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 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. 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.)
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.
Dear How to Do It,
After 10-plus years in a monogamous, mostly stale marriage, I (a 42-year-old woman) am separated and hoping to have amazing sex again. For me, that means returning to the kinky, D/s sex I used to enjoy. I’m not looking to date or have casual sex with vanilla partners. Recently, I’ve been chatting with a dominant man I met on a kink site, and we’d like to get together in-person. We have had frank discussions about expectations, limits, and mutual respect. But I don’t know the first thing about navigating a hookup with someone I met online.
To start, we are anonymous—no names, phone numbers, or other details. It’s sort of a “don’t ask, don’t tell” situation, and I’m OK with that. I’ve seen several face pics and chat with him often enough to feel he’s likely trustworthy. But am I crazy to consider meeting up with a man who won’t tell me his name? How can I keep myself safe if I don’t want to tell anyone where I am, what I’m doing, or who I’m with?
He also lives about five hours away, so we can’t get together first for a “prescreening.” If we arrange to meet, it’s with the intention of having D/s sex. Where and how should we do that? Do I just give him the details of my hotel room and hope for the best? What about STIs or the potential that he’s married and has a partner who might try coming after me? What level of transparency should I demand? I’d really like to make this happen, but I clearly have no idea about the rules of the game.
—Kinky but Cautious
Dear Kinky but Cautious,
This is unsafe. Anonymous encounters are inherently dangerous. It is completely reckless to meet up with a stranger in a hotel room five hours away from your support system for submissive BDSM play—especially since you don’t want to tell anyone where you are, what you’re doing, or who you’re with. There are numerous ways this could go very wrong, some of which you identify in your letter. There are no ways to ensure your safety in this situation, and I strongly encourage you not to meet up with him.
Ten years is a long time to live in a stale marriage, and I imagine you’re excited to engage in a fulfilling sexual interaction, but this is not the one. Keep swiping till you find someone who is—at minimum—willing to give you some background information and travel to your area for an in-person prescreening talk.
Dear How to Do It,
I’m a divorced mom, and I recently started dating. I love being on the apps and have made some great matches. A couple of these got very sexy very fast, and there have been some scorching-hot text exchanges with one guy in particular. I don’t send nudes, and I don’t send any compromising photos that show my face (the photos I do send are pretty tame anyway—just underwear shots). But I love sexting and am a very eager participant in these conversations.
But I feel very, very ashamed and guilty about these conversations. I know intellectually that we are all consenting adults, and that there is absolutely nothing wrong with what we’re doing, but I cannot shake the bad feelings. Some part of this surely relates to my work—my job entails preventing and responding to incidents of sexual harassment and assault, so I spend all day every day thinking about all the worst-case scenarios. And some part is clearly how women are socialized to think: Even though my parents were pretty liberal, negative societal messages about female sexuality still clearly affect how I think. And I’m mildly kinky, which is also a source of deep embarrassment that I’m just now starting to overcome, and that makes me feel even worse.
So what do I do? I love these conversations and get very turned on by them, but the negative feelings swirl in the background and keep me from fully enjoying myself.
Dear Secret Sexter,
You’ve got a broad-strokes idea of what’s going on for you emotionally—some part surely relates to your work, some part is clearly socialization—and I’m wondering if further detail and clarity around that might help. The next time you’re having these negative feelings, listen to them. If there’s fear, what is the fear of? If you’re feeling self-judgment, what exactly are you judging? With a more granular understanding, the hope is that you’ll be better able to think through the tension between your intellect and your emotions.
For instance, worst-case scenarios. What are all the worst-case scenarios, what can you do to mitigate each, and is there anything you can do but aren’t already doing? Either knowing you’re doing everything you can or implementing the missing strategies and then having that knowledge seems like it would help. Recurring messages about female socialization can be an opportunity to compare these internalized rules with our own beliefs.
You might find that practice helps on its own, too. Exposure to discomfort can increase our ability to tolerate it, and there’s something about successfully doing the thing we’re afraid of that decreases fear.
Dear How to Do It,
I am a cis woman and in my mid-40s. I have never been in a relationship, and I’ve only had one sexual relationship, which was a short-term friends-with-benefits situation over 10 years ago. Since I was a teen, I thought I’d have a meet cute, and that’s how I’d meet a partner. That never materialized, so I tried a few dating apps over the years, which were disappointing.
Fortunately, I have a satisfying and enjoyable masturbation life. I’ve worked through a lot of my baggage in recent years and discovered how overwhelmingly sensitive I have been to the concepts of patriarchy, toxic masculinity, and fear of sexual assault. On top of that, almost all my girlfriends and female family members have married men that make me ask myself, “Is that institution worth it for me?” I have always been attracted to men and considered myself heterosexual, but at this stage in the game, I don’t know that I have it in me to try to find that needle-in-the-haystack renaissance man. I have had “girl crushes” about women I find attractive, and I joked with a friend recently that I was ready to be pansexual, bisexual, or lesbian if it meant I could find a companion, and I’ve started imagining sex with a woman. I wouldn’t even know where to start to dating women when I’ve never really dated before at all! At this point, I feel like my sexuality is more fluid than ever, and I’m seeking an intellectual, emotionally intelligent human with a wicked sense of humor. I feel alone in this predicament, and while I love myself and think I’m pretty amazing, I can see how I would look weird from the outside to any potential partners. What do I do?
Dear Le Sigh,
I hear from people in their 40s or older who are newly exploring some facet—or the whole—of their sexuality at least a couple of times a year. Many people consider sexuality and gender to be fluid, in the shape of a spectrum or even constellation. And political lesbianism (not that that’s necessarily what you’re describing) has been around since the ’60s. It’s unlikely that someone out there has had near exactly your life, but there are perspectives out there with overlap that you can look to for insight.
Dating, whether we’re doing it for the first time, the first time in a while, or the 500th this year, is a process of getting to know someone. Sure, there’s the assumption that we’re looking for long-term companionship, sexual interaction, or both, but in the process of evaluating whether we’re a match for either we’re getting to know each other, which is something I think you’ve already got some idea of how to do. And when you describe what you’re looking for, it’s all personality—which is great, and an indication that you’re looking for a significant intangible connection.
Sexual experience does tend to confer a certain ease in experimenting with a partner’s body, communicating what feels good, and general technique. But each new partner means learning a person’s sexual response anew. And hormonal fluctuations, context, and the progress of time may all change an individual’s response and desire. You’ve probably seen this in your own body—different things feel good at different times. To figure out where to start, think about what feels good for you and err on the side of teasing or being gentle.
As for the perceptions of others, try to remember the plurality of that. Someone, somewhere, maybe even reading this right now, is going to think you’re weird. Someone else is going to think you’re brilliant and delight in your quirks. I’m hoping they’re somewhere near you.
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?