"My boyfriend almost had a threesome while we were on a break"

So can she still spend the rest of her life with him?

Original column: Ask Anna, May 30 2024

My take: The LW and her boyfriend recently took a break. She just learned that during the break, he “had conversations with a gay man who offered him a threesome with him and some hot chick.”

She already knew her boyfriend is “into pre-op trans women.”

Her boyfriend tells her he hasn’t acted on any of these interests. Still, the LW is “overwhelmed with anxiety.” She writes: “I love him and want to spend the rest of my life with him,” but now she thinks he might be gay.

Anna’s response is just awful.

She’s insufferably patronizing (“it’s OK to feel confused and anxious” about “thoughts that might be outside of your comfort zone or what you expected”).

Ick, right?

Anna asks the LW, “why does the almost-threesome idea hurt you so much?” Why does it “translate to a fear of him cheating on you and leaving you for a man?”

You, readers, may think it’s because the guy told her he’s into the pre-op trans male body, and had multiple conversations about having sex with a man (plus a woman). But to Anna, this means nothing. “Plenty of straight men have (or want to have) MMF threesomes,” she writes airily.

Anna’s source for this claim is a guy who has a “Ph.D. in threesomes.” Even if we assumed that Ph.D. is legit (which is a reach), and accepted that meaningless word, “plenty” (which I don’t), what does “want” mean? Is it idle curiosity? Or do “plenty of straight men” want threesomes badly enough to entertain actual conversations about it, and report those conversations to their girlfriends?

In the end, Anna counsels a talk with the boyfriend. The LW should “express how his almost-threesome offer has made [her] feel, [and] the insecurities it brought up.” I’ve said this before, but I’ll say it again: Accusing a woman of insecurity, when she knows or reasonably expects she’s about to get cheated on, is just insulting. And this LW’s expectation is most definitely reasonable. Her boyfriend told her he’s thinking about cheating!

Also, Anna says the LW should tell her boyfriend some of her own “fantasies.” To expand her “very limited” sexual proclivities! Did I mention that Anna was patronizing?

Advice Obsessed (sorry, no Ph.D) will now dig into that business about the threesomes.

First, common sense says a threesome is dehumanizing. It reduces sex to impersonal sensation. It strips sex of intimacy.

Second, history is instructive here, because a lot of this stuff has already been tried. And letters like this one tell me some people don’t know that. They don’t remember the original free-love generation.

To condense a lot, in the 1960s people loved to say “sex is beautiful.” Early sixties songs are all about how we don’t need to be married to do this beautiful and natural thing; if we love each other, that’s enough.

But, once detached from marriage, the love business soon dropped out, and “sex is beautiful” became “if it feels good, do it.”

What can I say? There were many casualties. Sex isn’t always beautiful, it turns out. Sometimes it’s downright ugly. It’s responsible for some of our best experiences, but it’s also responsible for some of our worst.

Today people like Anna, and the LW’s boyfriend, are reverting to “if it feels good, do it,” and history says they’re playing with fire.

Anna chides: “Remember, many people fantasize, wonder about or want to actively explore different aspects of their sexuality, and this doesn’t diminish their love or commitment to their partner.” She’s wrong. It absolutely can, and it does.

Anna treats the LW like a child. I am so sick of people belittling women who want their sexual partners to love them, and who want that love to last.

I’m guessing the LW and her boyfriend are youngish. Some young people do experiment. If that’s what the boyfriend wants to do, nobody’s going to stop him. We may be concerned about him, but we don’t interfere.

But we know that what he wants is totally incompatible with the enduring love for which the LW longs. Anna should have known this. Anyone should have known this. A better advice columnist would have told the LW the truth, and advised her to move on.

Posting this one under Best Question, Worst Answer.