This is part of Breakup Week. We just can’t do this anymore.
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 about breakups with our readers. Have a question? Send it Jessica and Rich here. (It’s anonymous!)
Dear How to Do It,
I have a complicated situation, but I’ll try to be brief. My wife and I (both women) began having regular threesomes with a close friend (also female) about a year ago. It was fun, uncomplicated, and spiced our lives up during COVID, when there was really nothing else to do. But recently, we’ve realized things are actually quite complicated. My wife and I both fell in love with our friend, and she with us. We’re not in a place to explore a poly relationship—we’re already in the fringe being a same-sex couple in our small Midwestern town—but we can’t continue as a closeted triad because the feelings are real. We know we need to break up, and that at least one of us will get hurt. Our friend has said the marriage should be protected, but I’d rather be with her than my wife. I think she might agree, but I know she would tell my wife if I asked, so I’m afraid to until I’m certain of her answer. Unfortunately, I suspect my wife is thinking the same thing. We do all love each other and want to maintain a friendship if we can. How do we figure out how to minimize the hurt one of us will feel and decide who gets to keep our new love?
—Three’s a Crowd
Dear Three’s,
It sounds like you’re afraid of ending up alone, which is reasonable—it might happen, and losing our emotional connections can be soul-crushing. But it also sounds like you’re stringing your wife along as a backup plan if things don’t work out with your mutual friend and threesome partner. When you say “decide who gets to keep our new love,” I’m left wondering if you see her as an object to be won and had or even owned, and I can’t stop thinking about the story of King Solomon.
So, as the Biblical tale goes, two mothers—sex workers, which is probably why the story stuck in my head—walk into King Solomon’s court with one baby. Each insists that the baby is theirs, and that a (not present) baby who died belonged to the other. Solomon asks for a sword and says he’ll cut the baby in half, and that’ll be fair. One goes “OMG no, she can have it, just let it live” while the other says “half a dead baby is better than her getting the whole baby.” Solomon rules that the live infant should be given to the woman who was willing to give up her claim to preserve the baby’s life.
Your friend already told you that she thinks the marriage should be preserved. She wants the marriage to live. If you leave your wife for her, there’s a good chance she’s going to be reluctant to enter a two-partner relationship with you. If you say to her “I want to leave my wife for you, but only if you’ll have me,” there’s an even greater chance that she’ll be reluctant to pair off. And if you say “I want to leave my wife for you and have threesomes together,” she will probably wonder how you think the same thing won’t happen again with her in the role of less-valued wife this time.
Think long and hard about whether you’re actually invested in your marriage, and if you aren’t, the kindest thing is to leave. If you do leave, take some serious time to heal and get right with yourself before you jump into another relationship. No matter how this works out—including the three of you staying together—there’s going to be a risk of suffering for everyone. There’s no way to pitch this as less hurtful than it is. —Jessica Stoya
From: “My Wife and I Had No-Strings Threesomes With Our Close Friend. The Aftermath Wasn’t What I Expected.” (Nov. 23, 2021)
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Dear How to Do It,
Is it always a bad idea to hook up with an ex? I had a pretty serious boyfriend in my mid-20s—we even lived together for about a year and a half. Our breakup was messy—it was his doing, a total surprise, and it truly broke me at the time. Our friends ended up taking sides, and it blew up into a whole thing. We had a clean break—we never spoke again after he left our place and packed his things. I moved on and I can honestly say I feel completely healed from that era of my life. It feels like a lifetime ago. I’ve explored sex and relationships very widely since and I am currently single. Everything is great. Except for that he’s back.
Apparently, he just moved to my city and I saw him for the first time in years at a friend’s event. We chatted like normal, and briefly caught up. I know through friends that he isn’t seeing anyone right now—and also that he’s largely the same person, so I would never ever want to date him again. But seeing him again reminded me of the fun times and I’m so tempted to reach out and see if there’d be any interest in a hook up. Is that too messy? I know my friends would tell me not to—but my life is generally so buttoned up and “healthy” I wouldn’t mind a little mess.
—Too Much Mess, Though?
Dear Too Much Mess, Though?,
On principle, I don’t see a huge problem in boning an ex with whom you have become reacquainted. This is especially so if you are experienced with hook-ups and can easily draw a line between purely recreational sex and sex that may lead to a connection that is decidedly more intense. If you’re collecting bodies, it might as well be a body that you know fits well with yours. You know yourself—if you can truly double dip without making a meal of your ex, have at it.
