At What Point Mid Hook-Up Should I Tell a Bro I Have My Period? Ask a Pro

Dear Head Pro,

What happened to guys waiting on girls to be ready to have sex? I'm going to turn 24 soon, and many assume that the older you get, the less time it's acceptable to wait around. I'm getting frustrated with guys thinking that just because you're not 20 or a virgin, holding off on jumping into the sack after a couple of weeks of seeing each other is not an option.


Chivalry is Dead?

Dear Chivalry is Dead?,

Wait, so are you saying that the guys you’re meeting aren’t waiting for you to be ready for sex but are doing it anyway? You seem remarkably calm about that. I guess what you’re saying is that guys are dipping out after a couple of weeks of dates when you tell them sex isn’t in the cards? Because if so, welcome to life. Of course you’re not under any obligation to have sex with someone, not because you’re of a certain age or because you aren’t a virgin or any other reason beyond not wanting to. Keep in mind, though, that they aren’t under any obligation to hold out for your as-yet-unknown threshold, either.

In general, as people get older sex ceases to be the Big Deal it was whenever we were first having it. You don’t get the same thrill out of having a drink now as you did when you snuck your first beer, do you? Still, people have their limits and proclivities, which is fine. You want to slow play it with sex, and that’s your right, but you’re misreading the situation a little. Guys aren’t eager to have sex because “chivalry is dead,” they’re eager to have sex because they’re ALWAYS eager to have sex and their experience leads them to believe that it’s something two consenting adults want to do together after it’s established that they like each other.

Consider too that beyond wanting sex just for the sex, guys want to be with someone who actually wants them as much as girls do. If every other girl they date jumps in bed with them after a week or so, they’re just going to assume you don’t like them all that much. And, considering you’re not into them enough to sleep with them, they’re kind of right. I’m not saying you’re “wrong” for waiting a long time to have sex, I’m just saying that you’re not going to run into billions of guys who have the patience for that. You’re obviously looking for guys who are open to something somewhat serious, which is statistically going to be harder to find regardless of whether or not you give it up easy. If not fucking guys who might not be “the one” makes you sleep better at night, that’s fine, but in that case you also don’t really have anything to complain about.

Chaste kisses,

Head Pro


Dear head pro,

A lot of my closer friends are a couple years older than me, and of legal drinking age whereas I'm in my senior year in high school. So they got me a fake and I tag along wherever they are going that night. If I ever meet or hookup with a guy, I lie about my age considering it's usually a one time thing and I never see/talk to them again.

A couple weekends ago I met this guy in his early 20's and we really hit it off and I've always taken a liking for older guys. We've been texting and he wants to hang out soon but he thinks I am older then I am. Should I tell him my age and come clean or just keep up the lie, seeing as it probably won't go very far, just a casual hookup here and there. Any advice?


Dear Underage,

Oh goddammit, no. No, you do not just lie because it probably won’t go very far. First of all, who are these 21+ year old people who claim to be “close friends” with a high school student? These people should be at least halfway through college. It’s not even your older siblings, or at least you don’t say so. The people you hang out with are weird for hanging out with you. That’s a shitty thing to say, but it’s not your fault. It’s theirs. Keep their fake and find less-weird friends.

But no, do not lie about being older than you are, PARTICULARLY if you’re a minor (I guess you could be 18, but I don’t know). Just drinking and going to bars with this guy could expose him to a whole litany of legal breaches, whether he hooks up with you or not. Beyond that, deception is just not a good way to start any kind of relationship, even a casual one. Like, if the guy’s going to turn tail when he finds out you’re not 21 or whatever, that’s probably a good thing for both of you. What else would you lie about to keep his interest? Your name? Any potential family connections…?

Tell him how old you are, and tell him specifically that you’re in high school. If he’s really considering going out with you, he has a right to know at least that much, especially since you already established a false identity versus some “lie of omission” bullshit. You were in a bar. He believes you to be 21, but you are not. Who knows, when you confess, maybe it’ll turn out that he’s also underage and you go to the same school AND you’re actually cousins! I SMELL A PRIME-TIME TELEVISION DRAMA.

Statutory kisses,

Head Pro


Dear Head Pro,

I personally am all for period sex, but I know some guys can be a bit squeamish about it. My question is, if I am hoping to hook up with someone, and am on my period, what is the etiquette about letting them know. Do you let them know as soon as they asked you to their place for a “movie” or a “drink”, do you wait until your underwear is almost off, is there a standard operating procedure? I assume some women just avoid hookups at that time, but for those who are not in the mood to wait, what is the best way to broach the subject?

(I feel dumb for asking)

Best Regards,

Shark Week

Dear Shark Week,

Oh Lord that is just terrible. Seriously though, I don’t know why some people take such issue with period sex. I mean, of all the bodily fluids down there, you’re going to scoff at plowing through the one that’s clearly identifiable? Bullshit. Worse are the guys who are all “mew mew mew, I don’t want to get my sheets all messy.” Broseph, THAT’S WHY GOD INVENTED SHOWERS WITH ROOM FOR TWO PEOPLE. Any guy who balks at period sex for the sake of his sheets is less than a man, and is doing you a favor.

Anyway, you probably want to spill the beans somewhere between the two poles you suggested in your email. Upon the invitation for a “movie” or “drink” is probably a little presumptuous, but the last minute doesn’t give us much time to get the hot water going, or at least put a towel down. I’d let him know when things are clearly heating up, but before all the clothes come off. That will give you time to do that thing where you kind of awkwardly mumble-discuss it between kisses, where you’re both trying to sound sexy, even though there’s to sound sexy when you say you’re bleeding out of your crotch.

Sanguine kisses,

Head Pro


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