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My roommate and her boyfriend of one year made a "monogamish" agreement over the summer: They are allowed to sleep with other people if it comes up, but they aren't supposed to "seek it out." Importantly, they've agreed not to tell one another if anything happens. She has never acted on it and I think she believes he hasn't either. I recently found out that he is sleeping with other women actively and that he has basically had a second girlfriend (who thinks he is in an "open relationship") for the past few months. They go on dates, kiss in public, etc. I think this violates the terms of the monogamish agreement and I am considering telling her. She has been very adamant about not wanting to know anything, but I don't think this is the level of infidelity she imagined when they made the agreement. What is appropriate here? Should I confront her or hold my tongue?

Feeling Relationship's Illicit Explorations Need Discussion

Your letter is a good example of why so few couples — straight ones, anyway — come out as monogamish, FRIEND. The anxiety around coming out as non-monogamous is its own thing, but there's also the pressure to constantly negotiate the opinions and concerns of others going forward. That's a tiring (and unsexy) process. (The fact that you're wondering whether you need to "confront her," your roommate, when she's not doing anything wrong but might be the wronged party here? That's a tell.)

Anyway, FRIEND, I guarantee you don't know as much about this monogamish agreement as you think you do. And there's a hell of a lot of hearsay in your letter. You say you "recently found out" that your roommate's boyfriend is "sleeping with other women actively." How did you find out? Who told you? Or have you seen it? Were you one of those women? Or has all that kissing and dating and fucking happened in front of you? Is this idle, malicious gossip directed at a couple that isn't conforming to the prevailing/default relationship model? Or do you have "receipts," as they kids said until they heard me saying it at which point they promptly stopped saying it?

And how do you know your roommate hasn't "acted on it" herself? Are you the roommate or are you the best friend/confidant? Are you the person she tells everything? Are you the person she would tell if she had fucked someone else or was actively fucking someone else? And even if she's told you she hasn't fucked anyone else, FRIEND, is it possible she senses your discomfort with open relationships generally and told you she hadn't fucked anyone else when she actually had fucked someone else? (Spoiler: It's possible.)

All that said — all that scolding done — if your roommate is your bestie and vice-versa and if she confides in you and if you're certainish the info you've got is good and if you're relatively certain she doesn't know what you know and would want to know what you know, FRIEND, then you should gently sound her out. (There are lot of "ifs" in that last sentence, which I've bolded to make them easier to spot.) Ask her how it's going, listen to her answers, ask a few obvious follow up questions, and then stir these questions in with a few innocuous ones: "If you don't want to know what he's doing, how would you know if he was doing something that violated the terms of your open relationship? Or is that something you'd rather not know? Would you want someone to say something to you if he were?"

Before blurting out why you asked that question, FRIEND, really listen to her response. It should tell you — she should tell you — whether holding your tongue is the right thing to do.

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