How to Do It

I Tried to Sleep With My Roommate’s Partner. Turns Out That Was a Mistake.

It nearly destroyed our relationship.

Man looking off to the side worried with a backdrop of angry and sad emojis.
Photo illustration by Slate. Photo by SIphotography/iStock/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,

I’m dealing with feelings of jealousy for the first time in about six years and I would like it to stop. For context, I have a roommate to whom I’m very close and we have some mutual attraction that we’ve agreed not to act on for a variety of reasons. They’re maybe my closest friend ever and I absolutely love them. The roommate is polyamorous and currently has three partners.

Advertisement

About two months ago I made a pretty major faux pas in asking out their partner M (who said yes) and it nearly destroyed my relationship with my roommate. I feel like their reaction was disproportionate, but I understood where they were coming from and we’ve worked through this and have been working on more clearly communicating boundaries. The basic essence is that Roommate doesn’t want their partners involved with each other, and while we’re not “partners” I’m included in that.

Advertisement
Advertisement
Advertisement

That said, we’re all involved in the local kink community and their partner W has gotten extremely good working with rope. The roommate has set W and M up to do rope stuff together, with other things occurring in the process. And this is where the jealousy comes in. Despite all other feelings involved, I’ve never felt jealous of Roommate’s relationships with people and I can’t imagine feeling jealous of M’s relationships with people… But I think I’m going to have feelings of jealousy over anything that happens between M and either of Roommate’s other two partners.

Advertisement
Advertisement

M and I have some solid chemistry and as I said, when I asked them out they said yes, so I know they’re interested in me. But I’m essentially not allowed to be anything other than casual friends with them because of Roommate’s boundaries. I guess I’m just feeling almost gatekept because of inconsistently applied boundaries. I’m also a little confused because me and Roommate aren’t romantic or sexual partners but they’re expecting me to stick to a boundary they usually reserve for those types of partners. A boundary they’re seemingly not enforcing with W.

Advertisement

How do I broach this conversation with Roommate without coming across as entitled or trying to be in their business about what they allow M and W to do together? I don’t want to influence how they manage their relationships; I just want a better understanding of why I’m facing this restriction meant for romantic partners when actual romantic partners aren’t having to deal with it.

Advertisement

—El Sueno Razon

Dear El Sueno Razon, 

The situation you’re in seems unbalanced. Do the same rules that your roommate has for you apply in the other direction? Has there ever been a situation where they were interested in someone who was close to you, and, if so, how was that handled?

Advertisement
Advertisement

You might start the conversation with curiosity: “It seems to me like M and W are having a sexual relationship, and you expressed to me that you didn’t want me having anything more than a casual friendship with M because you didn’t want your partners involved with each other. Am I missing something here?”

But, before you go into this conversation think about what your goal is. Is it their blessing to take M on a date? How about an explanation of where this double standard came from? Spend some time with yourself and figure out what you want out of the discussion. Also, think about what you’ll say if they refuse to engage or acknowledge that their policy is unevenly applied. Will you want to move out? Will you communicate that you’re no longer agreeing to their terms? Will you stay in the roommate relationship and continue to adhere to their expressed boundaries? All of this is up to you, and something that’s worth thinking about before you need to respond in the moment.

Advertisement
Advertisement
Advertisement
Advertisement

Choose your time wisely. You’ll want plenty of time to work through tough emotions in case they come up. You’ll want everyone’s biological needs to be taken care of—is the room too hot? Too cold? Is anyone hungry? Angry about something else and in need of some rest? You know yourself and your roommate well enough to understand what both of you need from the environment to stay present and engaged in a discussion. I think you’ve got this.

Dear How to Do It,

I find myself to be very physically sensitive to touch—easily tickled and easily startled, for example (there is no psychological or traumatic reason that I’m aware of). This means that I can’t tolerate slow or soft sex or teasing well. And my husband and I agree that “tolerant” is not how either of us wants to feel about sex acts. I’m happy with our fast-paced and rough sex life, but I can tell my husband would sometime like a different pace and a little more romance during the act. We once had a lot of success being intimate in a pool while we were house-sitting. Something about the all-over feel of the water made me more welcoming of a range of touch and sensation. Do you have any ideas of how we could replicate this when not underwater?

