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  I remember that feeling in the air at my first fraternity date party in college, when all the guys were scrambling at the last minute to figure out whom to ask and what to wear. I still get that feeling every time I go on a date or buy a girl a bottle of wine. Life to me has never ceased to be like one big game of childhood dress-up. Taking a girl to dinner is just about the most mature thing I’ve ever done. When I’m in the middle of a date I can’t help but think I’m still eighteen and soon everyone is going to expose me as a fraud.

  The logistics of dating also pose an enormous obstacle for someone as neurotic as myself. If I’m going out to dinner in Los Angeles, my first issue is parking. I can find the restaurant OK, but once I get there I can’t park and end up driving in radiating concentric circles until I find a spot a mile away from my initial destination. The girl probably thinks she’s in the midst of a kidnapping attempt and I’m trying to disorient her. And parallel parking, forget about it. When I first moved to LA, I was driving an SUV for the first time in my life. I was always scared and unsure about how much space I needed. I swear I parked like a gangly adolescent girl self-conscious about her developing new body.

  I cringe when I go to a restaurant for the first time and the waiter asks if I’ve eaten there before. Because I know that if I answer truthfully, I’ll then be subjected to a ten-minute instructional lecture on the intricate aspects of ordering tapas. Listen, if your menu is so complicated that living on earth for thirty years doesn’t give me sufficient knowledge to order from it properly, I’m probably not going to like any of this weird-ass food anyway.

  When the check comes, there should be absolutely no debate: I’m paying. Ladies, any guy who doesn’t pay for you is fucking worthless. Any guy who offers to split the check should hand in his man badge and have his testicles confiscated at the door: he’s done. If we make it a few more dates, personally I appreciate when the girl does the fake, reach-for-her-purse move. I’m still paying, but I respect the fact that she’s playing along. A few more dates and, yes, I will let the girl pay. But only if she insists. I know I’ve been spending a shitload of money on her the past few weeks. I also know she’s spent a shitload of money on clothes, makeup, waxing, manicures, and other crap I can’t even consciously perceive, but all of which collectively made me want to go out with her in the first place.

  THE SET-UP

  In the twelve years I’ve been writing my Ruminations column, I’ve received a staggering number of emails—from soldiers overseas thanking me for giving them a laugh to a fan who quoted me while proposing to his girlfriend (apparently he was a hopeless romantic, emphasis on hopeless). But I’m always surprised when I receive emails from mothers and fathers trying to set me up with their daughters, and chicks trying to set me up with their girl friends. Apparently, everyone is fair game for being set up these days. It’s also interesting how every mother describes her daughter as “gorgeous.” Somehow that seems unlikely.

  I almost always regret allowing my friends to set me up. Because I’ve found that friends who know you best are the worst at setting you up. Perfect strangers are much better at it because they don’t overthink things. For instance, my tastes are very clear: I prefer brunettes, I like girls in wife-beaters, and I’ve got a thing for doctors. But that does not mean you can only set me up with brown-haired surgeons wearing beaters. If the chick is just hot, she’ll do. I’ll bang a blonde. Let’s not get picky.

  A woman will tell you everything about one of her friends, but leave out the most important part: “You have to meet my friend, she’s gorgeous, you’ll love her.” I respond, “Is she single? No? Then who the fuck cares?” Ladies, lead with that information! What do I want to meet a chick with a boyfriend for? What, are me and her gonna become friends? Read Us Weekly and eat nonfat frozen yogurt and share lip gloss and go shopping for candles and ballet flats? Don’t introduce me to chicks with boyfriends. You might as well introduce me directly to the boyfriend. The net result is the same: no pussy for me.

  * * *

  OBSERVATION

  How long a girl stresses the word “so” when describing how cute her friend is is inversely proportional to how cute her friend actually is. For instance, if a girl is like, “You have to meet my friend Ashley; she’s soooooo cute!” that chick is busted.

