Relationships Talk

Animation by Lisa Larson-Walker. Photos by Getty Images.

How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to howtodoit@slate.com. Don’t worry, we won’t use names.

Dear How to Do It,

I am the guy who did the stupid thing from a hundred overheated online stories: I slept with my straight roommate when we were both drunk. I am the only gay guy (seemingly!) in a shared house of five guys, and this was very much unplanned. I was totally fine with it, and he acted like he was too, but it’s clear he’s not. A month later, I now hear him having loud sex with women regularly, which I definitely never heard before. He’s not hostile, but he won’t really look me in the eye either. The other roommates have asked me if I’ve noticed him acting strangely. Is it wise to bring this up with him, or should I just let it go? Again, I know I am dumb.

—Straight Shooter

Dear Straight Shooter,

The best immediate course of action here is to relax. Stop beating yourself up. It’s not dumb to hook up with a self-identified straight guy; it’s hot. You (presumably) introduced him to the joys of gay sex, and he clearly wanted to learn sometime. What was on the “dumb” side (to use your word) was hooking up with a platonic roommate, as now you have to look at him not looking at you every day.

Like many of life’s pleasures, hooking up with a straight (or closeted) guy comes with a cost. The price you pay for hooking up with someone who is less than secure in his sexuality is the awkwardness that comes after. Let him sort this out on his own, or at most, let him make the first move. (This, by the way, is a good rule of thumb for handling “straight” guys in a sexual capacity in general.) On your end, I do not think any further action is warranted at this time.

But, man, if he is really banging chicks loudly to send you a message, it means he’s thinking about you when he’s having sex, which means you rocked his world. Relish that. It’s likely all you’re going to get out of this, so might as well appreciate what you do have.

—Rich

Dear How to Do It,

I’m a woman who recently started seeing a guy who is not at all my type—jock-y, clean-cut, works in finance—and found myself desperately wanting to have sex with him. I can’t even look at his thighs in pants without thinking about it. But while I’m used to guys coming on strong, he is not one of them. He told me he likes to take things slower, and I complied. We didn’t get naked until the fifth date. That night he told me he wanted to avoid penetrative sex “for now” (forever?) because it makes people get “too attached.” We have oral sex, which is nice, but isn’t this strange? I’ve asked him to elaborate, but he just says “that’s his experience” with penetrative sex. Twist: Recently, drunk, he told me his fantasy is to bring a third guy in to join us—who would presumably penetrate me.

—Inner Conflict

Dear Inner Conflict,

There’s a lot going on here, but I worry the real issue is on your end. It sounds like you’re feeling frustrated desire, especially in your parenthetical. But I urge you to be cautious of invading his boundaries, including psychologically. His avoidance of penetrative sex and his threesome fantasy could be preferences, or kinks, or they could point to something deeper. He might not feel comfortable elaborating. Sometimes people aren’t ready, or had a negative experience they still aren’t in a place to process.

As for you, well, it can be really hard to spot the red flags or plain-old core incompatibilities when your vagina is screaming at you. If you’re getting a faint vibe, it might be your instincts trying to protect you. Then again, I don’t know how often your “strange” meter gets checked, much less how often it’s right. Have you had big divides with sexual partners before, and what happened then? I would think about how confounding he—and your strong against-type desire for him—seems to be for you.

While you’re thinking about those questions, consider a sex toy, get back in touch with your own body (by which I mean masturbate copiously), and maybe talk about your overpowering sexual desire here with a therapist.

—Stoya

Dear How to Do It,

On a recent trip abroad, my husband and I, feeling emboldened by a few glasses of wine, went into a sex store and bought a sex toy. It’s nothing too crazy, but definitely crazy for us: It’s a vibrating ring that’s supposed to go around his business. It’s now been five months, and we still have not used the thing. It’s so easy to get into a perfectly enjoyable, reliable weekly routine when you’re married that I think we’re just both finding it difficult to improvise. What are we waiting for? Do we need to have a conversation about it beforehand? What does it mean that neither of us has as of yet taken the initiative to produce that vibrating ring and declare that Now’s The Time?

—Tool Time?

Dear Tool Time,
I think what it means is that neither of you are that interested in using this toy. If you were, you’d be using it. People don’t procrastinate stuff that they actually want to do. Right now, it sounds less like a fun prospect and more like something that is haunting you like a tell-tale heart under the floorboards. Except it’s coming from your underwear drawer and it really is making noise because you knocked it on the last time you were getting dressed.

If your weekly routine is indeed perfectly enjoyable, surely this added stimulation isn’t needed. But if you are genuinely curious and hung up on this thing for practical reasons (and not merely the principle of it burning a hole in your underwear drawer), I think it’s up to you to bring it up. For one thing, you care enough about it to ask a stranger for advice regarding it, and for another, from what I understand, these kind of toys can be way more pleasurable for women (and their clitorises) than for men (though certainly, they get the extra stiffness that the cock ring component provides).

And hey, maybe your dude is the kind who would totally get off from the incessant stutter of a vibrator perched around his junk. That would be interesting and, hey, there’s only one way to find out. Crack open a bottle and see.

—Rich

Dear How to Do It,

What is a non-weird way to ask new partners whether they’re clean? I don’t want to just ask people for their medical information, but I want to stay safe while I’m screwing around.

—Safe Word

Dear Safe Word,

“Weird” is fantastically subjective. You clearly want me to give you an easy, fast way to get the conversation out of the way, but I’m going to do the opposite. Gather ’round.

Safety is a lot more complicated than “Was your last test negative?” When you’re mashing body parts together that we don’t usually even show each other, there are a lot of risks. You’ll need to ask questions about specific high-risk behaviors (what fluids you’re willing to allow where, whether you’ve had multiple partners recently, to name a couple) and get an idea of how well the person you’re considering having sex with keeps track of these things. You’ll have to observe their behavior, and you will at some point probably need to make a leap of faith.

There are window periods—spans of time between exposure to a bacteria or virus and a reliably positive test result—that mean you need to take the sexual activity before the person’s most recent test into account to evaluate the risk. There are also risks we think about less than, say, chlamydia. Mono can be passed through kissing, but because we don’t stigmatize it, we aren’t as afraid of it. (A note on that stigma: This is not an original point, but don’t use the loaded word “clean” to mean STD-free. When you do, you’re making the conversation harder, not easier.)

In terms of how to actually broach this conversation, pick a time where you’re both sober and can communicate clearly. Have the discussion before things have gotten too hot and heavy. Start with something like, “I care about sexual health, and I want to do this as safely as possible.” If you have something to disclose, you can say, “I need to disclose something about my health and give you time to think about it.” Share your boundaries as clearly as possible, and listen to theirs.

One last thing: If there’s a Planned Parenthood in your area, or assuming you’re a legal adult, a BDSM or swingers’ organization, you might consider asking for resources from people who want practice navigating these conversations. Something all three places—and others like them—have in common is that they’ll probably be able to give you a more nuanced idea of the incredible variety of ways people mitigate the risk of sexually transmittable infections. If you want to stay safe, this conversation is an essential first step, not something to get out of the way.

—Stoya