How Do I Get My Boyfriend To Tell Me Every Girl He's Ever Hooked Up With? Ask A Pro

By The Head Pro

Send Head Pro your questions about life, love and sweatpants to [email protected]

Dear Head Pro,

I've been dating my boyfriend for over a year now and everything is great between us.. But I keep finding out about his past hookups! I feel like every month a girl he has hooked up with comes out of the closet and enlightens me on his past. Even one of my friends that I have now has hooked up with him. She made me promise I wouldn't get mad!

He grew up in the town we live in and I haven't lived here too long. It seems like the people who grew up here have all pretty much hooked up with each other. And it's totally normal? Small town? IDK, I thought that was weird. I told him I want to know everyone that he's hooked up with that still lives here so I don't have to be "surprised" again. I feel so naive when girls I have become friends with and they tell me his past that I have no clue about. So I've been bugging him about it lately. But he thinks it's none of my business and I'm just being nosy!

Is it wrong for me to want to know? He is totally all about me now, but I feeling he's like already been with the whole town! and I want to know...


Prying Girlfriend

Dear Prying Girlfriend,

The thing is, you don’t actually want to know. No answer he could give you would ever be satisfying, because imagining our significant others getting up in other peoples’ sex parts is an inherently unsavory proposition. That’s doubly true when you want him to outright doxx them, because presumably you’ll have to see these people again. Having grown up in a small town myself, I can attest that they’re sometimes gross, incestuous places - it’s just what happens. But your boyfriend is right: It’s none of your business. Outside of a clean bill of sexual health, he’s under no obligation to provide you with a detailed sexual history. You don’t want to see what he’s been making with his sausage.

Your reasoning is sound in that you want to avoid getting blindsided with these sexual surprises, even if intellectually you know they have no bearing on your current relationship. I would understand if you’re being ambushed by girls taunting you with “hey bitch, how’s my gash taste?” but that’s not happening. In fact, the only incident you cite was when the girl offered this information not out of malice, but what appears to be a gesture of honesty and friendship. To me that sounds like the least-jarring way to be confronted with that information, far less so than being presented a laundry list of girls he’s fucked.

More importantly, what would you do with this information? At best it would feed into your own insecurities and paranoia, and at worst you’d use it (subconsciously or otherwise) to restrict his social circle. Imagine the reverse scenario, where your boyfriend was shaking you down for a sexual history. How would you feel? You say your relationship is fine, so all you’re doing is looking for a solution to a non-existent problem to satisfy your own curiosity.

You can almost certainly badger him into spilling if you make a big enough scene about it, but he won’t be happy about it. Ultimately, neither would you.

Secretive Kisses,

Head Pro


Dear Head Pro,

I need some help with college boys. I'm a freshman betch who was a little too good at not fucking bros throughout high school, so I'm still a virgin (which I'm fine with; I just never found the right guy). But now I'm surrounded by so many new people and I've found this guy that I really like.

We've hooked up a couple of times, and we've done everything but had sex (even sleepovers). He knows I'm still a virgin and is totally fine about it (very respectful etc.) but has told me he wants to go there with me. I would be completely down because I really like this guy, but I'm just not sure what will happen to our semblance of a relationship if I do decide to do it with him. I'm not really looking for the first guy I have sex with to be a casual thing, because I think I want something a little more serious, but I'm not sure how feasible the non casual part is.

So I guess my question is whether or not it's reasonable to think that this guy will understand that my first time is a big enough deal to me to warrant something a little more serious than a booty call situation. Even though that isn't what it is right now, I'm nervous that he's just waiting for me to give it up, and once I do he'll think of me as a one and done.

Any advice would be great!!!


(Soon to be not?) Frigid Freshman

Dear Frigid Freshman,

If you want to fuck the guy, then fuck the guy. He doesn’t sound like he’s trying to pump and dump, and I say that for a few reasons: One, it’s unlikely that he’s been biding his time waiting to get his dick wet and bounce. Guys don’t realllllyyy do that, especially not on college campuses where casual sex isn’t exactly a rare commodity. Two, there’s a difference between a guy saying he respects your virginity and actually doing so. He sounds like the latter, which is encouraging. Finally, sex isn’t some kind of “on/off” switch that causes men to immediately abandon the notion of commitment. If anything, it’s the opposite - humans tend to use sex as a bonding agent. While there are certainly men who exploit that for their own sexual benefit, they aren’t the norm and honestly it’s difficult to know who those guys are, outside of reputation and the rumor mill.

To each their own, but I feel like you’re being a tad too philosophical about the whole thing. It’s odd to me to think of sex as a flowchart, where if you do X, then you want Y to happen. I mean, that’s just kind of how life works - sure, people divert to blow jibbers and fingerblasting because it’s perceived as less intimate, but the point is still “I like this person, and so I want to escalate with them physically.” If you go through life basing sexual decisions on a million different, hypothetical variables, then you could talk yourself out of having sex with practically anyone.

If you want more assurance, you can (and should) basically tell him what you told me. Girls use the “I don’t fuck people I’m not in a relationship with” all the time (whether they mean it or not), so it won’t come as some shocking revelation to him. It’s a reasonable point to make, and how he responds should tell you something about his intentions.

Jittery Kisses,

Head Pro

Dear Head Pro,

Cutting to the chase in hopes to not make this a long drawn out email, met a kid, hooked up with a kid, woke up next to said kid, am still somehow talking to said kid weeks later. We have a date planned, but I wanted to know what bros think about a girl who wants to be pretty much exclusive... But kinda just wants to skip to the watching movies/boning part instead of the whole dinner-date shit. Like I already drunkenly slept with the kid, and really all im looking for is a movie-make out (and whatever else) buddy, but without being disrespected. Do I have to make him play the game to be treated well, or can I just skip to the (in my opinion) fun shit?

Thanks a bunch,

Idon't have a clever name

Dear Lazy,

So, the way I read this is that you want to dive immediately into the lame, boring parts of a relationship, something that takes years to develop and something most couples fight tooth and nail to avoid? Couples get to that point after a long time, where familiarity has caused the newness and electricity to die down a bit and become replaced with a different (though arguably better) sort of love and affection. You don’t “kinda” want to skip the courtship parts, you LITERALLY want to skip into the late stages of a relationship, complete with the exclusivity clause. You strike me as a very odd lady.

The exclusivity thing is what makes it weird, as it’s not all that difficult to find guys who want to watch movies and fuck you. You have to understand that courtship isn’t just something guys endure so they can get to the land of reliable sex, sweatpants and pooping with the door open. Dating, after all, is supposed to be fun. Sure, there’s the conventionalism and status demonstrations that lead us down the familiar paths of movies, drinks and expensive dinners. But, by trying to shoehorn this guy into the doldrums, you’re denying him (and yourself) the opportunity to experience the sort of shared bonding that leads people to become perfectly content with the sort of relationship you’re after. You have to EARN the right to fart under the covers, dammit.

I honestly don’t know what to tell you. Your best bet is to slow-play things, offering movie nights at your place in favor of nights on the town until exclusivity becomes a topic (or at least implied). While you don’t necessarily have to play the game to earn respect, doing things in a non-sexual environment so that he can grow to appreciate you as a person is kind of the point of dating.

Netflix Kisses,

Head Pro

Send Head Pro your questions about life, love and sweatpants to [email protected]




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