Sexts and Subtext with Head Pro

Your Mighty Pro-ness,

This guy and I have hooked up on and off for almost two years. (No sex, we agreed not to mess our friendship-hook up with the feelings that come with sex). We've been on and off obviously when we both have other people. And we're honest about it. So this fun little screenshot is from around Thanksgiving where he admits to being involved with a chick (and says she “isn't perky like me”- yes he's referring to my perky lil bum [humble brag]) and then today says he misses me and can't wait until I'm done with finals and back in the city to hang. What's this bro trying to do? he works in CT, and I'm in law school 2 hrs away. P.S. the age reference is his preference for girls 6+ years younger than him, or cougars.

All the best,

I hope feelings aren't contagious.

Dear Contagious,

There’s so much more I’d like to know about this bro. For one thing, who’s into cougars anymore? If I wanted to bang the barren, empty husk of a woman, I’d just go back to banging your mom (zing!). Also, what straight bro in his right mind agrees to not have sex with someone for an extended period of time so as to “not mess up the friendship”? A two-hour commute for some making out and the occasional fingerblasting sesh? Well hot damn, where the fuck can I sign up for that? On a side note, I think you’re being presumptuous thinking his comment about perkiness refers to your “bum.” Who talks about other girls’ asses with a girl they want to bang and/or fondle? And who says “bum” outside of old British people? So many questions!

The reality is (probably) this: You’re in NYC or Boston (if being in CT puts him two hours away), which are pretty hip places (so the kids tell me) that I’m sure he likes to visit. When visiting a place you don’t live in, it helps to have someone to visit. Otherwise, you’re just a lone tourist (gross). Secondly, for two people to maintain a sexless, long distance pseudo-relationship, at least one of them has to have some emotional involvement. Since you claim to be the sensible one who wants to avoid going down that rabbit hole, my guess is it’s him, and he probably has for a long time. The fact that he distracts himself and his dick with women much older and younger than himself tells me that his serious relationship intentions lie elsewhere, namely with you and that big beautiful vagina of yours that he has yet to experience with the proper organ. Does that interest you? Cool, then go ahead and take that first ride on the fuck coaster and see what happens. If not, just understand that his intentions won’t change until one or both of your situations do.

Either that, or he just really wants to do sex with you and he’s trying a new tactic.

Perky Kisses,

Head Pro

P.S. There's only one text today because it's the holidays and I'm therefore not into doing work. Promise I'll try harder next time.

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