My Ex Keeps Sexting Me! Sexts and Subtexts with Head Pro

Dear Head Pro,

Welcome to year 3 of the ex that won't quit. He's had several gfs since we split but I still get late night/early AM rando texts whenever the “opportunity arises” (opportunity is putting it way nice). Not sure if its time to reveal these snaps to his gf or keep the lines open for the entertainment value. Thoughts???


Sleepy Betch

Dear Sleepy Betch,

Can we all, if just for a moment, agree that the whole “omg I sent that to the wrong person lol!” thing doesn’t really happen? Seriously, how many times has this happened to you? If you ex is a human being with functional cognitive abilities and not, say, an unusually literate toaster oven, this was intentional. The other possibility is that perhaps he has his girlfriends saved under something other than their names, perhaps the sex acts for which they were the fondest. In that case, for the sake of levity, let’s imagine you are saved as “Rimjob,” and his current girlfriend as “Donkey Punch.” In that situation, ok, fine, maybe it could be a misunderstanding.

While the initial message was clearly unsolicited, you don’t help anything by kind of playing along. The appropriate response after his repeated proclamation of erectile success is something like “you’re disgusting, and that’s inappropriate,” not to suggest he beat his meat, likely to the fading images of prior rimjobs. Think about it, mortified as you’d be at the thought of your current boyfriend advertising his boners to past rimjobbers, would it not be worse if you learned that said rimjobber then discussed masturbation with him? I think so.

Speaking of which, there’s no need to share this with his current girlfriend. The kind of guy whose idea of a come-on is to call attention to his penis and then wait, slack-jawed, for a positive response is by definition not a very subtle person. She’ll likely find out on her own sooner or later, and besides, given you are three years removed from the relationship you are not the custodian of his current one. Your only responsibility is to discourage this kind of thing until he moves on to his next unsuspecting conquest, who will likely be named “Hot Carl.”

Misplaced Kisses,

Head Pro


Dear Head Pro,

I go to college in NYC and started liking a guy towards the end of the school year. We made plans to go out one weekend, then it got postponed to the next, and then the guy flaked. Whatever. I went about my summer at home and visited New York recently to see friends. My good friend was staying at the guy's place one night, and he told me to text the guy to ask if I could hang with my friend for a bit, so I did. He said he had to go to bed early, but he unexpectedly invited me to come over the next day.

Weirdest hookup ever, first of all. It was the afternoon, we were 100% sober, and he wanted to have sex with me. It was incredibly off-putting, especially because the second I said I didn't want to go that far yet, he didn't even want to make out anymore. Soon enough, he gave me some bullshit “studying” excuse and showed me out the door less than an hour after I arrived, and we kissed goodbye. I honestly assumed I wouldn't ever hear from him again when I got the attatched text less than a minute later.

What the fuck?! Is this a poorly worded compliment or a red flag? And what the hell does “not flirting” mean?!


Well Done? (ugh)

Dear Well Done,

So, I’m not really clear on anything that happened leading up to this point, at least not the part where you were visiting NY. Did you have to text this guy to, I don’t know, get permission to hang out with your other friend, or something? Because that’s weird. And then, yes, this happened. Which, again yes, is also weird.

Imagine if you had an acquaintance who you knew always had pizza with her. When she’s in town with her pizza, even though you don’t much like her particular pizza, you figure what the hell, I could go for pizza, and invite her over. In your mind, your friend OBVIOUSLY has to know that this is all about the pizza (since it’s the only reason you ever hung out with her in the first place), and yet when she arrives she says that while she brought pizza, you can only have the crusts. Of course, you end the would-be pizza session early. Afterwards, you send a text thanking her for at least offering the crusts, but under no circumstances are you suggesting you meet for pizza again.

In this scenario, you are the guy in question, and the pizza is your vagina.

When the guy, who you had not seen or spoken to in months, abruptly invited you to hang (solo) at the last minute, what did you think it was for? To have a discussion on the implications of race relations in Western Europe? Now, I could see how, due to the lack of any prior date that there was no way you would think he could possibly expect sex this time around, but this is a college aged guy we’re talking about. The flaking on the date should have been a pretty good indication that he wasn’t that into you, and it’s not as though his heart was going to start yearning for you with the intensity of 1,000 suns in the months spent not speaking to or otherwise thinking about you in any meaningful way.

I’m with you in that the specific way this all went down is particularly befuddling, but it boils down to you going out on a booty call that neither of you thought through very well. It happens, and at least you’re no worse off for it. Plus, now you know you’re a good kisser!

Medium Rare Kisses,

Head Pro


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