Submitted by Kayla, Age 28, San Francisco

A couple years ago, I met this guy online. He seemed real funny and gave good e-mail. I was excited for our first date. We met at an Italian restaurant, and he looked gorgeous. So far, so good.

“So how was your day?”

Here’s where he screws it up. He starts telling me about going to the doctor that day for an STD test. Yes, that’s right. He made sure to explain that he was 99.99% sure he was fine. He heard from a friend that a girl he was with three years ago now had gonorrhea, and even though he had no symptoms, even though this girl used to be real innocent when she dated him and subsequently turned into a slut, even though he had no real reason to believe he had an STD, he just wanted to make sure. He tried to make this a humorous anecdote, delivering it in an “aren’t I so edgy and ironic to be talking about STDs on a first date” sort of way. He also seemed to think this story showed how uber-responsible and clean he actually was, that it was a real feather in his cap that he’d just gone for an STD test, even though he didn’t really need to.

Was he a bad guy? No. And I’m sorry if I sound judgmental, but the moment he said the word “gonorrhea,” my vagina closed up shop and the game was over. Guys, just remember, no matter how charming you think you are, there are some things you just don’t mention on a first date.

(It has been some time since my inaugural post, so I thought I’d throw another personal story out there. Do enjoy. — SF)

Submitted by Stewart Fox, Age 28, Los Angeles

I had a big time crush. I was into her and (to a lesser extent) she was into me. So why weren’t we a couple? There were issues. Problems of mismatched geography, mismatched life direction, and that perennial thorn in my side: bad timing. But I had a chance with her. Or so I thought. It was one night only, just the two of us together, not exactly the full-scale long term romance I’d fantasized about, but I knew there was still a chance for something special that night: a chance for one spectacular fling.

First I had to grease the wheels. At dinner, I ordered a bottle of wine. Just the thing to push inhibitions to the point of no return. We both drank. I wanted to encourage her to drink more. So I — very conspicuously — drank more. She sipped responsibly. I sipped frequently. I drank the way people lean to one side during mini golf trying to influence the ball’s trajectory through mental telepathy and body language. I influenced nothing. Except my own good senses.

I began to open up. And it was a gruesome thing to watch. I told her how much I was into her. And then I kept talking. And talking. And telling her things I should have never in a million years told her. And with every word, I could see whatever attraction she once had for me slowly fading away. I’d become this needy guy with feelings, no longer the cool artistic dude she once admired. I was just another guy with a crush that wasn’t going to be returned. I was my own cheap date. And not hers.

Submitted by Trevor, Age 20, New Jersey

I got into an accident on my skateboard and broke the fall with my face. Sucked, but I didn’t think too much of it at the time. Later on, I’m making out with my girlfriend, and my tooth comes out in her mouth. Yeah, that kind of killed the mood. Definitely didn’t get laid that night.

Submitted by Paul, Age 36, Baltimore, MD

I’m in high school. My girlfriend Laura is driving. She parks her Toyota on top of a hill in the middle of the woods. You could call this make-out point except I don’t think anyone else knows about this place except us. At last, we’re alone, two virgins, and the moment is right.

We start making out furiously, and it’s the greatest thing I’ve ever experienced in my 17 years on earth. So hot. So incredibly hot. The parking brake keeps poking me in the side, but I push it down; nothing is getting in between Laura and me now. I climb on top of her, and our limbs intertwine with a passion I’ve only dreamed about up until that point.

… which is probably why neither of us noticed the car slowly rolling backwards. Until …

“Holy shit!”

Suddenly, the Toyota is in the woods and rolling backwards downhill — FAST! God bless, Laura, her foot somehow found the brake before we killed ourselves. But not before the rear of the car had sustained major damage. We came to rest with the back fender hooked around a tree trunk, and we were stuck.

Laura tried starting the car, I got out and pushed, but it was muddy and the car was not going anywhere. For a fleeting moment I thought, “hey we’re stuck, we might as well have the sex we were planning on having anyway,” but one look at Laura’s panic-stricken face and I wisely shelved that plan. The rest of the night only got worse. We had to walk for three miles to find a house where we could call our parents, who then called the police and a tow truck. We gave elaborate explanations for how we happened to be stranded in the woods so suspiciously, so late at night, but it couldn’t have been too hard for anyone to guess what had really happened. We were both grounded for a teenage eternity, forced to pay for repairs, and prevented from seeing each other for so long that it would be more than six months before we finally managed to have sex with each other.

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 Julie, Age 29, Boston, MA

I met Richard in college. We hit it off right away and were good friends from the start, but never more (one of us always seemed to be in a relationship, and frankly, dating him never really crossed my mind). In fact, as he was a pretty shy guy, I occasionally set up dates for him with other girls!

After we graduated, we both moved to New York, where we ended up seeing each other nearly every weekend. One Friday night, I was out with him and a bunch of his friends, and we ended up back at his apartment. We often stayed at each other’s places – we were friends, after all, it was “no big deal,” as I often told my skeptical girlfriends – and, as usual, I ended up crashing on his futon around 2am. Sometime around 3 or 4, I decided, screw being friends, I really liked him, and more importantly, I wanted to get laid. So I crawled into his bed, told him I was “cold” and got under the covers. (Most of us girls have used this line at some point – guys, if a girl gets in your bed and tells you she’s cold, chances are she wants to hook up. If she was actually cold, she would just ask if you could lend her a blanket.)

I don’t remember his exact response, though it had something to do with me being pretty and him being glad I was there. I should point out here that I am a pretty big moron when it comes to guys – I never read the signals right – so, seeing as we were “just friends,” I decided he couldn’t possibly mean anything by it. Despite his shyness, if he was really interested, I thought, he would actually make a move.

Needless to say, he didn’t, and we spent the next 5 hours lying next to each other, wide awake and not touching. We’re still friends, but I’ve never had the opportunity to throw myself at him again, and considering how miserably I failed the first time, I probably never will.

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.

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