How Do I Tell My Date About My Incurable STD? Ask a Pro

Dear Head Pro,

So I'm pretty embarrassed to be asking this question, but it's something I'm very worried about and would love a male opinion on.

My ex-boyfriend gave me herpes pretty early into our relationship, and while he was an ass for not telling me he had it even though he knew, it happened and I've gotten over it.  2 years later, we've broken up and I'm ready to start dating again… I've met a guy who I really like and we've been talking/flirting a lot for a couple of months.  He finally asked me on a date the other day, and while I'm thrilled because I'm very interested in him, I'm actually really really nervous because I don't know how to deal with the herpes situation.

When is the appropriate time to tell him?  I feel like the first date is the wrong time because that's basically going to ward him off straight away, but how long do I wait?  I'm afraid that with the holidays coming up I'm going to get myself into a situation where we're both drunk and go back to one of our apartments to hook up and I have to stop it and explain everything, which is definitely the wrong time.  Basically, how many dates in should I drop the H-bomb?

Infinite thanks,

Infected Betch

Wow, what a shitty thing to have happen. At least in this case, what you’re talking about is just a date. It’s unlikely, then, that sex will be on the agenda, which is obviously a good thing. I would advise giving him time to get emotionally invested in you before you broach the subject, so maybe plan for many, many dates before you cross that bridge.

When the time comes, just make sure you don’t get stuck having to explain things when you’re about to hookup, and preferably not when either of you are drunk. Just be clear and honest about what it is, how you got it, and what the implications are. If the guy’s into you and worth a shit, he’ll understand that it’s just a thing that happens to some people and there isn’t anything you could do about it. It’s up to him how he chooses to proceed, but you have a much better chance of handling it well if you have a solid foundation first.

Dear Head Pro,

I've been seeing this guy since the summer. Recently, we had the '“what are we?” talk. Neither of us want a relationship right now, so we agreed to keep it casual. He's always been respectful and all about me when we go out, but I don't know what happened last night. He texted me asking me to come to this bar, and I told him I was probably going there with friends later. He texted me again saying he was heading over to the bar and asked where I was, and then sent another “where are you?” text. When I get there, he gave me a hug, but he wasn't super talkative. He looked at me and whispered something to his friend.

He was being awkward so I went to say hi to other people. He started talking to another girl for most of the night. He wasn't all over her or anything, but he kept looking at me as he was talking to her. I can't tell if he was trying to get a reaction or if he was making sure I wasn't watching him. Either way, it was very rude. I don't care if he hooks up with other girls, but I don't understand why he would invite me if he was going to blow me off. Did he invite me and this girl thinking he could be slick? Before the bar closed, I acted normally and hugged him goodbye because I didn't want to give him a reaction. Should I ignore him now? I've never been in this situation so I don't know what do.


Why do I always pick the dingbats?

Bla bla bla bla, I’m mad because the boy I like was talking to another girl, even though I’m going to pretend I’m mad about something else because I don’t want to admit that I really do want a relationship because otherwise I wouldn’t be asking this stupid question.” I think that sums it up. Also, quit with the hugging bullshit. I fucking hate the type of guy who gives hugs to girls as a greeting. It’s weird.

Dear Head Pro,

I recently met a guy while out.  Early on into our acquaintanceship, he told me he has a girlfriend who doesn't live around here.  We danced for a good part of the night, sharing minimal facts about ourselves but otherwise enjoying each other's company.  When it was time to leave, we exchanged numbers.  He texted me later in the night, and I responded by calling him out for having a girlfriend.  He brushed it off as junior high for her to care about dancing with me, and we continued an amicable conversation from there that ended not too long after.  The next day, he texted me to say he and his friend's would be out again; I didn't respond.  I went out with my friends that night and saw him again.  We danced again, talked more, and I went home with him.  Things were pretty hot and heavy when I started to feel crap-your-pants queasy… Let's skip the gruesome details, and I'll just let you know that since I couldn't find the matches, there was no way in hell he didn't know what went down in his bathroom.  Mortified, I left shortly after and sent a quick text apologizing (not referencing any specifics of course).  He didn't respond.  A couple days later, I received a text from him asking if I'd like to go to dinner with him.  I really like this guy from what I can tell, so I have a couple questions:

1.  Is he really into me or does he still just want to get in my pants and that's it?
2.  If he is into me, how do I broach the subject of his girlfriend/should I be worried about his moral compass (and mine)?
3.  I thought pooping in a guys' house was THE biggest faux pas.  Have I been ruining my digestive tract for no good reason?


I wouldn't call it diarrhea, but it was borderline…

My favorite part is, after all of the pooping and the very real moral handwringing, the first question is “Is he really into me?” How the fuck should I know? He’s apparently “into” his girlfriend enough to call her his girlfriend, and he’s still cheating on her.

Anyway, why is this a question? Why do you “really like” this guy when one of his qualities, one of the things that are true about him, is that he’s cool with cheating on his girlfriend? You can’t rationalize it by being all “well, he’d be perfect if it weren’t for that.” Maybe so, but is IS for that, end of story. Don’t fuck with people who are in relationships, no matter how cavalier they are about it. It’s not a good look.

Dear Head Pro,

I'll get straight to the point, I smoked with this bro all weekend and while we were watching a movie all of sudden he says “I'm gay.” with a completely straight face. He didn't laugh or anything. Obv I awkwardly laughed and said “yeah, right.” At this point we haven't slept together (everything but), because I'm making him work for it like a true betch. A couple of blunts just isn't going to cut it. But now I'm questioning if he really meant it?



Holy shit, what? You’re “making him work for it like a true betch?” Work for what? Dude said he’s gay. I don’t think he’s buying what you’re selling, dear. Just because you guys have fooled around and he appeared to enjoy it, that doesn’t negate him being gay. It’s very possible that he’s been in the process of coming to terms with his sexuality, and maybe part of that for him was experimenting with both teams. I don’t know. I don’t know how all that works, but I do know that if someone tells you they’re gay, one of the rudest things you can do is be like “haha naw bro, no you’re not.”

Merry Christmas, everyone


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