Why Do Guys Make Plans And Then Not Follow Up? Ask A Pro

By The Head Pro

Dear Head Pro,

Not proud to join the ranks of the dumb-ass parade that typically writes you, but I figure if the "is it okay if my boyfriend secretly tapes us fucking?" question wasn't too ridiculous to answer, then neither is this.

I lost a substantial amount of weight over the past year. It feels great to finally be healthy and happy with myself, but when it comes to dating I feel like a 6th grader who got boobs over the summer. Lots of male attention overnight, no idea what to do with it. At 26, I've aged out of the years when it's acceptable to be awkward-as-fuck with opposite sex. I started getting asked out for the first time, but my usually fun-loving, talkative self shuts down entirely on dates and I basically look like this...

For now I'm faking being comfortable as best I can, but here's what I'm wondering: Would it be better to let a guy know after a few dates that I used to be fat and I'm still getting comfortable dating? Is that too much baggage to unload? Would knowing I was fat be a turn-off because they'd worry I'd gain it back? I'm thinking it'd be better tell him the truth rather than letting him wonder if I have Asperger's.


Ex-Fatty Boom Batty

Also, can we all just agree "Self-respect, you fucking idiot" is a more than generous response to the next girl who asks a variation of "Why won't the guy I let casually fuck me whenever realize he wants to marry me already?!?"

Dear… I can’t bring myself to type that,

Meh, you’re never “too old” to be awkward about dating. People, in general, are awkward as fucking fuck, all the fucking time. I mean, look around you next time you’re at an all you can eat buffet a healthy salad joint. Even in simple interactions like paying entirely too much for a salad, people are so awkward about it you’d think they were getting a prostate exam on live television. Awkwardness, particularly when it comes to people you don’t know all that well yet (like a first date!) is a natural part of life. Some men, mostly insecure ones, find your awkwardness endearing because it makes them feel like big manly men with GIGANTIC MANLY BALLS.

So no, you don’t need to apologize for your awkwardness. No one’s going to think you have Asperger’s. I think offering (unsolicited) the information that you were once very fat would only serve to make things much, much more awkward. For both of you. The solution to awkwardness is not to drag the otherwise unawkward party down to your level. Instead, work on making yourself less awkward. That unfortunately involves practice, but it’s a good kind of practice! You just have to talk to more people. Some of them will want to make sex with you, and sex is awesome. If you can overcome obesity (which science at this point basically classifies as an incurable disease), I think you can get over mild social anxiety.

Because calling people “fucking idiots” is the key to sowing the seeds of self-respect,

Head Pro

Dear Head Pro,

I've been single for about a year, and have started running into a weird pattern that I can't figure out. I've met guys (at bars, alcohol involved) who seem to be genuinely interested in me. FURTHER than just general interest, they go through the extra step of making plans with me. I've been inclined to believe that they're genuine guys based on good conversation, things in common, and they clearly aren't just looking for someone to take home because they don't even try and make a move.

The weird thing is that once we part ways, we'll text a little and then the guy disappears! This has happened to me twice in three weeks! Do these guys have any intention of ever really taking me out? The last guy spent like 20 minutes talking just about if I was free the next day and what he wanted to plan-- he didn't want to be too "cliche" and just do dinner and a movie, but wanted to plan something better. Did I hear from him the next day? Would I be writing this if I did? Why bother to make plans with a girl if you have no intention of actually doing it? Is it because they're drunk? Or are these just two strange coincidences?

Is this something guys do? I'm starting to not believe anyone anymore, because the most seemingly genuine guys are making concrete plans and then disappearing into the darkness.

What the fuck is going on?


Maybe it's me?

Dear Maybe it’s Me,

No, they are just drunk and want to fuck you. This is why meeting guys at bars, while convenient, is not necessarily the most efficient strategy for meeting substantive partners.

Call you tomorrow?

Head Pro

Dear Head Pro,

I've been friends with a guy who is eight years older than me for the past nine years. He's known me since I was thirteen. You'll probably do the math...I'm twenty-two. Anyways, he's one of my best guy friends/ "brother." Couple weeks ago we had dinner and drank a lot and started to hook up. He said he couldn't go all the way so he up and left. We texted once and both said we value our friendship more, but he hasn't talked to me since (it's been two wks) probably because he feels bad.

Is there any chance we can still be close friends or did we cross the line into forever awkward?


Drunk Betch

Dear Drunk Betch,

Well. I’m not entirely (or at all, really) surprised that a 30 year old man considered breaking him off a slice of your 22 year old pie. What I find much more troubling is that at one time, a 21 year old manchild was “close friends” with a fucking 8th grader. What did you guys do, read “Tiger Beat” together? Make those little flower-looking hand puppet things that kids use to answer questions that to this day I have no idea how to construct? On the one hand there is definitely value in young girls having older, more mature male role models in their lives, but that’s still really fucking strange to me.

Anyhow, given that you’re both technically adults now, you ought to be able to get over it and go back to being whatever kind of weird “friends” you were before. That’s due, in part, to the fact that you’re (or should be) at such different places in your lives that there isn’t a ton of commonality between you to foster awkwardness. As he marches into middle age as you enjoy your early 20s, don’t be surprised if the nature of your relationship changes naturally. The priorities are just different. You can remain close, but don’t expect to be exactly the same. Just text him, if you want to. What’s it gonna hurt?

How often are you drunk to self-apply the label of “Drunk Betch?”

Head Pro

Got a fucked up question only The Head Pro can answer? Email him at [email protected] and he may grace you with a response. 




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