Advertisement
Advertisement
Advertisement

—Beached

Dear Beached,

I’m wondering if you’ve ever tried on latex, or any kind of boned corset. There’s a tight, squishing effect from each, and latex has the benefit of transmuting touch that might tickle if applied directly to skin into a spread-out sensation. If you haven’t experienced either of these kinds of garments, you might search to see if you have a store nearby that sells latex or corsets and try some things on to see how they feel. You typically can’t return these kinds of garments and they are expensive, so it’s worth a trek to experience them firsthand before purchasing. If you’re into that, but it isn’t quite enough, there’s a whole world of enclosure fetishism gear that can help you feel, well, enclosed.

Advertisement

Slow sex can be quite firm, so that’s an option, too. Instead of a feather-light touch, your partner can slowly move their hands across the broad parts of your back or hold other parts of you fairly intensely. You might make an evening of experimenting with different types of firm, slow touch.

And if you have a bathtub, that’s always an option. Sometimes, the obvious thing is what works.

Advertisement
Advertisement

Help us keep giving the advice you crave every week. Sign up for Slate Plus now.

Dear How to Do It,

My wife and I are exploring ethical monogamy. How we got to this point is a bit of a long story, but the spark of this decision came when, after nearly 25 years of marriage, I finally came to the realization that I am a trans woman (and also pansexual).

Advertisement

Here’s the complicating factor: We got married very young. We were deeply religious. Both virgins. The sum totality of my sexual experience is with her and her alone. Over the years, our own sexual relationship was extremely meek and mild. Sex has always been infrequent and very vanilla. It felt like we were minimally performing the sexual roles expected of us. I’m not interested in leaving my wife. Though it is still a work in progress, we feel that there are a lot of strengths to our marriage. Sex isn’t one of them. And so, while our marriage will continue to be a place of tenderness, support, love, and respect, we are exploring sex and romance outside of our marriage.

Advertisement
Advertisement
Advertisement

Now, as a 46-year-old nine months into my transition, I find the idea of forming new romantic and sexual relationships daunting. I know from transfemme friends that the dating scene isn’t always kind to trans women. When I add that to the anxiety of being a middle-aged person with very limited sexual experience trying to enter the brave new world of queer dating apps, it makes it very hard to put myself out there or know where to begin.

Advertisement

Transitioning is often likened to a second adolescence. That analogy fits me well because it not only describes the hormonal realities of my medical transition but also my experience of feeling clueless about my own sexual interests. I don’t know if I’m a top or a bottom. I don’t know if I’m into any kinks. Where do I start?

Advertisement

—Like a Virgin

Dear Like a Virgin, 

Take your time. Sexual understanding can be a beautiful journey. You’ve only recently discovered your gender identity and begun expressing it. You’re discovering who your femme self is. She might be a top. She might be a bottom. She might be a switch. She might not be into these kinds of roles at all. Don’t rush and relish the positive experiences you have.

Dating apps can be a nightmare. We’re basically ordering each other up like pizzas off of the internet, except without the delight of the Domino’s Tracker giving you updates: They’re getting in the shower. They’re grooming their genitals. They’re putting on clothes, getting on the train, and headed your way. When using them, put yourself out there succinctly and honestly. You can try adding “Transitioning woman newly exploring sexual expression” or a less specific “Excited to experiment and find out what I like” to your dating app bio so potential matches know who they’re swiping left or right on. Think of passes and unmatches as efficiency in action. You will absolutely get rejected, for unspecified reasons, for your gender expression, and for your marital status. Know that it’s nothing personal—you’re in a digital meat market—and move on with your life.

