My Former Fat Guy Friend Won't Ask Me Out: Sexts and Subtexts

By The Head Pro

May 6, 2013

Dear Head Pro,

A while ago I was hooking up with this guy, he was great and I kinda wanted to get to know him better. Out of no where he calls it off, I was crushed. Fast-forward 1 month and I found out it was another girl he had some history with that he is with. She is out of the state, but he is trying "not to screw things up"

While he is all about this girl it doesn't stop him from texting me about how much he wants me. Is this cheating? I think it needs to stop and he's a creep, what do you say?More importantly how to I get him back for treating me for being the butt end of the expression "have your cake and eat it too."


Dirty bird

Dear Dirty bird (why?),

It doesn’t really matter whether I, you, or he thinks it’s cheating. What matters is what his girlfriend or whatever the fuck thinks, and my guess is she would probably think it is. So, yeah, he’s cheating. Whoop de do. Not your problem. Though you are not the custodian of his relationship, it probably should stop, at least to absolve your conscience of all wrongdoing (if you care about that sort of thing). The first step is to stop texting him pithy shit like “you’re teasing me”, or expressing your desire to show him your boobs. That’s not helping anything, which is rare because in my experience boobs usually solve everything.

The second step is to drop the “but you have a girlfriend” line of thinking. He knows that, and he’s doing it anyway. All you’re doing is feeding into whatever insecurity he has. The key is to compound that insecurity with even more insecurity and emasculation. Next time he texts, ignore him for a while. Then, when he gets impatient, respond with something like “Dude, we hooked up like xx months ago. Let it go.” He’ll come back with something like “Oh but I just can’t get you out of my head bla bla bla backpeddling bullshit.” When he does, respond with something like “Cool, bro. Get on tinder or something.” Boom. You mean nothing to him. His ego dies a thousand douche deaths.

As far as revenge goes, first of all grow up. It’s not like you were the one he cheated on. Secondly, you can’t exactly un-fuck him, so any extreme course of action would make you look more pathetic than these text messages already do. The best thing to do is to make him feel small, like the kids in “Honey I Shrunk the Kids.”

Teasing Kisses,

Head Pro

Dear Head Pro,

I've known this bro for almost 10 years. In middle/high school, he was the potentially cute, sorta-chubby kid who constantly complimented me and listened to me nag about other guys. We've had a few drunk run-ins recently but we have never hooked up. He has admitted he likes me but he isn't looking for anything serious. A few weeks ago, I ran into him outside of a club and kept things super short. Ten minutes later, he sends me this text. I have heard nothing from him since that night. What is his deal?

LA betch

Dear LA betch (OMG you’re the only one?),

So, like, what’s your deal? What exactly are you asking me, or what do you want out of this bro? If he always listened to you bitch about guys and was paying you unsolicited compliments, he obviously had a crush on you and was prob too chubby to have the confidence to do anything about it. Is he a stud now or something, and that’s why you care? I don’t get it.

If you’re saying you want him to make a move and ask you out, good luck. A lot of times, fat kids get skinny, but they’re still a fat kid trapped in an Adonis body. Even though they look good to everyone else, they still lack the confidence to step up and crush some kitty. Even when they do have the confidence, they’re still usually terrible at sports, so you can still make fun of them. It’s really a win-win.

If you want this bro to ask you out, if this is what he managed at 2:00 am, that’s probably about the best you’re going to get out of him. If the hours between midnight and 4:00 am ceased to exist, the human race would literally die out because no one would be getting laid. Considering the best he could muster was the implication that you two might see each other at a planned time and place, that doesn’t bode well. He’s probably more trouble than he’s worth.

Chubby Kisses,

Head Pro

Got a text so perplexing that only the Head Pro can interpret? Email him at and don't forget to follow him on twitter @betcheheadpro.







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