Submitted by Kate, Age 29, Boston

It had been a LONG time for me since I’d last been with a guy and certain body parts were going to go on strike if I didn’t get some action soon. Enter Charlie. I met him at the gym (which was probably my big mistake right there, but anyway…). He had kind of a young Val Kilmer thing going on and he was a lawyer and smelled real nice (even at the gym), so, yeah, I was VERY excited when he asked me out.

We met at a French restaurant and he arrived looking and smelling even better than normal. We sit down and we’d barely started reading the menu when he lays this one on me:

“You should know, if I act at all funny tonight, this is my first date since my girlfriend broke up with me. It was a pretty emotional breakup.”

Uh, okay…

“No problem,” I say, ignoring the warning bells in my head.

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Submitted by Frustrated Online Dater, Age 27, New York

Attention Online daters… here are some things to avoid:

(6) Telling your potential date that your interests include going out sometimes and staying in sometimes. Surprising, I know, as this does make you sound very unique and very exciting. But more information is required.

(5) Having a profile in which you sound bitter and angry with the world. Once again, shocking that this is not a turn on, I know. Also bad, putting up a photo of you scowling… you would be surprised by how many people actually do this angry, “I am really pissed off” photo thing.

(4) Putting up photos of you and a child who is not yours, but forgetting to write, “not my child”… this can throw a potential suitor off just a little.

(3) Continuing to instant message someone who has turned you down multiple times. By the tenth time that you are rejected, you really should figure out that s/he is not about to change her/his mind. I recently returned to the online scene, and this one man continues to just keep on trying, hoping I’ll have a change of heart. But I haven’t.

(2) Emailing your potential date photos of your highly unattractive genitalia. Yes, some man really did this to me thinking it would work. He emailed me asking if I was impressed. Impressed by how unattractive and horribly pale and pimpled he was? Yes.

(1) Having a photo of you in a wedding dress on your profile with the screen name “AreYouTheOne”? Doesn’t work so well. Who knew?

I had just moved out of my old apartment, but due to some poor planning, my roommate and I weren’t able to get a subletter and ended up paying rent on two places for a month. My wallet still hates me. My roommate had already moved across country, but I was still in the same city, so I planned a party on the final Saturday of our old lease. Since my former landlords were douches (for lack of a term which means more-douchey-than-douches), and since I didn’t have to pay a deposit on that place, I had no qualms inviting over 300 people, supplying a ton of booze, hiring a DJ, and throwing it down in the most down-throwingest style I could. When life hands you lemons, you throw a fucking party and serve the lemons with Jose Cuervo!

A few days before the party, I footed it over to the local pub to down a hard cider (what? I like cider!) and watch a little baseball. The regular drunken clientele were there, but there was also a new woman who appeared to be friendly with the bartender (always good), so I started up the chit-chat with her.

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“If you’re on the pill then we don’t need a condom. Trust me, I know when I’m getting an outbreak, and I’ve been totally clear for over a month now. It’s all good.”

Submitted by “It is SO not all good”, Age 23, Minneapolis, MN

Valentine’s Day was probably not the best night for a first date, but we were both single and I figured it might make a good story if things actually worked out. We met at a restaurant, though I didn’t learn until we met up that she didn’t have a car and conned a friend of hers into driving her over to the restaurant at the last minute. Things started off on a decidedly low point when she asked me right off the bat if my parents were divorced because she was also looking to set up her mother, and wouldn’t it be fun for us to go out on a double-date: me and my dad with her and her mom. (My parents just celebrated their 35th wedding anniversary this past August.)

Over dinner, she began to tell me about her prior boyfriends, most of whom had been abusive in various ways. I also heard of her parents’ messy divorce, her father’s alcoholism, her repressed memories that are starting to surface (some of which involved more abuse) and about a thousand other details about her life – mostly because I couldn’t get in a word edgewise.

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It was Sunday in Madrid, and I was on a 24-hour layover. It had taken two hours from the airport to the bus to the train to my hostel, which had a McDonald’s on one side, porn shops on the other, and a shower that fell off the wall. I needed a night out.

Manuel, my only friend in Madrid, was away for the weekend, “would be back to hang out, but probably late”, and wasn’t answering his cellphone. I didn’t have a phone of my own, but figured I could call him from anywhere. So I set out, armed with Manuel’s number, my Rough Guide, and enough Spanish to get myself in trouble.

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He wasn’t the best-looking guy, but he was confident and charming in an “I’m a nerdy badass” kind of way. That’s why I went out with him in the first place. He was upbeat and weirdly funny, and by the end of our second date, I was still intrigued—not sold on him yet, but intrigued.

We were walking on the Upper West Side, where we both live, and we ended up outside his place. He feigned surprise. “So, I actually live right … here. Wow, how’d that happen? So you wanna come upstairs?”

See how this can be perceived as kind of charming if one doesn’t know any better?

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I was supposed to meet this girl at 7pm for dinner. I showed up right at 7pm. 7:05 came and went… 7:10… 7:15… Finally, at 7:20, I said to myself, “If she doesn’t show up in 5 minutes, I’m going home. I’m hungry.” Naturally, she showed up at 7:23, begging forgiveness for being late because she had a really good excuse. “I recently stopped taking my antidepressants, and one of the side effects is that it makes me tired,” she said. “And so I slept through my first appointment with my new therapist, and she said that if I couldn’t make the first appointment, we couldn’t have a good working relationship at all so I should find a new therapist, and I was really upset because she was supposed to be really good, so I had to go out and go shopping.”

I should’ve just bailed out there. But you know how in sitcoms when people are just bowled over with information and they can’t process it, so it’s like their brain just kind of skips over it and stores it away to process later? “I’m pregnant!” “Ooookay, what do you want for dinner?” Yeah, like that. I was hungry, so my brain skipped over all that and “oookay, let’s go eat!” came out of my mouth.

Over dinner, I found out the myriad and sordid reasons why she’d been taking antidepressants in the first place. It turns out that (a) her father, who was president of their congregation, was having a public affair with one of his congregants, which in turn made (b) her mother into an alcoholic, which in turn made (c) her sister… well, she really thinks it was more of a cry for help rather than a full-on attempt because she only took half the bottle of aspirin. Yeah.

After dinner, I said my goodbyes and started walking home, and she began walking fast to keep up with me, asking if I was tired and did I want to hang out more — it looked like I lived close by since I was walking home. Yeah, I was tired… of her. I got the distinct impression she was trying to invite herself back to my place for some lovin’, but there would be no joy in Mudville that night.

Submitted by Keith, Age 30, Los Angeles

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