The Hook Up: Table manners and safer sex practices

What I was wondering was: How do you bring up the safe-sex question with one-night stands? Because society harks about using condoms, but it’s really not sexy to bring out the hospital-grade sanitary gloves or ask about potential STIs when in the midst of ripping the clothes off a virtual stranger. So how do you ask them without offending or ruining the moment?—Tired of Russian Roulette Sex

Anna says: That is an excellent question. When it comes to safer sex with new people, the rules apply to everyone equally, whether it’s a one-night stand, a friend, an ex, or an ex’s ex’s friend.

It’s not an easy topic to bring up, however, especially if it’s someone you’ve just met because who wants to talk about gonorrhea when her lips look like pillows and all you want to do is take a nap on them with your face.

Most people advocate having The Talk early on. If this is a one-night stand you’ve prearranged, then I admire your organizational prowess, and you can bring up safer sex well before it all goes down. If it’s not preplanned, then bring it up before things get too sexy, preferably before clothes come off (shoes do not count). To paraphrase you, it’s harder to have a civilized conversation when one’s skinny jeans are around one’s knees. Also because lust is a notoriously unreliable life strategy. It clouds our judgment and can cause us to compromise our values in ways we wouldn’t otherwise.

While talking about safer sex is a good idea, it doesn’t have to be a Big Deal. There’s no need to use a terminal illness voice. You want to please this person, right? And you want them to please you? It’s much easier to accomplish this feat using words (“Mmm” does not count). Most of the scripts I’ve come up with sound porny or cheesy, so you’ll probably have to improvise, but here are a few potentials anyway:

The sex boundaries angle. “Is there anything you don’t like / I should avoid?” And then after they tell you, you can talk about your own boundaries. If that includes using gloves with new partners, then say so. This addresses safer sex concerns AND helps you learn how to please each other better. Win-win.

The flattery angle. “I’m so stoked to be seeing you naked! That’s why it’s important to me to keep my sex partners healthy and hot. Let’s talk for a few minutes about statuses and the last time we were tested, and for what.”

The lighthearted/humorous angle. “You don’t want me to get pregnant, do you? Let’s talk about protection…”

The sexy angle. I can think of three scenarios off the top of my head to incorporate gloves in a fun, role-playing way. This doesn’t exactly get you off the hook from having The Talk, but if they’re into role playing, and you want to be safe in a creative way, it could work.

It’s helpful to have gloves handy (or whatever you’re comfortable using) so that you don’t have to stop and trek to the bathroom down the hall. Also helpful to remember is that no matter how awkward such a conversation may be in the moment, it’s far preferable to the one that goes, So I found this weird bump.” It’s your health and well-being, remember. Don’t feel like you should compromise that because “dental dam” is such an unsexy word.

As with most things, you’ll get better having this conversation the more you do it. And if any of your partners balk at having a safer sex conversation, or brush off your concerns, that is a pretty good litmus test about whether you want said person anywhere near your nether bits.

Good luck, Tired. I wish you all the sex!

Hailing from the rough-and-tumble deserts of southern Arizona, where one doesn’t have to bother with such trivialities as “coats” or “daylight savings time,” Anna Pulley is a freelance writer living in San Francisco. Find her at and on Twitter @annapulley. Send her your The Hook Up questions at

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