Ask a Pro

Dear Head Pro,

So throughout college and high school I dated pros, bros, and the like. But after a breakup with a major WASPy pro I'm over it… kind of. Recently I've met the opposite of a pro. He's a crass, chain smoking immigrant with trashy tattoos who couldn't afford college so he went into the Army and is now waiting tables to pay for med school. Weirdly, I'm falling for him big time. He's cute, smart, funny, and thinks I'm beautiful (so he has good taste at least), but he hasn't asked me out because he knows I'm too good for him and knows I know I'm too good for him. Oh and he's five years older than me. I feel like I'm in a less fab version of Aladdin without the magic carpet and pet tiger. I don't know if I should go for it or wait for someone better? Our life experiences have been so different and I'm not even sure if it would work out, but I can't stop thinking about him. Plus my last relationship ended almost eight months ago and I haven't liked anyone as much since. So should I pass on the 99%, or give him a chance?

Hesitant betch

Dear Hesitant Betch,

Fear not, because there comes a time in every bro/betch’s life where we find ourselves mesmerized with the great unwashed, at least briefly. In Vegas, one of my bros was so convinced that the stripper we paid to give him a lap dance was in love with him that he actually tried to find her when her shift was over. A girl I knew in college who typically dated bros with family money is now engaged to a dentist. I know, right? They’re not even real doctors! For those of us who count ourselves among (or at least aspire to) the 1%, a little sexual charity never hurt anyone. I feel like there’s probably even a way to write it off on your taxes, but I don’t know because I don’t hate myself and hence am not an accountant. So like, what’s the standard federal deduction for fucking a girl with an H1-B Visa?

Though atypical for a betch, dating a guy with higher than average mileage can pay dividends. A guy who’s older than you and has seen rougher times can make for the pro-est of pros once someone gives him a shower and a haircut. His life experience will make him a lot more interesting than some foppish ponce named “Truxton” who never had to work a day in his life, and having to grind his way through life should make him a lot more appreciative of what little he does have. Besides, it’s not like you’re contemplating fucking Miguel the dishwasher. This guy’s an army veteran and is in medical school. If you can snag him now when he doesn’t have income to justify a full-on pro swagger, it might be worth it in the near future.

So by all means, allow him to occupy your own personal Wall St (with his boner). Sure, he might feel a little out of place at a wine tasting (particularly when he finds out your dad owns the winery), but that will pass. If it doesn’t work out, fuck it. Just don’t eat at that restaurant anymore.

I thought Aladdin had a pet monkey?


Head Pro

Dear Head Pro,

Do you believe in some kind of unrequited love thing? I haven't been dating this one asian for like 2 years but can't get him out of my head. Last summer he told me he still loved me but then I was like, nah. We would fight a lot because we were really similar so that's why I broke it off. It's been a long time and I've gone a lot of places and met a lot of people and have still not found someone with whom I could have what the asian and I once did. What does it all mean?!


Dear Ambiguous,

This is probably my favorite email that I’ve ever received (it should be noted that the subject line was “garbanzo bean”), and a perfect example of why you should never email me while under the influence. Or crazy, or whatever is going on here. What does it all mean, indeed.

Not that this email isn’t stupid (because it is), but it touches on a broader theme that I see a lot in emails: this idea of “searching” for the perfect guy. A lot of girls seem obsessed with the idea of having some kind of fairytale romance, and/or are terrified of not having a boyfriend at all times. The simple fact is that if you base your self-worth on your relationship status, no one is going to want to be with you. Men find desperation and insecurity just as repulsive as girls do. It’s like if instead of carrying on with my life, I instead spent my free time moping about how I’ll never be Batman. I mean, that does make me pretty sad every time I think about it, but life goes on.

If you can’t find someone with whom you can have what you had with your Asian bro, it’s probably because you view every guy you meet through the lense of what you had with your Asian bro. Approaching any interaction with the pretense of a relationship is a really terrible idea and puts a lot of pressure on someone you barely know. Relationships just happen; you can’t act as though you’re auditioning a group of hopefuls until you find the “right” one. Making a sex tape? Then yes, you should absolutely audition people. It’s amazing to me how bad some people look in the glow of a night-vision camera, particularly when they weren’t aware of said camera. Always do your due diligence.

Unrequited kisses,

Head Pro


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