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You went out tonight and had yet another dismal failure. The best thing that can be said about this date is that at least it was mercifully short, so thankfully she didn't have to put up with you for too long.
It's not that you're a bad dude. You're funny, smart, caring, and (to my male heterosexual eye) not that bad looking of a dude. The problem, roommate, is that you're just a fucking idiot when it comes to dating.
I've had to watch this sad charade for over a year now, and I've had to listen to your sob stories, this constant recounting of how you can't find a nice girl to get into a relationship with. I understand; dating is hard. I'm no magician myself and don't claim to be the all-knowing expert of wooing the opposite sex. I've tried to help you, but you won't listen. Now I'm on Craigslist because I just can't stand it anymore.
Roommate, please pull your head out of your ass. Here are ways you constantly fuck up. Fix these, and maybe, just maybe, you'll meet that nice girl you're looking for.
1. BE ON TIME. You fucking asshole, you are always late. ALWAYS. This isn't a big deal when you're just meeting up with me or your friends for beers at the bar, but it's goddamn rude when it's a girl that you're trying to impress, especially on the first date. The message you are sending is that you were doing something more important than making sure that you were on time for your date. As you get to know her better, maybe this can become one of your cute little "quirks," but being late right off the bat makes you look like a fucking dickhead.
2. IRON YOUR GODDAMN SHIRT! You walk out of the house looking like you just pulled your shirt out of the bottom of the hamper. Come to think of it, maybe you did. But dude, you look like fucking hell leaving with all of those wrinkles. Whether you want to admit it or not, she's going to notice. If you show up looking like crap (and late on top of it, fucko), again you're sending the message that you just don't care that much about trying to make a good impression with her. Take a look at your date--unless you're going out with the neighborhood crack whore, have you noticed that she probably spent more than 5 minutes getting ready? If you want her to look good for you, it's only fair that you look good for her, you inconsiderate bastard.
3. SHAVE. Just fucking shave. Your 2-day growth doesn't make you look like a dashing rogue. It makes you look like a slovenly bastard. Also, I want you to try an experiment: go to the Home Depot down the street. By some #2 sandpaper. Take it out of the box, and grasp it with the palm of your hand, positioning your arm at approximately a 45-degree angle. NOW RUB IT ALL OVER YOUR FUCKING FACE AND SEE HOW MUCH IT HURTS. Doesn't feel too good, does it you stupid son of a bitch? That's exactly what your face feels like to her if, heaven forbid, you actually kiss her. Now, some girls like the feel of an unshaved face. Shit, some girls like to be choked while you fuck them in the ass and pretend that she's an underage ballerina and you're Superman. But that doesn't mean you should show up to your first couple of dates with a gag ball, an industrial-size tube of K-Y, and a goddamn cape. Play the percentages: shave until she tells you otherwise. Asshole.
4. PAY ATTENTION TO THE CONVERSATION. You always complain about uncomfortable silences. Well, dickhead, what is it that you're talking about that leads to silence? You're doing one of two thing: (1) Talking about stuff that's boring as hell to most people, that could lead to potential conflicts, or that makes her feel uneasy (topics in this category include: work, politics, sports, religion and sex). If you get into a relationship, you might have long discussions about any of these topics. That's cool, that's healthy. But whipping that stuff out on the first date is most likely going to be a conversation killer; or, (2) You're talking about yourself. You tend to do that a lot. Shut the fuck up. It's about her, not you. Keep the conversation going by asking her follow-up questions and offering selective tidbits about yourself. That way, she feels like not only are you interested in her, but also she's learning about you. It doesn't matter what questions you ask her, just keep her talking. AND FUCKING LISTEN. Don't go on auto-pilot--she'll pick up on the fact that you're not really listening to her right away.
5. SHOW SOME CHIVALRY. Open doors. Offer to pay for the bill (but don't force it--she might feel more comfortable splitting the bill with you, because then she won't feel like you're "expecting something" as a reward). Be nice to the waitress. Don't look at ANY OTHER WOMEN, no matter how hot they are. As soon as you check out some other girl's ass, you're done. Save that shit for when we're out at the bar getting drunk. Until then, focus on your date. Flatter her. This is something we don't do well in our culture, but find a way to compliment her without coming off like an asshole. Find something you genuinely like about her (her outfit, necklace, shoes, whatever) and tell her. Stay away from the following areas, though: Boobs, lips, legs, ass, and just bascially her body in general. Don't come off as a perv.
6. MANAGE YOUR EXPECTATIONS. Dude, she's not going to fuck you on the first date. It's just not going to happen...and the girl who DOES fuck you on the first date isn't a girl you want to get into a relationship with. If she's fucking you on the first date, how many other guys do you think she's sleeping with? You're not that good looking, charming, or rich. YOUR ENTIRE GOAL FOR THE FIRST DATE IS TO GET A SECOND DATE. That is the only way you should measure success. If you get a kiss after the first date, that's great...but the lack of a kiss doesn't mean shit. And guess what? Your entire goal for the second date is to get the third date. It's ok to ratchet up the physical flirting as the number of your dates increases, but as soon as she feels you trying to sniff out her cooter, you're done unless she already wants to swallow your Special Swimmers.
That's all I've got for right now. I hope you read this. I hope you meet a girl who you can have a good relationship with. I also hope you fucking quit whining about it to me.
Oh, and I need the fucking rent. Asshole.