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The original was posted on /r/AmItheAsshole by /u/StephenIsAwesome5432 on 2023-09-09 18:35:27.

I (M, 32), and my fiancee (F, 27) met 3 years ago and immediately hit it off. We very rarely argue and have had a very healthy and vibrant relationship. I proposed to her about 6 months ago and she said yes, she has slowly been putting together arrangements since then. This is where her best friend (M, 27) comes in. They were best friends in middle and high school and have remained very tight since then. We’ll call him Leonard, Leonard has been a gay man for as long as I’ve known him and also has a long term partner too, let’s call him George. This is where things get a bit weird.

My fiancee told me a few days ago that she had something to tell me, turns out that during highschool she and Leonard experimented together and that he actually took her virginity. It was this event that supposedly allowed him to realise he didn’t like women and accept his homosexuality soon after. I knew that she had, had several partners before me - that isn’t an issue, the issue is that she has such a close friendship to this day with one of them and that she didn’t disclose this to me sooner. She told me she wanted to be clean with me about this before our wedding and that she intends to have him serve as her “groomsman of honor.” I told her absolutely no way in hell. I will not have someone she has been intimate with at our wedding and the fact she didn’t disclose this long ago feels like an enormous betrayal.

Leonard’s partner George was also unaware for the record. It has now become a battlefield and both George and I are demanding that Leonard and my fiancee create boundaries and distance. George also agrees that I am being very reasonable in not allowing Leonard to attend my wedding. My mother thinks I’m overreacting and says that people experiment in highschool, that they’ve had a platonic friendship for many more years than a romantic one, and so I should get over it basically. My dad is as usual sitting on the fence to avoid ruffling feathers. She doesn’t have parents I can consult about this, but her elder sister agrees with me 100%.

I have given my wife an ultimatum: distance yourself and create boundaries with Leonard, or lose me. These two have had sleepovers, held hands as “friends”, and gone on dinners alone together whilst we’ve been dating. Had I known about the fact that they had, had this relationship there is no shot I would have allowed any of this. AITA?