Our advice columnists have heard it all over the years—so we’re diving into the How to Do It archives to share classic letters with our readers. Have a question? Send it to Stoya and Rich here. (It’s anonymous!)
Dear How to Do It,
I’m a 29-year-old woman with a 29-year-old straight male best friend who lives in another state. “Billy” and I became friends back in undergrad nearly 12 years ago. We clicked and just got each other. We had a falling out a few years later, but reconnected three years ago. We can read each other and are brutally honest with each other. Billy can get a bit protective of me and needy, especially when he visits, since we don’t get to see each other but a handful of times a year. I’m currently dating an early 30s man whom I’ve fallen for very quickly.
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We live about 90 minutes apart but spend every second we can together. However, I lied to him fairly early on. After telling him Billy was my best friend, he asked if Billy and I had previously had sex. I said no, but previously Billy and I had a friends-with-benefits period in undergrad that lasted three weeks. After we reconnected, which was as I was breaking up with a boyfriend, I used Billy as a rebound for a couple days. That was back in 2018. Nothing sexual has happened between him and me since.
Since I lied, my boyfriend has been caught looking through my messages on my phone and computer (they’re synced) twice. While initially super angry and feeling violated, I feel it’s allowed us to open and have good discussions about things. My boyfriend mentioned he didn’t like me telling Billy about our sex life (which I really have no position on). However, Billy now feels that my boyfriend doesn’t like that I have a male best friend and won’t like him when they finally meet.
I am madly in love with my boyfriend, and I love Billy; both Billy and I know a relationship between us would never work, even though our friendship does. Should I confess about having slept with Billy before and get that out of the way, so it doesn’t accidentally come out later and it’s a bigger deal? Should I not confess but take a step back with Billy and not be as close of friends? Or should I just not tell my boyfriend and maintain the current level of friendship with Billy?
—Looking in and Reflecting (L.I.A.R.)
Dear L.I.A.R,
I don’t think you should be dating a guy who looks through your cellphone. But you’ve decided to proceed, so here we are. Moving forward, yes, you should disclose your sexual history with Billy before your boyfriend finds out through a slip of the tongue or more snooping. You might want to practice beforehand what you’re going to say and think through different questions and reactions your boyfriend might have—this may be a deal-breaker for him. In addition, your boyfriend is private about his sex life, so if you want to continue dating him, you should curtail your sharing with Billy in that area.
I’m stuck on your suggestion of taking a step back with Billy. You describe Billy as your best friend and seem to deeply value that relationship. Your willingness to cool it with him to avoid correcting the record with your boyfriend gives me pause. I think it would serve you well to spend some time thinking through your feelings here.
—Jessica Stoya
From: I May Have Lied to My Boyfriend About My Real Relationship With My Best Friend. (May 25th, 2021).
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Dear How to Do It,
I’m a single trans man in his mid-20s. I’ve been on testosterone for about five years. Before I transitioned I lived as an out lesbian (and a gold-star one at that) with a few female partners over the years. I was never interested in men, other than perhaps jealousy from wanting to BE one when I got closer to figuring out my gender identity. However, after I began testosterone and started living as a man, I started to have fleeting thoughts here and there about men. The kicker is that for years, even as a lesbian, I would primarily watch gay porn. Something about primal sex between two men always turned me on. I know there is literature online about lesbians watching gay porn, and I’ve even seen some female-to-male forums discussing former lesbians, now trans men, developing an attraction to men.
About three or so years ago, I curiously ventured into the online gay hookup world and created a Grindr account. In that time, I’ve probably spoken with over a hundred men, all online, and never met up with one. I get off on sharing intimate photos back and forth. Even better if they send me snippets of them jerking off. Pretty much half the time I masturbate nowadays, I download all the apps where I have communicated with men anonymously (Kik, Snapchat, Grindr) and for the entire time I am pleasuring myself, I sext with various men. While I am jerking off, the idea of hooking up with a man excites me to no end. I talk a big game with these men too. But, literally as soon as I cum, I delete everything from my phone and am disgusted by the prospect of being with a man. I am just so confused by myself. Sometimes I think I’m bi, but the only time I want to be with a man is when I’m horny. Never do I see a man in public and think of him as attractive in the same way I do a woman. When I look to the future, I also picture myself dating women and settling down with one. I guess all this comes down to the main question: Do you think I am shamefully suppressing an attraction to men, or something else is going on? What is your arm-chair take on my sexting carousel when masturbating? I know telling someone what you think their sexuality is may be a fine line to walk, but I just really am at a loss for this habit I’ve developed.
