Ask a Pro

Dear Head Pro,

Not usually one to turn to the internet for advice, but I'm about ready to pop a xany over this one.

My boyfriend works at my dad's law office every summer, and this summer one of the young interns whose family we know from the club became disgustingly obsessed with him.  Like she's a total psycho.  She constantly drunk dials and texts him, and will send four or five incoherent texts in a row without him responding.  She's a senior in high school and constantly is calling him crying claiming that she feels unsafe at the parties she's at and needs a ride home (he'll usually call her a cab). She also is a total freak and kept constantly posting pictures of cats on his Facebook until he put her on limited profile. At first it was funny because she is just so desperate, but it's become a huge pain in the ass.  We can't go out to dinner on a friday night without hearing from her at least twice.

Normally, he would just tell her to fuck off, but there's a snag.  My dad has said that she won't be hired back (because she was literally the most incompetent human being on the planet), but because our families share similar interests, he told me that it's important that my boyfriend and I stay on good terms with her. 

I'm used to keeping it classy, obviously, but this girl obviously lacks some social graces . . . and freezing her out is not working.  How can we get this girl to get the picture without looking more “bitchy” than “betchy”? 

You're the best,

Say No to the Ho

Dear Say No to the Ho,

Man, I feel for you. There’s no worse conundrum than having to choose between enduring a crazy bitch’s antics or dealing with her mom muggin’ you at the country club because you offended her poor, innocent flower of a daughter. I guess having to decide whether or not to keep a baby would be worse, but I usually give girls a fake name so I don’t have to deal with that shit. I mean, it’s not my fault you hate America and chose to turn down Obama’s generous offer of free prophylactics.

I think the trick here is for either you or your boyfriend to appeal to your dad’s lawyer-y sensibilities. This bitch is a senior in high school, but she’s going out and getting so wasted that she’s calling your boyfriend in tears. Do you think your dad, a presumably well-respected lawyer, would want your boyfriend (and ipso facto his law firm) doing anything that could even remotely be construed as associating with an underage girl doing illegal things? I think not. Say something like “Dad, I know we’re tight with Gertrude’s (her name, as far as I’m concerned) fam, but she’s getting out of hand. She’s telling us things and asking for our help with situations that could really look bad if it was ever known that we were associating with her.” Trust me, the only thing that rich white people care about more than making money is protecting their reputation.

Continue to freeze her out and ignore her calls. Hopefully your dad will have a word with her dad, maybe over a round of golf or some nice scotch. He’s likely oblivious to his daughter’s out of control behavior and will probably bring the hammer down on her, or at least like take away one of her credit cards. Maybe Christmas will come early this year and he’ll take away her cell phone. Until then, keep up the good work and let the adults handle the family bullshit.

Kitty Kisses,

Head Pro

Dear Head Pro,

A little background: I used to hook up with this bro off and on for about 2 years. We were exclusive for a while but couldn't ever seem to get our shit together so we never dated. You could say we both had feelings for each other (ugh, I know). We drunkenly hooked up a few months ago, but otherwise we don't talk.

Basically, last weekend I hooked up with his roommate… while he was home. The roomie and I have been friends for a while, but it's always been super platonic. Recently things have been a little more flirty between us, but it's whatever. We were drunk and hooked up, but we didn't have sex, so I didn't think it was a huge deal. I snuck out that morning and successfully avoided seeing the bro.

The next night, the bro texted me asking if I had a fun sleepover with his roommate. Apparently, he was awake the whole time and heard us hooking up and was less than pleased. The bro gave me a bunch of shit for hooking up with his roommate while he was home (understandable). He said it was shitty of me to hookup with his friend and that he wouldn't do the same to me because he cares about me, etc. I apologized and he accepted. He then said he didn't care who I hook up with, his roommate included. (But if you don't care, what's the point of bitching me out in the first place?)

Normally I would just laugh it off and move on to the next boy, but here's the problem: his roommate was a great hookup. I don't want to be a cold-hearted bitch by hooking up with the bro's roommate (again), but I also don't think it's fair that I have to miss out on a great hookup just because he happens to be friends with the bro. I know there are other fish in the sea besides the bro's roommate and blah blah, but I don't feel like doing a lot of work when I already have a guaranteed great hookup with minimal effort required. I don't feel like giving a shit anymore, so I need you to do the thinking for me.



Dear Lazy,

Let’s look at this from his perspective. He’s probably mad about a few things, all of them reasonable. For one thing, if the shoe were on the other foot, how would you feel if this guy who you admitted to having feelings for over the years snuck in one night and fucked your roommate without either of them giving you so much as a head’s up? It would suck. You say you didn’t “date” but if you’re fucking each other exclusively and have some feelings for each other, guess what, that person is your boyfriend. Maybe not a great boyfriend, but whatever. From where he’s standing, he just watched (or at least heard) his ex girlfriend boink his friend and roommate. I don’t care how over it you are, that’s right up there with “walking on on your parents fucking” on a list of things you’d rather never experience.

Secondly, SatC was on TV late the other night (because writing for this site endeavors to make me as gay as humanly possible), and it was the one where Tom Brady’s baby mama comes home early from the Hamptons to catch Carrie still in the apartment. I think she said something to the effect of “I knew he was having an affair with you Carrie, I just didn’t think it would be in my own house.” Then the bitch broke her tooth, because anyone naive enough to marry Mr. Big kind of had it coming. But anyway, that’s probably what your bro is feeling. It’s bad enough that you’re fooling around with his friend, but you did it in his place. When he said that he didn’t care who you hooked up with (including the roommate), I believe him. I just think he left off the second part “… just don’t do it here”.

This isn’t difficult: Just hook up with his friend at your place instead. That way, no one has to ask questions they don’t want to know the answer to. I get that a good hookup buddy is hard to find; just clean up your act a little bit.

Snaggle-Toothed Kisses,

Head Pro


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