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How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!


Dear How to Do It,

I’m a woman in my late 20s and I’ve been with my boyfriend for two years. We are a good team—he is funny, affectionate, adorably shy and kind, and there is very little I would feel uncomfortable talking to him about. A year into our relationship, the day after his work’s holiday dinner, he confessed tearfully that he had drunkenly kissed someone. He didn’t work with her, and after some time and conversations, I decided that an immediately confessed drunken kiss with a stranger wasn’t that big a deal. I did ask him to meet with a psychologist, since it seemed quite out of character, which he did and has been ever since. We talk openly about monogamy and our limits and desires, and have decided to be with others only as a couple. About a year ago, we were hooking up regularly with an awesome woman—I enjoyed going out with her as well as having her over and appreciated her ability to talk candidly about sex. Though we met her on an app, I considered her a friend.

This past month I’ve been hit with an eye infection so bad I have literally cried blood. I’ve had eye problems in the past and am extremely paranoid about losing more vision. After three ER trips, lab results finally showed that I have chlamydia in my eye! I’m relieved because the correct antibiotics will hopefully solve it quickly. My partner and I were both tested around the start of our relationship two years ago and were negative. Aside from our friend with benefits, I haven’t been with anyone else since. I had absolutely zero doubts when my partner said he hadn’t either and full confidence that he would tell me if he had. But when I suggested texting our third, he got nervous and tried to talk me out of it. Finally, he acknowledged that when I’d been away for a month last summer, he’d seen that they were both at the same Pride event and gone to say hi and ended up drunkenly inviting her over. He didn’t tell me at the time (when he mentioned running into her, I asked if they’d hooked up!) out of embarrassment and disgust with himself.


He decided to commit to working on it in therapy, and since he felt it was his problem and not a reflection on our relationship, decided it was better never to tell me. He didn’t think about STIs because he used a condom (we always used condoms with her, and she was always very careful!) and because we’d hooked up with her in the past. Obviously, I feel betrayed, but a big part of me understands how it happened and why he chose not to tell me. But I’m also furious and filled with doubts, and also see a pattern of drunken semi-betrayals—are there more? I’m shocked he managed to keep this secret, as I’ve always thought him to be fairly bad at secrets. What other secrets are there? He feels horribly guilty and suggested couples counseling and blames himself for my bloody eyeball, though I don’t think that’s directly his fault. Oh, I love the guy and I really want to believe him. Am I being naive?

—Sickly Side-Eye

Dear Sickly Side-Eye,

It seems that genital and ocular chlamydia do correlate frequently—40–90 percent according to this article—so you should let your third know so she can get tested. You and your partner might want to explain what’s happened to your medical professional and ask if there are any extra tests, like throat swabs, they want to run.


You love this guy. It sounds like everything else is pretty great, and you’d like to keep dating him. Presuming that’s the case, take him up on the couples counseling and ask him to talk about his drinking and hookup habits with his one-on-one therapist as well. These therapists should be two different people. If you can afford it, you should consider seeing a therapist yourself to work through your doubts. Some of them sound pretty justified.

I don’t think you’re being naïve. You realize that two occurrences may be a pattern, and you’re aware that strong emotions can undermine judgement. Keep sight of your own needs. Think about where your limits are. If you’re one drink away from an anxious meltdown, let him know that cutting out alcohol temporarily will help you. If you need to go back to monogamy for a while, communicate that. Remember that you’re asking, and he does have the right to say no or negotiate. When something starts to feel OK again, talk about reintroducing it the same way you talked about opening up in the first place.


Dear How to Do It,

My wife and I have been married for a few years now and have recently started exploring a kink I’ve long harbored but rarely indulged. Specifically, I really enjoy hearing about her past experiences with previous lovers, often in great detail and often during oral or manual sex. I’m a very lucky man, and my wife has been more than willing to explore this with me. I do, however, want to remain respectful and not cross any boundaries. Is this a relatively common kink and, if so, do you have any best practices?

—Bedtime Stories


Dear Bedtime Stories,

There’s a whole, fairly busy subreddit that seems like it’d be right up your alley. Vicarphilia, which turned up in a search string, has few results and does not appear to have been studied. I’m not sure many would consider it a kink—I asked my lovers about their sexual experiences for years and few seemed to find it odd.

As for best practices, make sure to support your wife’s decisions. For instance, if she decides to stop the story, that’s her choice and you’ll respect it: No bargaining, pleading, or resentment. Yes, even if it’s during one of the hot parts. If you hear about something she doesn’t want to do again, no matter how enticing, accept her “no” as firm and final. She’ll let you know if anything changes.

Express your gratitude. Tell her how lucky you feel. Ask her if there’s anything you can do to cater to her sexual desires.


