How Do I Handle My Large Rotation of Guys? Ask a Pro

By The Head Pro

Dear Head Pro,

So for most of May & June of last year I was hooking up with this guy. Late June I left for Europe for the whole summer & when I got back in late August he was talking to another girl and they soon got in a relationship. I was fine with this of course since we hadn't had anything legitimate, and the only way we talked during the summer was over Snapchat. I hooked up with other guys during the summer & wasn't expecting anything from this guy. When I got home, things were fine. This guy & I have been close friends since then, and even though we probably flirt more than we should, it's been harmless. We've gotten maybe a little more touchy than we should've a few times, but nothing actually bad. He may be a hot, rich bro, but I'm not a homewrecking betch, especially to a girl I routinely see at parties.

Recently, however, he's been telling me he's planning on breaking up with his girlfriend (he told a bunch of people this), how much he wants to hook up, blah blah blah. I was intrigued, but told him to talk to me when he actually grew a pair and broke up with her. When she heard he was going to break up with her and confronted him, he freaked out and apologized and said he must have been bombed (even though he told various people on various occasions) because he didn't mean it. She accepted it like the naive betch she is. Yet the flirting and touching continues, and he won't stop complaining about her to me every time I brush him off. I'm not hurt remotely, I just don't get what the point is when guys do this.


Wondering Betch

Dear Wondering Betch,

I mean, this isn’t that hard. Some people happen to like (or are at least attracted to) more than one person, and some people are scumbags. This guy happens to be both. And don’t act like it’s just guys that do this, either. Regardless of gender, it’s not uncommon to see someone who lacks the nuts to either exit a bad relationship in favor of a better one, or do the right thing and keep their hands to themselves.

Handsy Kisses,

Head Pro

Dear Head Pro,

I recently became single after two basically back to back multi-year relationships. I have literally never been single before and I am so excited/am having so much fun. I know I do not want to date again for a little while (Insert generic: if the right comes along.. maybe.. speech here) but I am planning on finding a nice friends with benefits or maybe quite a few of them, who can also wine and dine me as they please.

Now my question is, what do I do if any of them try to bring up the exclusivity question? What’s the nicest way to say: “I have no feelings and I won’t give up seeing other guys but I like sleeping with you and when you pay for things” (without scaring them away). I don’t want to be the douche version of the typical guy that won’t date their fuck buddy, but really that’s exactly me right now.


I just want a boyfriend in every zip code

Dear Zip Code,

Well, you’re not asking for much, are you? Normally an email like this would annoy me, but this one’s so straightforward and self-aware (for the most part) that I can’t help but respect it. Your plans at this point are probably a little grandiose, but hey, why not? You just got out of two long relationships, so the sky may as well be the limit. Just keep in mind that with casual relationships, much like groupsex, you’ll probably be satisfied with far less than you thought you’d be.

To answer your question, your main (and really only) strategy regarding DTR talk should be avoidance. Guys, when keeping what we affectionately (and respectfully) refer to as “ho-tations,” try to stick to a few rules to avoid that very thing. I see no reason why they won’t work for your *sigh*... Bro-tation (thanks, Obama):

1. Manage your expectations: Not to burst your bubble, but you’re not gonna have a stable of guys who will wine, dine and fuck you whenever you want. Not more than a couple of times, anyway. If a guy takes you out a few times and things don’t appear to progress, he’s gonna want to know what’s up. If he’s taking you out a lot AND you’re fucking, hell, he’s gonna assume he’s in a relationship. That’s the last thing you want. Plus, high-value guys, because they have more experience with women, have pretty finely tuned bullshit detectors for stuff like this. That’s why…

2. Variety is a lifesaver: I mean variety in every sense of the word. For starters, don’t fall into patterns (e.g. don’t make anyone your regular Wednesday bro). That’ll help avoid flipping the “relationship” switch in their heads. You also might want to concede that you’ll have a better time of it if you juggle different guys for different needs. You’ll keep the plates spinning a lot longer if you have, say, a guy or two you can (and only) use for late-night rendezvous, while also a guy or two who you don’t sleep with at all but is great for a really nice evening. Switch things up, and they’ll stay on their toes. Different zip codes aren’t a bad idea, and different venues should be a given because…

3. Discretion is paramount: Guys have a pathological need to brag about our exploits, and it fucks us every time. Don’t fall into that trap. No one needs to know, and don’t get sloppy and think you’re too smart to get caught by the dudes, either. Emasculation is perhaps the deepest-seeded biological fear men have, and there’s nothing more sexually humiliating than finding out the girl you thought you were wooing into a relationship bookended your evening together with a pair of other dongs. The point is, guys are suspicious by nature, and you don’t know who these people know (since you’re actively avoiding building connections with them). Don’t trip yourself up by introducing them to your friends, going to high-visibility places, etc.

4. Be open: Nine times out of ten, these things end up with one person rising above the others and taking precedence. If that happens, great. If you’re too prideful to admit you have feelings for someone, either have the balls (ovaries?) to separate entirely, or just roll with it.

Finally, and this is the only part of your email that’s annoying (Tucker Max stopped being cool like five years ago; a girl version is no better), but you should know how to handle the question if avoidance fails: Tell them you just got out of long relationships, and you’re so busy enjoying single life that you haven’t even stopped to think about anything serious yet. That might mean you lose one of your starters, but you can likely call a replacement up from the minors. C’mon, it’s guys we’re talking about here.

Revolving Kisses,

Head Pro




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