Is My 35 Year Old Boyfriend Into Me? Sexts and Subtexts with Head Pro

Dear Head Pro,

I met this guy at a party last fall and we've been casual acquaintances ever since. We have some mutual friends and have occasionally texted/messaged but he's more or less just someone I sort of know. He also happens to be totally hot and a friend of his suggested we get together last year but obviously nothing happened. I've got a crazy schedule and have no time for relationship bullshit or anything even remotely serious or committed right now. You think I'm just saying this, but I'm not. This betch just wants to have fun.

A few weekends ago I got blackout at a party and (apparently) told another of his friends something that prompted the attached message (what I said is mystery). My friends all thought it was–like super sweet!–but I think they're fucking stupid because to me it reads as a polite rejection even though I didn't ask for anything. I really have no idea what his last line is about, though I'm guessing he thinks I want something beyond a hook up. Can't a betch just get it in without every guy thinking she wants a ring on it the next day? And even if he's not interested, why bother acknowledging my blackout, unfiltered thoughts? I have a class with kid and it's fucking awkward even though we both agree to ignore the whole thing.


Thanks But (No?) Thanks

PS The accent thing is from a medical sob story. He knows this but I'm mortified he mentioned it because no guy has ever outright acknowledged it.

Dear Thanks But (No?) Thanks,

Oh Christ, another one of these. “All of these guys want to have a relationship with me, and I just want to have fun because I think I’m a fucking ‘Sex and the City’ character mew mew mew,” you complain, meanwhile every normal girl is at home lighting torches and sharpening farm implements, hoping they can use the geotags in your screenshot to determine your location.

This is, I’ve decided, the girl version of the friendzone. When guys say they’ve been friendzoned, they say it because a woman they want to fuck likes them, but not enough to fuck them, and so they end up in the “friendzone”, as though having someone else in this world who cares about you at least a little is the worst fucking thing that could possibly happen. With girls, it’s the same thing but somehow worse. “UGH, why won’t this guy STOP LIKING ME ALREADY and just use me for my body!?!?” Right, because someone wanting you for something other than a receptacle for his baby sauce is, in the grand scheme of things, terrible. Like, I get what you’re trying to say, but enough with this shit.

Anyway, for someone who acts like she just wants a mechanical penis that she can ride while she studies for her finance midterm, you seem awfully concerned about a pair of seemingly innocuous text messages. Yes, his mention of your impairment is forthright and possibly a little rude, but what he’s really saying is “I acknowledge this weird aspect of you, and it does not make me uncomfortable. I like you not in spite of it, but because it’s part of you.” Awkward, but obviously not the worst thing that could happen.

Of course, the bit at the end all depends on whatever it is you said. If you drunkenly expressed a desire to share lots of children and a house with him, then yeah it might be a rejection. But, given your apparent disposition and predilection towards “just having fun,” you probably said something along the lines of “I want him to fuck me so hard the house collapses on us as though a tornado hit it but we’ll keep fucking anyway because that’s how much fucking I want him to do to my areas.” In that case, he’s not rejecting you so much as he’s telling you he’s not that kind of guy and sees something he likes in you (that isn’t his dick). If he was flat turning you down, I see no reason for him to head into awkward lisp territory.

Whatever result you’re after, the next time you see him just relax. The worst scenario is that he maybe, sorta, kind of likes you.

Unfiltered Kisses,

Head Pro

Dear Head Pro,

So here's the sitch…I'm 25 and have been seeing and #sometimesfucking a pro who is 35 for about 2 months now. 

He has the 4 B's that would peak even the iciest betch's interest – Body, Brains, Boat, and Bank Account. 

A few questions here – if a handsome, successful guy is still single at 35 is there something wrong with him?  Is the fact that he is dating a 25 year old a red flag?  Am I barreling towards a dead end?

In the interest of self-preservation, I've implemented classic betchy moves including but not limited to – delayed response times to text messages, not picking up every phone call and so on…but like in my attempt to play it cool, I've gotten the hot and cold treatment in return.  Days will go by without contact followed by multiple calls and invites to hang out.

To add to this mindfuck within a mindfuck, he has started saying “I love you” — I mean like the jig is up…you've been in me, you don't need to throw that shit out there.  He also sends texts like the ones attached when I ignore him because he has just gone dark for a few days.

Like what?? 



dazed and confused


Dear Unoriginal Pseudonym,

This might win the award for “Least Descriptive Screenshot,” but that notwithstanding I don’t think you have a whole hell of a lot to worry about and most of your fears are largely unfounded. Let’s address them:

– If he’s 35 and has his shit together to this degree, I doubt he spent his 20’s chasing skirts and drowning in whiskey. Some guys kind of lose sight of the bigger picture and wake up one morning and say “shit, I’m 35 and single.” Either that or he’s queer as a $3 bill.

– If you were a 35 year old guy who was in good shape and didn’t look any older than you actually were, you’d probably set your sights a little younger too. For thing, if you can get it, why not? Also, he might want to have children someday, and given that that usually takes time to come to fruition, he probably doesn’t want someone who’d be trying to have their first kid at age 40, if he can help it. Other than that, you’re 25 (not 15), and he’s 35 (not 50). There’s no reason your interests can’t overlap.

– The “I love you” thing might be a little scary/off putting to you, but that’s because you’re 25 and still have that high school mindset where the thought of using a particular word to describe your feelings for someone was, to that point, the most important, grown up gesture of your entire fucking life. Being able to truly love someone is as much about being able to love yourself, so as a successful 35 year old man he’s probably pretty comfortable with his place in life. He may be unlike Forrest Gump and not know what love is, or he may just know what he wants and isn’t afraid to say so. Either way, it’s unlikely to be the underhanded/desperate gesture you’re seeing it as. Speaking of…

– The idea of guys seeing sex as the goal/endpoint of a relationship is kind of overstated/misunderstood. Not many guys will sit there and form a strategy like “I’m going to meet this girl, wear her down, and then stop talking to her as soon as we fuck.” Most people don’t have that kind of time on their hands. For a guy to put in that much work, they have to like you as a person at least a little. It’s possible their feelings will fade before too long, but it’s unlikely (especially in this situation) that he’s using words as a tool for sex. Really, the fact that that was your go-to explanation tells me you’re probably not ready for whatever this is.

So, yeah, it sounds like this guy is just really into you, if not a tad overzealous. I think the “mindfuck” is all in your head, something you’re using to create drama that isn’t actually there. If you’re actually into him, grow up, have a conversation with him like an adult, and see where things go. Otherwise, go join a coed kickball league or whatever the fuck it is recent grads do to meet people.

Geriatric Kisses,

Head Pro


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