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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I was dating a guy I probably shouldn’t have, but I was young (22) and I didn’t know any better. He was 30, he made a lot of money, and he was the sort of guy who liked to show you how much money he made, the sort who would aggressively pay for everything just to show you how little money mattered to him. At this stage in my life, I’d be repulsed by that, but at the time I didn’t know any better (or maybe I did but wasn’t listening to the voices in my head)

Did I mention he was hot? Um, yeah. He was kind of hot, which is probably why I let myself get swept up by him instead of running away.

We’d gone out a handful of times, and while we hadn’t technically slept together yet, we’d gotten pretty close. So when he told me he wanted to take me away for Valentine’s, I was pretty darn excited and very ready for the next step.

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Back near the dawn of time, I spent summer and christmas breaks working alongside a smart, beautiful, smart-ass girl. The banter was legendary. Never had I compatibility with someone that devastatingly intelligent, stunning, and, well, dirty. However, due to a high-school-ish lack of self-confidence and cluelessness, I assumed our linguistic sexual interplay was merely in the land of “let’s just be friends”ishness.

Eventually, our friendship progressed into letter-writing and getting together with groups of friends now and then. I think our flirtiness via snail mail and parties got to the point where I somehow indicated my real feelings, for she responded with a “I’d love to go out with you, but [her best friend] has a crush on you and I wouldn’t want to hurt her.” So after much soap opera garbage and letting down the friend easily, I got that first date. And it was spectacular; the specifics were better than I’d imagined (a story for another website?). This was an open-minded girl! But I stopped short of home plate that evening, I don’t know why: I’d never had sex, lack of self-confidence, first date, stupid, etc. And we went on for a couple of weeks, and here’s where the train falls off the track.

Rather than trying to reignite the passion and fun and fearlessness of that first night, I became a supreme fluffhead schmuck. A far-too-expensive necklace for Christmas. Teddy bears. Little gifts all the time “just because.” Discussions at her house, alone, without progressing to making out. Too much obsessive attention WAY too soon. Trying to show her the relationship wasn’t just about sex.

And then, well, it wasn’t. She let me down easy, but she never really explained why she broke it off, to my lifelong frustration. We wrote letters for a while, even with some of the flirty stuff thrown in, halfheartedly, but that was it.

And in twenty years, I’ve never met another woman with that same combination of smarts, beauty, humor, and pure sexuality. How’s that for schmuck?

Submitted by Snake, Age 35, Boston

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

The fairy tale adventure of my romantic life just keeps on playing . . .
A male friend who’s been around for the last year recently broke up with his fiancé. Almost immediately, he turned his attention to me. He made my head turn for about a half a second until suddenly, we were talking, and there was something just lewd about him. All character was stripped and he seemed, eh, I don’t know, not the person I’d known for the last year. I barely recognized him. I called him on it . . .

He told me he was looking for a one night stand to get over his ex and knew I’d “be up for the ride”. I was silenced while he continued – yes, continued! – saying that with my background in theatre, there’s no way I was the “good-girl” I presented myself to be, though “the whole catholic girl routine and clothing” totally works for him (he said this with a wink, naturally).

I probably should have slapped him, but instead, for some unknown reason, I didn’t. Instead, I asked what would make him think that I’d be up for such a proposal. He said, “Oh, I figured shallow and not-too-bright were a good combination for a one night stand. C’mon, it’s just sex. We’ll both have a good time. Let’s go.”

The funny thing is, I liked him before this conversation. Who knows where things may have led had he not been such a prick. Think it, don’t say it. No, try not to even think it.

Submitted by Sarah Clay, London

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