How to Do It

My Boyfriend’s Obsession With His Straight “Friend” Is Out of Control

A man stares at another man, with a grimace emoji.
Photo illustration by Slate. Photos by Getty Images Plus.

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,

My boyfriend of just under a year, “Tom” is pansexual, which has never been a problem (I’m a straight woman, FYI). However, the night we met he told me that he had recently hooked up with a straight male friend, “Brandon,” and then been rejected, and this situation in particular is an issue. It is obvious that Tom has a huge crush on Brandon. Tom has said on a few occasions that he was ready to come out to his religious parents for Brandon and was hoping to be his boyfriend, but Brandon told him that the sex was a one-time thing and asked him not to tell anyone (a request which he obviously did not honor). Instead of backing off, Tom will text Brandon to join our group at any outing unless I expressly ask him not to by saying that I would like tonight to be just us, or that our friends have invited only us out. When Tom does invite Brandon places, Brandon often does not respond or responds hours later vaguely. Once, Tom said that he wanted to use my phone to call Brandon because he thought he’d actually get him to pick up by using a number not his own that Brandon didn’t recognize. If we pass a bar that Brandon is known to frequent regularly, Tom likes to stop in to see if he’s there, and will want to hang out if Brandon is there. He also repeatedly violates Brandon’s request to keep their hook up under wraps. He’s told many people, not just me. The one time he did get Brandon to hang out, Tom pissed me off by staying out hours after he told me he was coming back, letting his phone die so that I couldn’t reach him, and then waking me up at 3:30 in the morning to let him in because he didn’t have his keys. He’s also lately been floating the idea of Brandon joining us in a threesome, because I have expressed interest in us finding a male partner for one and wants me to spend one on one time with Brandon as a start to getting him home with us. At this point, I think I’m about ready to throw in the towel and let Tom chase this man and implode their friendship unencumbered by a relationship with me. What do you think?

—Brandon Blues

Dear BB,

It does indeed seem like it’s time to throw in the towel. Fleeting distraction that comes from what some in the poly world call “new relationship energy” (or NRE) is one thing, but it seems that Tom’s infatuation with Brandon has spanned your entire relationship with him and it’s not getting better. He’s only been distracted for the duration of your time together. And then there’s the badgering, the refusing to take a hint, the let-me-use-your-phone-to-call-this-guy-who-won’t-pick-up-when-I-call, the violation of Brandon’s trust. All red flags that would inspire me to question not merely the viability of the relationship, but Tom’s character. He’s foisting himself upon someone who is clearly not interested, despite having someone who is: you. And now he’s trying to rope you in to his unceasing mission to get Brandon back in his bed? Hell no, forget it.

But then, you’ve given me nothing to work with in Tom’s favor. While I understand that you may have edited for brevity, it’s telling all the same that you have little to say of Tom’s direct treatment of you or what’s good about your relationship with him. Try making a list of those things to yourself right now, and if you can’t, well, that’s even more proof that your coupling is doomed. I have to assume that in casting your question the way that you did, you are essentially asking for a co-sign on an already-determined decision to end your relationship. Well: Co-sign.

Dear How to Do It,

I keep having really intense fantasies, and I think they are a problem that needs to stop. Some context: When I was a child, my father sexually abused my sister, and she took it out on me. I didn’t find out about my father’s abuse for years, and growing up I never questioned my sister’s behavior because I took that as normal. My sister needed me to be a “good” man to contrast my father’s bad man, but if I didn’t live up to her ideal image, she would scream and curse at me. Eventually, I started living for myself and trying to be a better version of the me I am, instead of the me my sister wants me to be. And I feel much happier and healthier for it.

But I keep having these really intense fantasies about “bad girls,” the kind of girls my sister calls sluts and whores and wouldn’t let me be friends with growing up. Like, she’s everything my sister hates in women, but she’s kind and I feel safe with her. She doesn’t always take the lead during sex, but she gives me positive reinforcement and I can be as passionate as I want. But I know that sometimes a “bad girl” can really just be a shitty person. My previous attempts at dating have only put me in repeats of my relationship to my sister. And the me that I am is still a goody-two-shoes nerd. I genuinely don’t enjoy activities you associate with “bad girls” like clubbing or drinking. And as a man, I know my nervousness around sex and kissing and stuff isn’t attractive, especially now that I’m 25. My heart says that a bad-girl-good-boy relationship would make me happy. But my head keeps telling me that such a relationship is unfeasible, and I have to stop having these fantasies. I thought, as people more familiar with “bad girls,” you all could give an informed second opinion on the matter.

—Good Boy

Dear Good Boy,

Let’s put aside any moral judgement on your fantasies and desires, which I think your anxiety suggests are beyond your control, as they are for many people. The problem that I see here is of expectation: It’s one thing to fantasize; it’s another thing to believe the inventions of your own mind (in this case, clearly influenced by your sister’s mistreatment of you). I don’t want to tell you it is impossible to find a woman who identifies as a “bad girl” because she enjoys sex, alcohol, and going to clubs, but I know a lot of women who enjoy those things and don’t subscribe to that identity or, in fact, consider their behavior “bad.” I understand from straight porn and Fiona Apple that “I’ve been a bad, bad girl” is something someone might say to titillate, but there is more to a partner than dirty talk and pop-song lyrics. Unless you find a domme or someone committed to doing as many crimes as humanly possible, I don’t believe you’ll have any ease in finding a full-time “bad girl.” I think this one-dimension notion of a partner will inhibit connection. Just try finding a girl first. You say you feel happier and healthier now that you’re living for yourself, trying to be a better you for you and not your sister. Well, don’t impose the same restrictions on other people that you found necessary to liberate yourself from. You know better than that.