  * * *

  My guy friends don’t get very creative when they’re thinking of girls to set me up with. Once my frat buddy Scott asked me, “Karo, you want me to introduce you to this chick Susan? She’s pretty hot.” “I guess,” I said. “How do you know her?” And Scott was like, “I fucked her.” That’s not really thinking outside the box. But the thing is, that didn’t even deter me. I contemplated it for a moment and then asked, “Well, how long ago did you fuck her?”

  MATCHMAKER

  My single female friends always want me to set them up but it’s so annoying. My friend Jen recently asked me to set her up with a buddy of mine she thought was cute. I said, “Sure. I’ll just shoot him an email, I’ll talk you up, and then I’ll have him friend you on Facebook.” Jen responded, “Oh, I don’t have Facebook.” And I said, “Well, I’m not setting you up then.” When she asked why, I asked how the hell my guy friend was supposed to stalk her first if she doesn’t have Facebook. Before my buddy would agree to ask her out, he needed to see several pictures of her from multiple angles and at least one photo album from Halloween to see how slutty she dressed. That’s the basic starter package.

  Then I tried to set up my friend Deb. I was on the phone with her as she was looking at pictures of her prospective suitor when she asked, “Does your friend have blue-green eyes?” I was stunned for a moment then exclaimed, “I don’t fucking know what color eyes my friends have! I don’t know what color eyes my mom has! I don’t know what color eyes I have!” When the line went silent, I said, “OK, I mean, do you have a thing for a specific eye color? I guess that’s reasonable.” Deb responded, “No, but my psychic said that I would meet a guy with blue-green eyes.” Seriously? Did your psychic also predict that I would call you a fucking moron?

  * * *

  ZODIAC FILLER

  I can’t believe there are women out there who still read their horoscopes. “He’s a Leo and I’m a Sagittarius. It’s perfect!” No guy has ever fucked a chick he met at a bar and then thought to himself, “Well, I guess our moons were aligned.”

  * * *

  Most guys know at least one girl that they only keep in touch with because she has a lot of hot friends. There’s nothing more disappointing than when I call up my go-to gold mine and her friends can’t hang out, but she can. But what frustrates me most is when a girl tells me that her cute friends are single but “not looking.” Single but not looking? What the fuck is that? “Well, you know,” she says, “if the right guy came along…” Every chick’s “not looking” until the “right guy” comes along! So basically what you’re saying is I’m not the right guy. Fair enough.

  When one of my guy friends gets set up with a chick who is supposedly very attractive and went to Penn or is from Long Island, and he calls me to ask if I know her, I’m always really chagrined if I don’t. If a dude is looking to me for confirmation and I can’t provide it, I’m the one who looks bad. Guys are supposed to have radar lock on every hot girl with a given background or within a twenty-mile radius. I’ll never admit I don’t know her, so I’m just vague and evasive. I’ll make shit up like, “Uh, yeah, she sounds familiar. I think my friend banged her once.” Then of course he asks me how long ago my friend banged her.

  REAL WOMEN THROW CURVES

  As someone who is naturally prone to observation, I find the study of women to be a particularly frustrating endeavor. The more I know about them, the less I understand. Nothing defines the difference between men and women more than our relationships with members of the same sex. A woman moved in across the hall from a girl friend of mine and she confessed to me, “I hate my new neighbor; she’s so thin and cute.” Imagine if a guy moved in next door to me,
and I was like, “I totally hate my new neighbor; his hair is so straight and perfect!”

  Why do women get upset when you’re hooking up and don’t notice their “new pretty bra and underwear”? Yes, I know we’ve been dating for several months, but I still couldn’t pick your thongs out of a lingerie lineup. I’ve been trained since puberty to consider bras and panties mere speed bumps on the road to glory. They are to be smote as quickly as possible without regard to make or model.

  * * *

  OUT OF THE MOUTHS OF BABES

  While it’s surprised even me that most of the stereotypes about people in Los Angeles aren’t true, you would still not believe some of the statements I’ve heard from chicks in this fair city.

