I’m Dying to Have a Threesome With Two Men. Why Does Every Attempt Fall Apart in the Same Way?

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

Dear How to Do It, 

I’m (35F) very interested in having a threesome and have been working the apps to try to find the right person to help make this happen. I’ve had a few bites. I was sexting with one guy for days on end about our joint fantasy of making this happen, and I found a second guy, who said he’d like to join us. But then, when I tried to get ahold of the first one, poof! He vanished. And this is not the first time this has happened. It seems like, most times, when I try to actually nail down a date for meeting up at a bar, etc. to see where it can lead, the guys just don’t follow through, which makes absolutely no sense! They obviously want this to happen too. Is there something wrong with my approach (sexting, then gauging interest)? Is it normal to go through a million duds before it finally comes true? For some reason, I thought making this happen would be easier, and I could use some guidance.

—Pipe Dream

Dear Pipe Dream,

Coordinating a threesome among strangers can be a challenge even for active queer guys—so much so that some apps and hookup sites like Sniffies have baked-in options for coordinating groups, orgies, and gangbangs, clearly speaking to the general hassle of pulling this off. Just as adding a third body to your bed can expand the sexual possibilities seemingly infinitely, so does it potentially involve that many more issues and roadblocks. You have to find two people who A) are into you, B) are into (or at least willing to tolerate the presence of) each other, and C) both won’t flake. It’s so tough to coordinate that it makes obtaining a liquor license seem like a snap.

One thing you can do is determine if the apps you’re using to set up these three-way dead ends have a group chat option—that way, everyone is in communication with everyone and you aren’t doing all of the hinge work. (Feeld has this. I’m not saying this because we’re getting paid to hawk Feeld—we aren’t—I just happen to use it and have noticed.) Anecdotally, the most luck I’ve had coordinating this stuff is with a boyfriend or fuck bud: It simplifies the planning if you already have somebody you can count on for sex. Then only one person in the equation, instead of two, has the kind of lack of interest that makes flaking so easy. And, yes, it’s common to go through duds before this actually happens. As always, patience is crucial.

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Dear How to Do It, 

Over the past few years, I have experienced numerous traumas, from health and work issues to friendship and relationship breakups to having numerous people I know dying, getting cancer, etc. There was even a murder-suicide in my extended family! I have been in therapy for all this stuff and have tried a pharmacy’s worth of meds, all of which exacerbated my health issues and caused me to gain weight.

So now I’m in my early 40s, feeling rotten about my life, my looks, my health. I’m employed, but I don’t have a career. I have no savings and a reasonable amount of debt, all of it medical and student loans. I struggle to exercise, as most vigorous activity makes me nauseated, and I’m currently recovering from a minor surgery. I was always fairly fit before all this crap started raining down on me, but with the breakups, health issues, and weight gain, my confidence has taken a steep dive. And I just feel so alone.

I’m trying to figure out how to both build a community (with friends who will reach out to me, especially when my depression makes it more difficult for me to reach out) and meet partners, at a time when I feel as if I’m not wanted anywhere.

I’m a queer man who came of age during the height of the AIDS crisis, and my anxiety has kept me from no-strings-attached hookups. I simply never developed a taste for anonymous or even casual sex. I just need to get to know someone a bit more before I feel comfortable enough to hook up. Also, I don’t drink, which otherwise might both lower my inhibitions and put me in bars, where other queer fellas hang out. I’m in a fairly liberal large city, on a dozen dating apps, and having very little luck.

For the more dating-and-relationship-based apps, I’m not getting matches or messages. On the more, shall we say, location-based apps, the very few messages I get are just “Hey” and “How are you doing?” Those are fine openers, I guess, but these guys don’t seem to try beyond that or are literally half my age (which feels creepy to me, as I’m not into daddy-type play). I have had exactly zero offers of dates. Obviously, I’m not leading with “I’m super depressed and hate my life,” but something must be wrong.

I get that as a short, fat middle-aged teetotaler, I’m not everyone’s cup of tea. (I know I’m not mine!) But I’m funny, charming, kind, and responsive, and I’m not bringing up any of the traumas or depression in my profiles or messages. So, what gives? How do I find people who will bother to make some effort, when it takes so much effort just for me to get out of bed?

—Fat, 40, and Friendless

Dear Fat, 40, and Friendless,

Your letter is, on one hand, a downer but, on the other, full of hope. Let’s focus on the latter aspect, as it will pull you through. I love that, despite your feeling “rotten” about your life and expressing that it takes effort for you to get out of bed, you got out of that bed and wrote this letter. You’re actively looking for partners. It’s thus far been fruitless—but that doesn’t mean that you need to give up. Keep going. Keep those profiles up. Even if it takes you weeks or months to get a nibble, a nibble isn’t nothing. You aren’t willing to give up on yourself, so don’t.

You can, however, expand your opportunities. Since you’re in a fairly large, liberal city, there must be an LGBTQ+ center near you. Find it, take note of the calendar, and start attending activities. Allowing people to see you in person may impart your humor, charm, kindness, and responsiveness more effectively than apps can. You should also look into local speed dating, whether via the center or other organizers. This may remain a frustrating and slow-moving process, so stay patient. Tons of people feel the way that you do, and so many people find love when they previously thought it was hopeless.