— Confused
Dear Confused,
I think you are luxuriating in the liminal. One of my all-time favorite studies examined Craigslist cruising as a self-contained behavior, that is, an erotic event in itself regardless of whether actual sex resulted in these online interactions. The study found that self-identified heterosexual and bisexual respondents were more likely to find erotic the process of browsing sex ads on Craigslist, the posting of them, and the email exchanges than the gay men who answered. Though “success rate” of such exchanges (i.e. resulting sex) was measured in the survey, it was not the focus of the report. The authors Brandon Andrew Robinson and David A. Moskowitz surmised that “in seeking to explore and experiment instead of enacting their desires offline, bisexual and heterosexual men seeking men might find internet cruising and emailing to be an erotic tool for sexual self-expression, satisfaction, and possible identity development” outside of venues specifically designated for gay men. Additionally: “The anonymity and accessibility of the internet allows these men to find pleasure in cruising for other men without having to reveal their own identity, without actualizing ‘gay’ (i.e., physical sex with another man) behavior, and also without upsetting their potential partners or having sex outside of their relationship.”
So, the thrill of the act could arise from how near-yet-far it is to sexual contact with other men. Much has changed since the survey was conducted in 2008 (the paper wasn’t published till 2013). Craigslist no longer allows sex ads, and geolocation apps like Grindr seem to be the primary means that men coordinate sex with men virtually. However, it’s not unreasonable to interpret your cruising as similar to that of the respondents’, just with 13 years of technological process under your belt. Perhaps this is so erotic to you precisely because it is not actual sex with another man, nor does it ever have to be, precisely by your choosing. Or maybe this is a way of you exploring a side of yourself that is underdeveloped, as you suspect. Certainly, it is not at all uncommon to be repelled by your turn-ons in non-erotic contexts—the disgust response tends to diminish when we are engaged sexually. You seem to have a good grip on what you’re into and feeling, which makes me doubt that you’re repressing much here. I think you’re just feeling things out, and your sexting with men could just be one of those “it is what it is” situations. No biggie!
—Rich Juzwiak
From: I’ve Kept a Secret Sex Life From My Wife for Years. She’d Be Devastated to Learn the Truth. (September 26th, 2021).
Dear How to Do It,
Six months ago, my husband and I (25 years married) found a framework for our sex life that has allowed us to be, if not on the same page, then at least in the same story, sex-wise. I have come out as asexual, and he has realized that he has a special fetish (about which he previously has felt some shame). We have been able to follow the advice we found online and have certain interactions that are not sexual for me, but due to his fetish, very erotic for him. This is great, especially for him! We find one time per week for this non-sex sex, plus from time to time, I cuddle him while he masturbates.
In between, however, he talks a lot about sex, how attractive he finds me, how sexy it is if i do this or wear that, etc. I find this relentless focus on sex and on me disturbing and unsettling. I want to go about my business at home without having to relate to all this. I don’t want to wear certain things because he likes them and gets excited—except during our weekly session—and I don’t want to be praised if I happen to wear or do something he finds exciting or sexy. He feels he can’t be himself if he can’t talk about these things. He has agreed to try to control himself, but then he slips up and says them anyway. This goes for our non-sex sex sessions as well, by the way, where his “impulses” get the better of him and he does something that we have agreed he will not do (like “coincidentally” graze a body part). The conversations we have about this are very difficult and negative. I see that he is having more sex now than in the past many years, plus cuddling and attention and a general upswing in our relationship. He feels “constrained” and “jailed” (his words) and says I’m all boundaries and it’s so hard and he slips up because I have so many rules. He gets sad and depressed, and I feel that it is my fault even as I don’t know how we can proceed—or talk about these issues—without him feeling bad. He talks to a therapist but doesn’t want to go together. Can you help us with a perspective or angle that is more constructive?
—Too Many Rules
Dear TMR,
More constructive seems to be exactly what you’re missing. I reached out to Aubri Lancaster, a sex educator with a focus on asexuality and aromanticism, and she says you two “seem to be focused on what he wants more of and what she wants less of, which is not uncommon when a sexuality like ace is defined by what we don’t want.” So the first thing to know is that you’re not alone. An important question is whether your husband gives you platonic intimacy or if your intimacy together always has a sexual feeling to it. One thing you can do is think about what you do want—what does intimacy look like for you, and how can he give that to you. I think some balance in that area will be helpful, and asking for things feels more positive than a list of what you don’t want.
Lancaster also has thoughts on the difference between a boundary and a rule. She suggested a boundary is something an individual sets for themselves, and a rule is something set for other people. I don’t like your husband construing your boundaries—healthy, important limits we set to protect ourselves—as rules that limit him. You seem to want to stay in the relationship, so I’ll respect that, and suggest that you read her book recommendation Set Boundaries, Find Peace by Nedra Glover Tawwab. You might mark passages that feel useful to share with your husband, and ideally he’d read it himself and share sections with you as well.
You don’t mention a possibility of opening the relationship up, but even while remaining monogamous, your husband could talk to someone else—a trusted friend perhaps, or a support group—about his sexuality as an outlet to take some of the pressure off of you. He has a right to his desires, but he must find another outlet for them for your marriage to work. We’re still undoing the idea that everybody wants sex, and that sex needs to be a part of every long-term partnership. Your boundaries, no matter how much your husband resents and invades them, are valid.
—J.S.
From: My New Guy Won’t Do What I Actually Want During Sex. I Know a Real Man Would.(November 30th, 2021).
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