He was good-looking and smart, so I thought, What the hell? Once we were at the bar, he asked me what I wanted to drink and ordered a cocktail for me from the waitress, but when my drink came, he made no attempt to pay for it. That’s when his friend reached into his own pocket and bought the drink for me. I never spoke to the lawyer again after that night.

It had nothing to do with the money and everything to do with his manners - or lack thereof. As progressive as I am, when it comes to dating, I still believe in chivalry and courtship. Even if that courtship happens over e-mail or IM - which I’m OK with, generally - I think the guy should pursue the girl, at least initially. He should ask her out; he should arrange the date; and he should even open a door once in a while. And, yes, shoot me for saying this, but I think he should pay for the first couple of dates. Call me old-fashioned.

Whether you share my opinion or not, we all have them: dates that make you think someone must be Punk’ing you - because, after all, there’s no possible way he could be showing you his ripped abs at dinner and bragging about how much time he spends working out at the East Bank Club on your very first date. Or what about the doctor who faked getting a page when he realized his date was 15 years younger than he would have liked, leaving within 15 minutes of being seated at NoMi?

As bad as they sound, neither of those scenarios compares to what happened to one particular friend of mine. “My best friend from high school set me up on a double date with a guy who supposedly looked like Michael Jordan,” she recounts. “I was excited to meet this ‘tall, dark, and handsome’ hunk, as she had described him. Yes, he was tall, like Mike, and bald, like Mike, but he was missing a few front teeth and had bad hygiene. She begged me to stay because she liked his friend. Somehow I made it through the night - with the help of a few tequila shots.”

No one ever said dating was easy. For me, maintaining my love life has proven to be a lot more difficult than managing my career. While I’ve never used an online-dating service, a recently-ended long-distance e-affair was better than any in-person relationship I’ve had lately - one of the most exciting flings of my adult life. I’m not the only one who has been wooed electronically, then disappointed.

“Several years ago, I met a guy online,” another friend tells me. “We completely hit it off, and we both thought we were destined to be together. After several months of correspondence via phone and e-mail, he flew in from New York for a long weekend. He was super-attractive, really sweet, and all that I had imagined. The first night of his visit, we met up with a bunch of friends for dinner. We were in the middle of a lively conversation and delicious oysters when - splat - his head hit the table, and he was fast asleep.” Something similar happened again the next night, and when my friend confronted Mr. Narcoleptic about his problem, he was so offended he took off early. She never talked to him again. The bottom line: A perfect 10 on paper (or via e-mail, as it were) does not a perfect man make.

Other dating disasters I’ve heard of lately are of a much creepier variety, like what happened to a friend who uses match.com: “After dinner we went back to his place,” she says. “He showed me his bedroom. I about died when I saw a bookshelf full of Kama Sutra books and a twin-sized bed! He later gave me a coloring book and asked me to color a picture, and then proceeded to show me pictures of himself, [taken] when he used to be a body builder. When he tried to kiss me, I told him I had issues with intimacy and had to go home.”

That’s almost as skin-crawling as this story from my friend who uses jdate.com: “I went out with a guy who spent the entire date telling me how much he loves dirty massages,” she says, horrified. “He went into explicit detail. When we left Matilda, he peed in the alley while I was standing there next to him.”

Talk about not having any manners.

Want to share your own dating disasters? Post them below; consider it free therapy.

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