In this particular case, I’m a bit more wary of giving you an unquestioning green light. You say that you’ve moved on, and yet you’re edging right back where you were before: in bed with this guy. Your self-awareness is showing signs of limitations and that could mean bigger problems down the line. What if this thing that you’re sure you can handle, no big deal, turns out to be a big deal? That point is adjacent to the other issue here: actively seeking drama. Please do not intentionally step into mess. It is one thing to reconnect with someone because you know good sex is guaranteed. It is a different thing to hurtle yourself into some drama. This is probably why your friends would tell you not to—also, during whatever fallout should materialize, they’ll likely be the ones that are tasked with support/picking up the pieces. Your bad decision for the sake of fun may be a drain on their resources. If there is no shortage of available dick in your area, I’d encourage you here to continue exploring that which is uncharted and forget the ex. If you want drama, get into martial arts, reality TV, or your immediate area’s subreddit. —Rich Juzwiak
From: “I Just Ran Into My Ex. My Friends Are Begging Me Not to Do the Thing I Want Most.” (Nov. 8, 2025)
Dear How to Do It,
I’m a 27-year-old straight woman. I recently dated a man for several months who was odd about sex—he frequently mentioned that he had a small penis (which he did) and that oral sex was what made him a good lover. I don’t particularly care for oral sex, but I cared for him very much. There were a lot of problems in the relationship outside of sex—he had a bit of a cruel streak, and then there would be an apology spiral—and we eventually broke up. I have moved on and am dating a lovely man, but yesterday my ex sent me an email saying that he was bottoming for men he met online the whole time we were dating. He said he’s straight but curious, and he felt he needed me to know, and wanted me to accept him. (I didn’t get any STIs from him, and he said he used protection.) I’m sort of floored: I’m not sure why he told me, and what this meant about our months together, which loom larger in my mind than they probably should. I think he should embrace his sexuality, but how am I supposed to respond to this information? He was an asshole and made me feel terrible as a girlfriend, but I’m thinking that he has a lot of repressed sexual shit and I want to be there for him to realize it. What do I say?
—Some Personal News
Dear Some Personal News,
If you want to respond, tell him you accept him as he is—questioning, mistake-making, and human. Then tell him how you feel. Tell him it hurt to be treated the way he treated you (including the sex you’ve just learned he was having without your knowledge—you didn’t get an STI, but that was still a risk he took on your behalf), and that you don’t quite understand why he’s bringing this to you now. Ask him for clarity. And, please, write back and let me know. I’m curious. Forgive him, if you feel forgiving, or omit it if you don’t.
See how he responds. If he’s working through his internal mess, contrite, and treating you decently, by all means continue to be there for him if that’s what you want. But don’t allow a return to the kind of behavior that caused you to break up just because he’s having a hard time or you see potential in him—and don’t hesitate to cut off contact if it goes there. —Jessica Stoya
From: “My Ex-Boyfriend Emailed Me a Jaw-Dropping Confession.” (Aug. 27, 2019)
Dear How to Do It,
I was in a relationship with a guy for six years. He was my best friend and was present at all my family events, all my personal achievements, and my great losses. Ultimately, we mutually agreed to part ways since he wanted to settle down and I wasn’t sure that’s what I wanted. We thought we could stay friends since we were so involved in each other’s lives, but our past kept complicating things. In particular, our inability to stop having sex. Eventually, he moved out of state. But every time he returns, and sometimes the only reason he returns, is so we can hook up. I’m not interested in hooking up with anyone else, he’s expressed the same, but we can’t maintain long distance without awful phone fights and disappointments. It’s like the only time we communicate well and effectively is during sex. Why can’t I quit this guy?
—Desperate and Dickmatized
Dear Desperate and Dickmatized,
You can’t quit this guy because you haven’t quit this guy. And you’ve put more than a little effort into maintaining your limbo: He moved out of the state but he’s remained a regular in your bed. The most practical thing to do would be to use the distance to your advantage and keep him away. Turn “sometimes” to “never.” Go cold turkey, undergo a cleanse. Treat him like a drug: A little of him is all you need to get roped back in, and it makes quitting that much more difficult. Break the cycle. Go enough time without, and get hungry for some contact/dick, and find someone else to which you can direct your attention. Breaking up is a process that takes time to get over (I don’t trust any studies/polls that purport to put a definitive number on just how long it takes). You just have to live out the withdrawal so you can renew.
Or, you could just lean into the fact that you (probably?) love this guy and you’re happier with him than without him. You broke up because you weren’t sure you wanted to settle down, but even at this point you do seem settled (you have no interest in sex with others at the moment). It’s just that you’re settled on shaky ground. It sounds like you’re still together but refusing to acknowledge it because you formally broke up. Those were just words. If you go this route and recommit, your first objective should be to alter the behavior that results in your fighting. You were with this guy for six years and he was your best friend—surely you know what it is to get along, and if you can’t get that back on your own, a couples counselor could potentially help your troubleshooting.
The one thing that’s clear is that it’s not tenable for you to stay in the half-relationship that you’re currently in. It’s either all or nothing—can’t be both! —Rich Juzwiak
From: “My Ex Has Me Trapped in a Sex Trance.” (June 7, 2023)