  From a girl in my apartment building whom I overheard telling her friend about a new all-liquid diet: “Yeah, it’s pretty good, but you kind of miss the chewing.”

  From a chick I hooked up with, when I asked her if she liked LA: “Well, sometimes I just want to go away for a year to someplace warm.” (It was eighty-one degrees in November at the time.)

  And, possibly my all-time favorite, from a girl I was walking with in the Hollywood Hills, through a beautiful but heavily wooded area: “Oh my God! This totally reminds me of Rainforest Cafe!”

  * * *

  I once met a girl at a party who clearly had fake breasts. Later, my friend told me that she was a virgin. This annoyed me. Virgins shouldn’t have fake breasts. In fact, if you have implants before intercourse, I think you should get an asterisk on your V-card.

  I also don’t trust a woman with the number 2000 in her email address. If she chose it after the millennium, it demonstrates a lack of creativity. If she chose it before the millennium, well, she really wasn’t looking too far ahead. Chicks should also never, ever use text or IM abbreviations in real life. Newsflash: LOL and OMG are not real words. Say them out loud again and I’ll TTYL.

  WHAT A GUY WANTS

  Guys typically have unreasonable expectations. It’s not unusual, when asked if a girl is attractive, for a guy to tell his friend, “She’s cute, but if she lost, say, thirty-five pounds, she’d be slammin’.” In our heads, we actually believe that this is both a reasonable request and an easily attainable goal. On the other hand, guys will steadfastly refuse to change anything—our weight, our hair, or our underwear—to satisfy a chick’s slightest preference. Our appearance is nonnegotiable, no matter what the consequences.

  We can also be unapologetic dicks. I was in a bar once when I saw a girl I knew back in the day but hadn’t seen in a while. I said to a mutual friend, “Hey, is that Leslie? She looks amazing.” And my buddy said, “Yeah, she was actually sick for a while. She had really bad mono; like she almost died.” I said, “Damn, that’s the best thing that ever happened to her!”

  * * *

  ODE TO A WIFE-BEATER

  What do I look for in a girl? Is it a sense of humor? A certain body type? Shared interests? No. I’m really just looking for someone in a wife-beater. I think chicks in beaters are incredibly sexy. That’s my thing. Now, just to be clear, a wife-beater is white. If you’re wearing anything but white, or anything with rhinestones or designs of any kind, that’s not a beater, it’s a fucking tank top. I’m talking about the kind of beaters you get at Target in a pack of three for $9.99. A beater is not just an article of clothing, it’s a statement. A chick in a wife-beater is saying, “I don’t care what you think.” She’s saying, “I don’t need fancy clothes to look hot.” But most of all she’s saying, “Hey you, stranger, look at my tits.”

  * * *

  I love how some women actually think they look cuter in glasses. Um, no. The whole time, all I’m doing is imagining what it would be like to fuck you without your glasses. Some girls wear glasses even if they don’t need them. What, do I have a librarian fetish? And to the chicks who do need a prescription: quit being so goddamn lazy. If I can have lasers burn fucking holes in my eyes, you can throw in some contacts in the morning.

  Ultimately, what guys absolutely do not want is drama. For instance, I kinda wanna bang the chick who cuts my hair. But I’m forced to balance that notion with the possible fallout. Afterward, would I ever be able to get my hair cut there again? Does she seem like the clingy type? Those scissors do look sharp. The last thing I want to do is risk upsetting her and leave our next appointment with a mohawk or, worse, one less ear than I came in with.

  IT AIN’T EASY DATING ME

  I would be lying if I said that the lack of success I’ve had with romantic relationships was due solely to the irrational behavior of the women I’ve dated. I’m acutely self-aware and can admit that getting along with me is no piece of cake. I can be neurotic and downright strange. For instance, I sometimes Google misspelled words to find web sites with poor proofreaders. When using a new bathroom, I often search for the little indent where the doorknob keeps hitting the same spot on the wall. I’m not really a lover or a fighter. I fret, worry, observe, write, and repeat. In essence, when it comes to relationships, it’s not that I’m high maintenance, per se; it’s more like there’s no instruction manual and they stopped making the parts.