Dear How to Do It,

I’m a mid-20s, single straight man, and I work in the music industry. More specifically, I work in DIY music a lot, which is relevant because of the personal connections with collaborators that it necessitates, and the lack of institutions that mediate them. I work with quite a few women, and I find many of them attractive, and many of them are close personal friends as well as collaborators. A few years ago (while in college) I dated someone I’d been working with, and it was a pretty unhealthy relationship and ruined the collaboration before we even broke up. Mixing feelings with collaboration created a lot of stress on the relationship, felt like it raised the stakes of everything, and generally made both more difficult to navigate. The relationship also made my collaborations with other women much more complicated because my partner had some jealousy issues, and musical collaboration is a naturally emotionally potent thing.

Since then, I’ve decided that sex and romance with people I make music with should probably be off the table at least for now. I also feel that there is an ethical aspect to this: The music industry in general is a place with a lot of entrenched sexism, and that applies to DIY circles full of liberal arts graduates as well.


Adding sex to collaboration in this context seems like it’d have a ton of potential downsides for the women involved. (For example, I definitely don’t ever want people thinking that the way to get good treatment from me is to sleep with me, to say nothing of what might happen if a relationship ends badly.) I don’t mean to be saying that I should be making the women’s choice for them, it just seems easier to do the right thing if I just avoid sex and romance entirely. I’d also be weakening my own network if I made a habit of shooting my shot and missing with my collaborators. On the other hand, a lot of the people I’ve connected with most are the women I’ve made music with. I’ve had feelings for a couple of them since my last relationship (to the best of my knowledge, these feelings weren’t reciprocated). I made the decision to do my best to set them aside and continue just being friends and collaborators, which isn’t always the easiest thing.

It seems like if I don’t figure out a better way of handling things, me secretly having feelings for my friends/collaborators might be an ongoing theme of my life. Meanwhile, I’ve had a couple casual friends with benefits who aren’t musicians. These have been nice friendships and good sex, but I feel like these experiences have made me aware that I’d need to have being a musician in common with someone in order to have a romantic relationship with them (and that doing music together often leads to me having feelings for someone, even while our relationship remains platonic). Maybe I’m wrong about that, and I feel like I still have plenty of time to figure it out, but I do feel like I’m love-blocking myself at the moment. Any tips for not getting in my own way romance-wise, while steering clear of ruining friendships and collaborations, and making life even more difficult for women in DIY music?

—Out of Tune

Dear Out of Tune,


The best thing you can do here is not have sex with your co-workers. It leads to mess, there may be power imbalances like the ones you point out, and it can absolutely weaken your network of collaborators. Sometimes the right thing isn’t the fun thing, and I think this is one of those times.

People in other fields, on the other hand, may be more understanding than you may assume. Other entertainers will understand the hours, your relationship to the audience, and your dedication to work. Of course, you’ll likely have to tolerate the same from them.

Find a partner in a different field that’s close enough for them to get your grueling schedule but far enough away that you aren’t likely to work together.


Dear How to Do It,

I have been married about five months. Before we were married, my wife introduced me to her longest and closest friend and this friend’s boyfriend. She told me that her friend’s boyfriend had hit on her not long after he started dating her friend. My wife furthermore led me to believe she turned him down and informed him she would ignore it for the sake of her friend. Well, a month ago, I noticed texts to my wife where he was the one making plans concerning the four of us. Innocent enough she said, but I thought it odd that my wife wouldn’t be making these plans directly with her friend.

I started snooping on her phone, and while I don’t think anything is going on currently other than this cad being just a bit too friendly, I did find some sexting that took place between the two about two years ago (before I met her). She claims that there was never any physical contact with him, but I have a hard time believing that. Regardless, I now refuse to spend time with them, and I am also now feeling betrayed and having a hard time trusting her. Oh, by the way, she also has kept emails from previous lovers going back years. Should I confront her about these? How can I trust her anymore? Should I leave her? I just don’t see how I can ever trust her again.

—Trust Troubles


Dear Trust Troubles,

Why didn’t you trust your wife in the first place?

Yes, now we have to deal with your wife’s omission of the sexting and your feelings surrounding this. But we also have to deal with your snooping in her email and phone. So, what’s going on with you or your relationship that sent you digging?

I don’t think keeping emails, or even physical mementos, from previous lovers is odd or cause for alarm on its own. If she were keeping items out or in a high-traffic drawer in a shared home, or reading the emails regularly, that’d be one thing. But I feel like you would have mentioned any such behavior.


Whether you leave is ultimately your decision. Think about what you need in a partner. What kind of mental and emotional dedication do you require? How much of an in-the-present person do you need them to be? How much of their past can you tolerate? Then, simply assess how well your current partner matches those needs. There’s your answer.

—Stoya

More How to Do It

I’m a woman in my early 30s. I sometimes enjoy not wearing a bra in public (never in work settings, and nothing completely see-through, and my breasts are relatively small). I like both the possibility of somebody seeing my nipples through my shirt and the constant but minimal stimulation whatever shirt I’m wearing provides. Recently, on a solo road trip, I had the desire to pull my shirt up and expose my breasts while driving on the highway. I liked that somebody might see me, but realized that the chances of that happening were pretty minimal. Even though it was thrilling, I feel conflicted because I know if someone saw it could make them feel uncomfortable or violated. I’ve only done it the one time, but is this something I need to retire?