Our best man once slept with my fiancé. Should I kick him out of the wedding party?

Hi Jake,

My fiancée and I are getting married in a few months and I’m really excited. Planning the wedding has been a lot of fun. We decided for our wedding party we’re each going to pick four people, eight total, to stand beside us. I have an issue with one of his four picks, however. It’s his best friend from college (I’ll call him “Matt”) who I am 95% sure he used to hook up with, although we’ve never actually talked about it. He and I have a rule that we don’t discuss old hookups/flings/relationships since it’s in the past and we’re focused on the future. I like Matt and I don’t mind if he’s at the wedding, but having him in our actual wedding party and the photos doesn’t sit right with me. I’m afraid I’ll always look at them and think about how he used to have sex with my husband before we were married. So, what do I do?

Fuming Groom

Dear Fuming Groom,

This is an incredibly happy time in your life, but I worry you may be letting something fairly innocuous taint something otherwise joyous and celebratory. You and your fiancée found each other, despite all odds, and have chosen to commit to each other for the rest of your lives. There’s clearly a strong and sacred connection there, and that goes beyond relationships and sexual encounters from long ago.

I’m hearing you might be threatened by the idea of your partner having a past, and even thinking about him sharing intimacy with someone else triggers certain feelings in you. There could be something here for you unpack, perhaps in therapy with an LGBTQ therapist who gets you, so that you can understand what those jealous or insecure feelings are about. They may actually have more to do with you, rather than your partner, because it’s perfectly normal for him to have a past. Former flings say nothing about where things are today, including the intensity of your bond or your physical connection.

The important thing to remember here is that your fiancée is walking down the aisle with you, not Matt. You won the prize, and that should supersede any previous history. It’s rather common for gay men to initially connect sexually, but after some time, realize the sexual chemistry is gone, and what’s there is a deep sustaining friendship. We can seamlessly go from “friends with benefits” to just “friends” without carrying any baggage forward, and that’s a strength. There was a time and a place for Matt, but this is now your era.

If it’s really difficult thinking about your future husband sleeping with someone else before you, or if you still feel threatened by him being in your inner circle, that might mean one of two things:

You may have some trust issues.

Are you worried that your fiancée might still want to sleep with Matt, and betray your commitment to you? If so, you should probably work through that before jumping into a life-long commitment. Healthy relationships are based on trust and respect. If you can’t trust your man to stick to his commitment to you just because he’s spending time with a former fling, is that really the best foundation to go into a marriage? Or, if there’s no reason not to trust him, but you still can’t, it may be connected to something in your own past. That’s worth processing in therapy so that you don’t bring it with you into your marriage.

You might be struggling with some insecurity or low self-worth.

When our self-esteem is low, it can feel like we don’t have a solid foundation, and anything may feel like a threat, even the very thought of your man being with someone else. If there’s no evidence that he would cheat on you, that means this is probably more about you not believing in your worth. You’ll want to get to a place where you value yourself enough to know that you’re a catch, and you can withstand the idea of your man having a past (or even finding another guy attractive, for that matter), because at the end of the day, you’re the one he lays down in bed with every night.

There’s always going to be temptations, but a marriage is a demonstration that you are putting someone you love in first place. If you’re not feeling deserving of that, some deep work may be warranted to sure up your self-worth.

As long as he isn’t crossing any boundaries, I’d say let Matt stay in the wedding party, and deal with your insecurities about it separetely. If it’s not him, there’s going to be some other guy that shows up in the future that triggers these feelings. Nip it in the bud now, and work on shoring yourself up. Your future marriage counselor will thank you!

Jake Myers, LMFT is the founder of LGBTQ Therapy Space, the first national platform for online therapy for and by the LGBTQ community. Answer a few questions here and we’ll match you with the best LGBTQ therapist for you in your state, for a free consultation! Jake is also accepting clients into his own private practice, and you can reach out for more info at [email protected]. Don’t forget to follow us on Instagram!

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