  Another wonderful trait I have is noticing little things about people—a certain word they use, an idiosyncrasy or flaw they possess—and then calling it to their attention, thus making them incredibly self-conscious. Then I profusely apologize for doing it. Finally, after the issue has long since been forgotten, I get drunk and bring it up again, thus aggravating old wounds. After apologizing yet again, I usually make another comment about the person’s clothes, career, or hygiene, and the pattern continues.

  * * *

  NEAT FREAK

  Some might say I’m a tad obsessive-compulsive. When I was a little kid I went to this museum that had a piece of, like, four-thousand-year-old glass that you could touch. People were amazed at feeling something that our ancestors had created so long ago. But all I remember thinking about is how many other people had touched it since.

  * * *

  My cell phone number happens to be comprised of multiple variations of the numbers six and nine. When I give my number to chicks, they look at me like I’m a dirty bastard. Some guys get a bad reputation from sleeping around. I got mine from T-Mobile.

  The people tanning at the pool in my apartment complex in LA always look like they’re in such anguish. Is that supposed to be relaxing? Perhaps I’m just jealous because I’ve recently come to terms with the fact that I am the palest motherfucker in the state of California. The problem is, being in the sun doesn’t help because I just go from white to burnt without any browning in between. I seem to carry the recessive gene for tanning but the dominant gene for beer belly.

  ACT YOUR AGE

  During my five-year college reunion in 2006, I snuck into my old fraternity house, which at the time was being used as some sort of community service dorm. As I wandered about taking pictures, a student approached and asked politely, “Excuse me, who are you?” Instinctively, I turned around and yelled menacingly, “Who the fuck are you?” The girl scurried off, but the incident made me wonder if or when I’m ever going to act my age. Consider this: I’m thirty years old, with three books under my belt, regular car insurance payments, and pillowcases that match my comforter. Yet at the same time, I can’t drink one beer without drinking twenty, I can’t converse with a girl without trying to fuck her, and I can’t even step foot in a fraternity house without immediately regressing into an asshole. Am I young at heart or just immature?

  The last time I was in Miami, I crashed with my college friends, Jon and Jana, who are now married. We went out and got stupid drunk. I then proceeded to vomit all over their guest bedroom and, when that room proved no longer inhabitable, passed out in the living room on their white leather couch, staining a pillow with the stamp from the bar on my hand. But the worst part was that Jon and Jana didn’t really get mad at me. They understood I didn’t do it on purpose and I did my best to clean everything up. That really bothered me. The fact
that they weren’t upset made me feel like their rascally little kid who is always caught up in some hijinks. They should be pissed at me. Hell, I’m older than they are!

  * * *

  PARTY FOULS

  I was at a party once and pulled an Amstel Light out of the fridge. Two of my friends whipped bottle openers out of their pockets. And not sophisticated bottle openers, mind you. I’m talking about the big, round keychain kind with half the paint chipped off and a college logo on it. I was taken aback. Though they’re handy, isn’t there a cutoff for carrying bottle openers? Junior year, perhaps?

  * * *

  I recently found out that my buddy Jesse has a female roommate. And like most guys, my first question was, “So, do you tap that? Is there some sort of schedule? How does it work?” Of course, they don’t hook up. But then I met her for the first time a few days later, and not only is she cute, she’s got Civil War cannons. Now, I’m not positive about many things in life. But I am absolutely sure that I’m not mature enough to have a female roommate. Because I would harass the shit out of her. I would come home drunk, bang on her bedroom door, accuse her of leaving her dishes in the sink, offer to let it slide if she blew me, and then wonder aloud what possible downside there could be to roommates with benefits. Then I’d realize she wasn’t even in her room and, when confronted by her once she actually did get home, have to admit that I urinated on her door because I thought it was the bathroom. And that would be the first night.