Dear Anna,

My fiancee and I have been together for three years, and I thought everything was great. Last night, however, during dinner, she brought up something that completely blindsided me: the idea of us each having a "pass" to sleep with someone else before the wedding. She said it would be healthy for our relationship and help us start our marriage with no lingering "what-ifs." She even claimed it would make our bond stronger.

I was shocked. In all this time, I’ve never thought about being with anyone else. Knowing she has makes me feel hurt and suspicious. When I didn’t react positively, she started backtracking, and now she’s been apologizing nonstop.

I’m at a loss. We’re supposed to get married in just a few weeks. I love her, but I can’t shake this feeling. Does she already have someone in mind? Was this just a moment of doubt, or does it reveal something deeper? Calling off the wedding feels impossible — we’ve been living together for almost two years, and everything is planned. But I don’t know how to move forward. Am I overreacting? — Considering Other Love Decisions Feels Extra Empty Too

Dear COLDFEET,

While I wouldn’t call it common, it’s not wildly unheard of for engaged people to want a last night of “freedom.”* (In fact, I’ve answered a similar question before, except the genders were reversed.)

The stereotypical bachelor or bachelorette party often skirts the edge of the “free pass” concept — a night of debauchery that can drift into a moral gray area. That’s why the other partner is often “not allowed” to attend. Think: Vegas trips, lap dances, questionable touching and drinking to the point of blackout.

I firmly believe that in a loving, respectful relationship, you should be able to talk about anything — even the hard stuff. Perhaps especially the hard stuff. It doesn’t mean you’ll always like or agree with what’s said, but creating space for open dialogue — without (too much) judgment — is a marker of emotional maturity and trust.

Fidelity is one of those topics that naturally stirs up big feelings, and for good reason.

Which is why couples should talk a lot more about their expectations of fidelity, particularly because humans are not historically great at lifelong monogamy.

Your fiancee’s timing and approach were clearly missteps, but it’s important to remember that she didn’t act on anything. She brought up an idea, perhaps clumsily, that she thought might serve your relationship. That’s not a betrayal; it’s a conversation starter.

That said, your feelings are valid. Being blindsided by the suggestion — weeks before you’re supposed to make a public, lifelong vow of faithfulness — would rattle a lot of people. It’s natural to feel confused, hurt, or even suspicious. But before letting those feelings take over, it’s worth trying to understand why she brought this up.

Your fiancee’s suggestion may have come from a place of curiosity or self-doubt rather than ill-intentions. She may genuinely believe this idea could benefit your marriage or help her enter it feeling “clear,” particularly if she doesn’t have much sexual experience. (Does she?) She might feel so unshakably confident and committed to you that a one-off night would not impact your relationship in the slightest.

However, her timing, delivery and suggestion have understandably created a rift. It’s worth acknowledging that she apologized, which shows she cares about how this has affected you.

But until you really talk to her, you won’t understand the whys and get to the root of things. Here are some steps to navigate this situation.

Choose a time when you’re both calm and can talk without distractions. Let her know how her suggestion made you feel — not in an accusatory way, but from a place of curiosity. For example: “When you mentioned a free pass, I felt hurt and unsure about where we stand. I’d like to understand more about what led you to bring it up, and why now?”

Encourage her to share openly, too. Does she feel unfulfilled in some way? Is this rooted in anxiety about marriage or fear of “missing out”? Understanding her perspective doesn’t mean you have to agree with it, but it will help you decide how to move forward.

This moment is a good opportunity to discuss your boundaries and expectations going forward. Ask yourself: What do I need from a partner to feel secure and valued? Then, share that with her. Likewise, ask her to articulate what she needs and hopes for in your relationship.

If this suggestion feels out of character and her actions otherwise align with being a supportive, loving partner, it may simply be a misstep you can work through. However, if this incident feels symptomatic of deeper issues, it’s OK to pause and reflect on whether moving forward is the best decision for you both.

Calling off or postponing a wedding is messy and painful — but far better than entering a marriage with unresolved hurt or doubt. (And, in the end, cheaper than divorce.) Trust your instincts, and take the time you need to decide what feels right.

———

*I find the idea of monogamous marriage as a kind of genital jail to be very weird, but here we are.

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