Submitted by Allison, Age 23, New York, NY

My first date with “Fred” wasn’t amazing, but it was good enough to warrant a second, and the second was just good enough to warrant a third. I’m pretty picky about guys, and, because I’m aware of how picky I am, I’ll sometimes overcompensate and give a guy a chance even when I secretly know he’s not right. This was the case with Fred. I knew it wasn’t going anywhere, which is sort of why I didn’t put up a huge fight when he insisted on paying for the fancy dinner we ate on date #3.

Throughout dinner, I went back and forth on whether I was going to let Fred get physical with me later. I knew he wanted to pretty badly, and although I knew this couldn’t go much further, he was real pretty, and … did I mention I’m indecisive?

Okay, so he walks me back to my place, and by this point, I’m starting to get tired of his personality and I’m thinking I probably shouldn’t hook up with him. I make my goodbye at the front door kind of hasty, and seeing his chances fly away he makes one last ditch effort: “Do you mind if I use your bathroom quickly?”

Okay. Fine. He gets the invite upstairs. But once he’s done, I pull the “I hate to kick you out but I have to get up real early tomorrow” line, and he’s clearly frustrated. “Oh, man,” he says, “So you’re really kicking me out …” I apologize, but stand firm. He makes no effort to disguise that he’s stewing in his boots now, and he stutters, searching for the right words. Finally he says: “Man! Do you REALIZE how much I spent on dinner?”

I couldn’t believe it. He was trying to make me feel guilty for not hooking up with him, and he actually thought this strategy might change my mind somehow and get me all hot for him. “Um, you can leave now.”

He slammed the door on his way out.

Hey, call me picky, but my instincts are good.

Submitted by Joe, Age 25, Cleveland, OH

Boyz,
If you’re like me and you like big booty, DO NOT mention this to your girl before you get to know her. Dig…

ME: Mmmm, I love me a woman with a big ass.
HER: You did NOT just tell me I had a fat ass!

And this is before things got really ugly. Think twice!

Submitted by Lady of the Lake, Age 20, Ann Arbor, MI

I discovered that my boyfriend had been cheating on me – and he’d done it with two different girls (he’d had sex with one and made out with the other). When I found out, we had a huge fight, and I told him to get out of my apartment and never come back. I was devastated and couldn’t believe I’d been such a sucker.

A couple days later, he calls me and asks when he can come by to pick up his things. I say Tuesday evening. Tuesday comes, and he shows up in this really nice shirt with flowers in his hands. I ask, What’s with the flowers? He says they’re to say he’s sorry. He says he knows we’re broken up and he’s fine with that, but he just wants to apologize. Whatever. He asks for a drink. I refuse. “Just get your shit and go,” I say. But he’s taking his sweet time. Finally, he comes right out and says what’s on his mind.

“You know,” he says, “it’s a shame we never got to have breakup sex.” He pauses and gives me a smile. “Of course, we still could …”

That’s when I spilled my cranberry juice on his stupid fancy shirt.

Submitted by Chris, Age 32, Washington D.C.

I felt confident and mature even though I was barely 22. Fresh out of college, I already had my own apartment, and, after lucking into a plum job at John Hancock, I was making twice as much money as any of my friends. All this, and I had just started dating Sarah, who was not just a knockout, but four years my senior. I was dating an older woman – a hot older woman!

But, as I said, I was young and cocky. And horny. That’s why, after three and a half dates, I invited her to my place for a dinner that I would cook. It had been almost two years since I last had sex, I was eager to close to deal, and I thought, what better way to do it than by cooking her dinner? How mature of me!

The only problem was, I was pretty clueless in the kitchen. I called my mom for help (again, how mature!). We went through all my favorite recipes of hers until we settled on one that was easy and sure to impress: her beef and bean stew.

Did it work? Not exactly. Sarah seemed to like the stew, but she didn’t eat much. Stupidly, I encouraged her to eat more, guilting her, saying, “If you like it, eat more. I’ve made so much!” So she ate more. But then she behaved awkwardly for the rest of the night and excused herself before things could really get physical, claiming a major headache. No sex for me.

Sarah and I ended up dating for two years, and eventually I learned that she had actually wanted to have sex with me that first night, but my choice of entree has scuttled our chances. Sarah has a very sensitive digestive system, and such a healthy portion of beans and beef make her fart like nobody’s business. Apparently, my cooking gave her such a bad case of gas – she’d become self-conscious. She spent the whole evening trying to hide her farts from me, and eventually begged off the sex because she knew she wouldn’t be able to control herself with her legs wide open.

Submitted by Casey, Age 24, Boulder, CO

I’m in college. One date away from finally boning Wanda Lewis, and that date is tonight. I think about her perfect pair bouncing around in those tight tank tops she always wears as we IM to confirm our plans. I’ve been looking forward to this for a long time.

A new window pops up. It’s my boy Evan who wants me to come out to a rager tonight at SAE.

“2nite? u fuckin crazy bro? i’m boning wanda lewis 2nite.”

That ought to make him jealous.

“excuse me?”

Oh yeah, he’s pretending like he doesn’t know her. That asshole. He knows EXACTLY who I’m talking about.

“u know, tank top girl with the tits from murray’s econ class.”

No reply. Then I read:

“casey, are you IM-ing with someone else?”

Holy hell. I’ve been typing in the wrong box.

I am the biggest idiot in the world.

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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“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

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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