I want to also encourage you to look into nonvigorous activity. Think walking, yoga, and light weights. This stuff won’t necessarily melt away pounds, but it may give you a good physical foundation for you to possibly transition to more challenging activity. I’m recommending this primarily for the reason that I always recommend exercise in this column: It’s good for your mental health. Your self-image isn’t torpedoing all efforts to connect, which is great, but the better you feel about yourself, the more you may want to share that self with others. Seeing progress in any form when it comes to fitness—even adopting and executing a regular regimen counts as progress—has the potential to bloom your hope from the seedling that it is now. Give it a shot.

Dear How to Do It, 

I’m bi and in a monogamous happy relationship with someone who absolutely would rather break up than open up our relationship. I’ve always been in closed relationships before. We’re 28 and serious, talking about marriage and kids. And I just had a solo two-hour crying jag—one of several over the past year that has snuck up on me without warning—about never getting to have sex with a woman again. Should I be listening to this part of myself? If so, how? I know that my partner would be insulted and hurt if I brought this up, because just hinting at opening up led to spiraling last year.

—Confused

Dear Confused ,

Here’s what you’re betting will happen if you don’t listen to this part of yourself: The voice telling you that you want to experience women/perhaps some form of nonmonogamy will stay at a low, manageable pitch. The hope is that the hunger will remain tolerable and not turn into starvation. I’m calling it a bet for a reason, as there is no guarantee of this; it’s merely the hope you’re organizing your romantic life around.

I can tell you that I was in a similar position around your age—probably even earlier. I started thinking, Wow, I’ve signed on to have sex with no guy other than my boyfriend for the rest of my life. I found the idea increasingly suffocating and, in my early 30s, crapped out. It wasn’t “too late.” (I don’t think it’s ever too late to trade an unsatisfying life for one that suits you better.) But I did spend a lot of time in a relationship that I knew, deep down, wasn’t tenable. If you choose to stay with your partner, you’re also betting on the happiness of the relationship remaining bigger than your desire for others (and, in your case, a gender-specific pool of potential partners). That’s certainly possible, but you should ask yourself if it’s probable.

Do you leave the happy relationship for something far less certain, something that also doesn’t guarantee sexual satisfaction? It’s a tough call. Perhaps to aid in your decision, you should evaluate your communication with your current partner. This desire to have sex with women is a part of you, something that has been affecting you profoundly and spontaneously. You can’t talk about it with your partner because of their sensitivity issues, so this is something that you’re expected to suppress to the extent that it cannot be spoken about. That seems like a rough way to live the rest of your life, and you’re young. If you have no outlet at all, don’t be surprised if these crying jags continue. It can be hard to leave a relationship that is overall pretty good out of fear of loneliness. But if your partner remains impossible to communicate with on this matter, you will be dealing with it alone—just as you would if you broke up.

Dear How to Do It, 

I have had almost a dozen miscarriages, and we have tried all medical options available (including surrogacy). Due to reasons beyond the scope of this inquiry (age, finances, etc.), we are done. My husband has a child from a previous marriage. I have PTSD from the fertility things done to my body (diagnosed four years ago), postpartum depression (turns out you can get that even when you miscarry in the first trimester), and the general struggles of living in a world where all my friends and work colleagues are parenting kids the ages of the children whom I desperately hoped (and bled, and sweat, and paid out the nose) for. My husband has said multiple times that he needs sex at least once a week. His cheating ex-wife gave him sex only once a week. I think I would be more open if he didn’t grab at me (albeit in the ways that I have indicated work best) when we are pushing up against that one-week mark or if his mood wasn’t pegged to regular sex. I know he will be a lot kinder if I have sex with him, but my body just doesn’t want it on demand. How do we navigate this?

—Am I a Fleshlight?

Dear Fleshlight,

What sticks out to me here is this line: “I think I would be more open if he didn’t grab at me (albeit in the ways that I have indicated work best) when we are pushing up against that one-week mark or if his mood wasn’t pegged to regular sex.” Don’t be afraid to revise an earlier request—if something that you previously indicated will work for you turns out to not, that’s OK. We are all feeling our way through life, and compassionate partners allow for process, which may involve changing our minds and/or rerouting. Ask him to try something else when he wants to initiate physical intimacy, perhaps involving words and not hands. You should also discuss the way he displays his seventh-day moods. You can’t ask him to change his feelings, but he should know that if he gets pouty or petulant when he hasn’t gotten any in a while, it’s also doing his cause no favors.

Finally, you should be patient with yourself. You’ve been through a lot. Your postpartum depression should decline as time goes on. There are therapists who specialize in infertility. Seeing one may provide you with tools to help manage your PTSD and general feelings about your ordeal. It’s hardly surprising that you’re having issues with sex given all that, and it’s on your husband to be supportive and understanding.

—Rich

More Advice From Slate

My husband and I have been married for going on seven years. When we married, he knew I was bi, but I had basically tucked that away to end up with the man of my dreams and choose the P over the V. But we’ve been talking about and considering a threesome with another woman for a few years, but just recently started to set it up. A friend of ours is a swinger, and she hooked us up with a girlfriend of hers. Since then, we have taken it slow. She and I had dinner and drinks to discuss. Then she came over for drinks with my husband and with me. The night ended all together, back at home, continuing to discuss and trying a kiss. Negotiations were going really well—until I realized that, for our first time in a threesome, I’m not comfortable with my husband penetrating her with his penis. He is upset with me for putting this boundary on the table. I don’t think I’m being unreasonable here. Am I?