Dear How to Do It,

I am a 56-year-old man married for 26 years to a wonderful woman. We have had our ups and downs, but as we hit middle age, we experienced a renaissance in our marriage sparked by sexual awakenings. My wife admitted that she has always been bisexual, and actually dated women in college. She had never told me this before. I always had felt like I wasn’t enough, and that moment was oddly liberating for me and for her and especially for us as a couple. We worked in therapy and came to an agreement that she could date and sleep with women separate from me. I still support this, because I see how it helps her experience her complete self.

As for my fantasies and desires: I put them on the backburner because they are out of bounds. I find myself wanting to go on dates with other women. Honestly, it’s not really about sex or physicality. I have issues with erectile dysfunction, and sex feels like so much pressure anyway. For me, it’s about capturing that feeling of being desired and wanted by someone new, and the enjoyment of expressing that feeling to someone else. Getting dressed up. Going out. Butterflies. Nerves. And the enjoyment. The spark or connection.

This isn’t something I’ve had with my wife in awhile. We make great life partners and are committed to each other. She has been able to explore and feel the energy she desires both sexually and interpersonally. I’d like to revisit the boundaries with her, but I fear she will think this is about sex. It’s not. I’ve had to work hard to process jealousy and any feelings of inadequacy that I’m not enough for her. She as told me she is thankful and grateful, and doesn’t see how I do it. It isn’t easy. But it’s important to her and to me, so it’s worth the work. But she doesn’t seem willing to do it for me. I feel like she’s basically saying she’s not capable of this. I also don’t want this to feel like an ultimatum when we do talk about it. What’s a good way to approach this?

—Interested in Illinois

Dear Interested in Illinois,

Your craving for newness is completely understandable and quite common. This feeling is something that a partner of more than 25 years is, by definition, incapable of providing in its raw form, so craving it does not necessarily indicate inadequacy on your wife’s part. But have you actually raised this with her, directly? Your wife “doesn’t seem willing” to allow you the same freedom that you have to her, and you “feel like” she’s “basically” saying she won’t be able to do so. Instead of reading into a cliché that itself bespeaks a lack of rigorous engagement (“I don’t know how you do it”), it’s high time for a direct discussion. Perhaps illustrating how you do it would be a useful in: Through your recounting, you can show her how, despite your intial misgivings and the considerable work involved, you were able to get to a place where you don’t feel threatened by her desires that extend beyond your capability. Explain your process. Show her how the sausage is made. If you don’t want her to think that your interest in dating other women has anything to do with sex, explain that up front. Tell her that while you remain committed to her as a life partner, you have your own itch that a partner just can’t scratch. Given how the nature of your and her desires diverge considerably and present differently, she may push back, so you should choose your words carefully and provide plenty of reassurance and compassion. Let her take her time processing your request and, depending on her comfort levels, maintain it as an ongoing conversation without the expectation that your arrangement will change after just one talk. What you wish for is something that a lot of people do (many of them identify as poly), and it’s also something they’re able to explore without detriment to their primary relationship. I think the main thing to do is to make clear that this is not your way of dog-whistling discontent or an evaluation of what you have with your wife, but desires that extend beyond the realm of your relationship and that, ideally, will stay there, even if you’re given the green light to pursue them.

Dear How to Do It,

I have been casually seeing a guy for almost a year. We do relationship-y stuff and we genuinely care about each other, but no one is pushing for more. We’re both in our late 30s with kids, so the current setup works.

What doesn’t work is the sex. I mean, it’s good, but I’m looking for great. It starts out really hot and he gets me going, but once he’s inside me, he always comes too fast. Three pumps and it’s over. I have the best orgasms when I’m being penetrated, so this is big for me. I’ve also never have never had this issue with someone I actually care about. I feel like it’s something that we could work on, but he gets very embarrassed when I bring it up. And he is very concerned that I’m not satisfied, so he tries harder to make me come orally and digitally, but it’s like he’s rushing to get me to come because he can’t hold it. I’m not afraid to have the conversation again, but I’d like to offer suggestions or try some things that could help instead of just airing my frustration … and so far Googling has given me nothing.

—Extended Release

Dear Extended Release,

A few things to try: ED drugs (especially in guys who come as fast as possible for fear of losing their erection), a topical aenstethic to desensitize the penis, pelvic floor exercises (useful not just in a PVC-muscle-toning sort of way, but also some report the ability to help them last longer when performed during sex), and the so-called “pause-squeeze” techique where your parter, upon nearing orgasm, withdraws his penis and either you or him sequeeze where the head meets the shaft until the feeling of imminent ejaculation subsides. I think you should also just ask him to slow down in general—I know things can get fraught in the moment when one partner is desperate to satisfy the other, but he’s tripping over his own dick here and demonstrating the ineffectiveness of his methodology as he exercises it.

Good for you for not being afraid to talk about this stuff. Keep it up—let him know that you have faith in his ability to work through this and that your ability to share a satisfying sex life with him. Your confidence may rub off on him, proving utterly essential.


More How to Do It

My husband and I have been together for two years. Just married nine months ago now. I noticed that he was being distant from me, and also that he was constantly hiding his phone. Every time he would go to bathroom, he was always keeping the volume on vibration, always face down. He never put it down. One day, he wasn’t feeling good and he left his phone on the bed, so I picked it up to plug it in the wall charger. My gut told me to check it, so I did. In his Google search history, I found several different times he Googled Pornhub. I lost it, of course.