Advertisement
Advertisement
Advertisement
Advertisement

Safety concerns are another issue. Meet dates in a public place that you can easily and safely leave if you’re feeling uncomfortable. Make sure someone reliable has the name and face of the person you’re meeting, knows where you’re meeting, and when to expect you to check in. If you go to a second location, like their home or a hotel, send that trusted person your new address. Crucially, check in with them at the expected time. Keep your purse on you, and if a drink makes you feel funny, ditch it. Make sure you always know where the exit is. Try, despite all of these necessary concerns, to avoid paranoia and enjoy yourself. Consider self-defense classes.

Advertisement

You also might consider meeting potential partners in person. Queer community events are one place you could look, and you never know who you might meet at a social event like a book club or a potluck.

Did you write this or another letter we answered? Tell us what happened at howtodoit@slate.com.

Dear How to Do It, 

First off, let me acknowledge that this is a good problem to have. I can’t even ask my friends for their input because they’d all hate me. My wife wants me to sleep with other women. Sounds fun! But…how do I do that exactly? Backstory: My wife and I have been on a little sexual journey. At first, it started out small, just new positions, a little more sexting and flirting, but it escalated. We’ve talked about threesomes, group sex, things like that. I mostly assumed these were things that just got her aroused rather than things she wanted to make happen. It was kind of a fun game to play around with, fantasizing about situations that seemed implausible. But, out of nowhere, she told me I could have a hall pass. I didn’t even ask for it so I was kind of like “OK?” There are women I’ve fantasized about during our marriage but it was just daydreaming. But she’s committed. If I go out of the house alone, she tells me to let her know if I find any women to flirt with. I know that I get most turned on when my wife is turned on. She really wants this to happen. She hasn’t mentioned wanting her own hall pass, but that wouldn’t be an issue for me. I think it’s kind of hot too.

Advertisement
Advertisement
Advertisement

Anyway, the issue is obvious: How do I do this ethically? Sure, there are women I’ve met over the years I probably could have slept with but, “Hey! Just checking in, my wife gave me a hall pass,” isn’t really a compelling pickup line. I’m actually struggling to make my wife understand that I don’t want to pretend to be single, that crosses a line. What if I meet a woman who sleeps with me because she’s actually interested in me? But if I’m out hitting on women with a wedding ring on, I’m not going to be attractive. Instead, I’ll look like a scummy creep. And if I introduce myself like, “Hey! Nice to meet you! I’m married but my wife said it’s cool if we have sex,” I can imagine the response.

Advertisement

In any other scenario, I wouldn’t be sweating this, but she really wants this to happen and I get so turned on by her being turned on. I also don’t want to look a gift horse in the mouth. I just turned 40, I haven’t slept with someone else in 15 years.

—Confused Yet Horny

Advertisement
Advertisement

Dear Confused, 

Much like our previous letter writer, you’ll likely encounter some rejection due to your marital status. Again, think of this as efficient. Dating apps, the grinder of flesh that they are, might be useful to you. You can disclose your marital status upfront—as succinctly as possible—and people can swipe yes or no as they choose.

And I wouldn’t underestimate the appeal of messaging someone something along the lines of “My wife just gave me permission to have sex outside of our marriage, and my mind immediately went to you.” Make sure the situation is ethical—not someone who works for you, or you otherwise have power over—and put your desires out there. Be prepared for skepticism.

Advertisement
Advertisement

If there’s a swingers’ club or poly meetup in your area you also might attend with your wife for the purpose of finding interested partners. I encourage you to bring your wife for two reasons; single men are frequently unwelcome at these events to cut down on the circles of dudes staring with their dicks in their hands, and because I think she might find it hot to watch you flirt with women and maybe even pick one up.

—Stoya

More Advice

I started dating someone recently that I’ve really enjoyed connecting with and have found a higher level of chemistry with than anyone else I’ve dated. It’s exciting and has given me a chance to imagine a stable future with someone, something I’ve struggled to imagine in the past. But there’s something else that’s new for me this year that complicates things: I’ve started seeing sex workers.

Advertisement