How to Do It

I Have an Intense Crush on My Couple Friends. I’m Not Sure What to Do Next.

This has gone terribly in the past.

Someone writing a long letter.
Photo illustration by Slate. Photo by araelf/iStock/Getty Images Plus.

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 have a crush on a couple. I didn’t realize they were together at first, partially because I don’t make assumptions about people’s sex lives and partially because they each have their own independent je ne sais quoi.

While I am bisexual, being conditioned as straight led me to identify that I had a light crush on the man, initially. However, I have dreams about cuddling and kissing the lady in the relationship. I have no desire for ill-gotten gains; meaning, I have no desire for one over the other, and I don’t really want to be a throuple or equal in their relationship. I just want a healthy friendship with some bonus play on the side. Basically, I don’t want to subtract from the relationship only add, and I certainly don’t want to complicate the lovely dynamic they seem to already have with each other.

They once brought me home with them after a late night at the bar, and while I was onto the possibilities, drama in the way threesomes have previously gone down and the fact that I was drunk led me to behave like I was a little clueless or had lost the plot, even though I hadn’t. The reality was that I just wanted the lady to acknowledge or verbally consent as to what was going on before I made assumptions or acted.

I’ve had women in the past become jealous of how I interacted with their man or mostly how their men behaved with me, or state that I can’t touch them because they are not into women, among other gaffes, each of which resulted in the loss of the friendships at play. I would like her to know I was on her side first and foremost. I’m not even sure she is aware I’m crushing on her but I do think she is aware I am at the very least attracted to her man. (Based on the conversations, I already knew the guy was down, if not already plotting the possibility of a tryst). I know she has been with women in the past, and this isn’t my first threesome or dalliance with women, but it is the first one where I want some cards on the table, so no confusion, insecurity, or miscommunication will derail the entire process and friendships.

I fear/dread initiating this conversation so I’m wondering if there are there any scripts you could suggest, or ways to lightly imply that I dig this duo and would enjoy a threesome and have them engage with me on it? I thought about writing the Lady a light love letter suggesting as much, as I want to establish ground rules with her, as I see my role as subordinate to her but I’m undyingly curious to hear your thoughts and opinions on how to proceed.

—Elated By a Lady and her J

Jessica Stoya: Did I just read Lady Chatterley’s Lover?

Rich Juzwiak: Is that what the plot is?

Jessica: It’s been so long.

Rich: I’ve never read it.

Jessica: The kind of feverish, breathlessness behind this letter is what made me think of it.

Rich: Married, feverish, breathless. I think that the suggestion here for getting across that our letter writer is interested in the woman can really be as easy as flirting with her, telling her that she’s beautiful, and all of a sudden paying more attention to her. Because if somebody’s already attuned to that—if you start saying things along those lines—people are going to pick up on that easily. I understand the desire to tread lightly here. All of that makes sense, especially because friendships ended as a result of this kind of thing before. But you’ve been cruising along with these people for this long, you can have the patience and start to talk about how hot she is, let’s say.

Jessica: Agreed, and also, you’re risking the friendship every time.

Rich: Yes, you’re right. That’s fundamental. You never know what’s going to happen.

Jessica: Whether it’s a threesome, whether they’re a couple, whether it’s one person. Every time you introduce sex into a relationship, you are risking that friendship. That’s part of the gamble of life.

Rich: Even if everybody’s on board and going into it equally, something could happen during sex that rubs somebody the wrong way. Then you might never do that ever again, or you won’t be friends anymore, or any kind of thing like that.

Jessica: Or it could go beautifully awry, where the couple decides that they want to be in a throuple and that’s more than the writer wants, and then that ruins the friendship because they feel disrespected. There are all sorts of ways that this can go sideways.

Rich: Definitely. I think that the writer needs to understand that they do have some power here. They are basically offering themselves up as a unicorn, and that’s a highly prized status by couples who are interested in non-monogamy. So, tread lightly, sure, but know your own power here as well.

Jessica: Between the breathlessness of the letter, the capitalization of Lady, and the writer seeing their role as subordinate, I’m also wondering if there’s a power dynamic here.

Rich: Right.

Jessica: And also, if it’s a Victorian-era-esque kind of take on BDSM. That’s maybe something to consider because fantasy can get in the way of seeing reality. It can lead to misreading the situation and blowing up the friendship, or missing the opportunity to have threesomes with this couple.

Rich: Say the flirting suggestion doesn’t push things along in a satisfying way for the writer. What do you think would be the best way to broach this conversation? I think that the writer could verbally recall the time that they all went home together, and ask what was up with that. Maybe they start the conversation there.

Jessica: If our writer’s up to it, which I’m not entirely sure they are—this might not be their style—but I would say directly to this woman, “Hey, I would love to have a threesome with you and your partner. I think you are so attractive. If there’s interest on your end, I want you to know I am totally in.” It may not be as romantic, but it’s clear.

Rich: Yes. That kind of clarity is probably going to be the most useful here because they’ve been kind of dancing around this. The guy’s already on board, and I think it’s actually very mature of our writer not to assume that the woman is as well, just because the guy is. That’s really smart. But at the same time, you have a little bit of assurance there because you’re not watching them fight about this in front of you. They brought you home.

So, I think—again with the unicorn thing—there’s a little bit more confidence baked into this situation that you could hone in on if you’re so inclined. You can move forward knowing that these people are probably into you. Everybody’s probably thinking the same thing. So, to say, “I want to have a threesome with you,” isn’t as much of a plunge as if there’s been no indication and this just popped into your head, and now you’re trying to make it happen.

Jessica: Or, if you’re the man in the triangle and you haven’t discussed this with your female partner, or the third woman.

Rich: Totally.

Jessica: I do want to add that if there is a tendency toward power exchange for the writer, and that’s part of what gets them off, be clear about that as well. Be clear in one conversation, or a few if it takes longer than that, to negotiate everything. Then with that groundwork laid, they can enact all of the grand fantasies that they might want to. They’re still going to have to be clear at some point, and sooner is better than later. Like, “Hello, I want to capitalize the words I use to refer to you. I want to write you love letters. I want to worship at your feet.”

Rich: Yeah.

Jessica: Whatever it is, because that’s how you allow everyone to have an enjoyable experience.

Rich: I’d say use the love letter option as your last one, if you really can’t get the words out. If you can’t have this conversation, then OK, write her a love letter. But I think that some people, me included, don’t like the indirect approach. That’s points off for me. That could be a turnoff unless I’m really attracted to the person. There’s nothing worse to me than somebody in a bar saying, “Oh, my friend thinks you’re hot.” That’s already like you’ve shown me way too much about your lack of assertiveness, and we’re off on a bad foot. It doesn’t mean it’s a definite no. It’s just always kind of like, “Ugh, really? We’re doing this?” Somebody might feel similarly about the kind of indirect approach of a letter. It might kind of be a turnoff to not actually speak about it, but if you have to, so be it.

Jessica: I have a hypothetical scenario in my head that I just have to get out.

Rich: Please.

Jessica: If they’re a part of a historical reenactment society, then lead with the love letter. Otherwise, it’s not a thing that most people are going to be familiar with and have any idea how to navigate. So, we might end up with another letter to How to Do It along the lines of, “I have received a suggestive love letter and do not know how to proceed. It is from another woman. Is she suggesting friendship, or is she trying to get in my pants? Because I would love to have a threesome with her.” Just because that sort of thing is out of the norm of how people approach each other now.

Rich: Definitely.

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