I Just Realized I Had A One-Night Stand With My Fiancée’s Sister. Should I Say Something?

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What would you do if you realized that your new partner’s relative is someone from your past? Would you say something to your partner? Would you pretend that you don’t remember and pray no one brings it up?

Recently, a man who we’ll call “James” turned to Reddit after meeting his new fiancée Janie’s sister for the first time. Apparently, the sister is someone he hooked up with ten years ago, after college and well, that made things kind of awkward during the holidays. James explains:

Ten years ago I was fresh out of college and starting my career. I was on a dating site and asked a girl a few years older than me out. She was really pretty, but it became obvious within the first hour of the date she wasn’t girlfriend material. Near the end, I made it clear I wasn’t looking for anything, but I thought she was cute. We went back to her apartment and had great kinky, dirty sex. I never talked to or saw her again. A couple of years later, I moved across the country for a job opportunity. Three years ago, I met the love of my life. She’s incredible. Smart, hilarious, ambitious with a great career, a total sweetheart, and an absolute fox. Here’s where the trouble is: we just got engaged over the holidays, and I couldn’t be more happy. I’ve never met her family so we recently went to go meet them since I will soon be a part of theirs. Well, we walk in the door and…yep you guessed it: my one-night stand from 10 years ago is her older sister.

Interestingly, James’ future sister-in-law doesn’t seem to remember the tryst.

I think I maintained composure on the outside but on the inside, I was freaking out. She gave absolutely no indication she knew who I was. No raised eyebrows, no flicker of recognition on the face, no double takes. Nothing. She smiled and greeted me warmly like the rest of her family, and that’s it. She also made casual small talk with me and chatted with my fiancée. She’s married now, and her husband seems like a cool guy. Now I can understand putting on a good show, but this one seemed almost too good. I am 85% certain at this point that the sister did not recognize me, and as far as she’s concerned, this is the first time she’s ever met me. My fiancée and I are back home, and I did a good job of getting through that visit without raising any alarms. Any nervousness I displayed Janie chalked up to just meeting her family for the first time.

Considering that Janie’s sister seems to be suffering from a convenient case of amnesia, James is wondering whether he should say something or just let it go.

I don’t know what to do. I don’t want to tell Janie I [expletive] her sister ten years ago. I don’t want to ask her sister, “Hey, do you remember me? Why? Oh, just curious!” I don’t want to lose Janie. If soul mates were a thing, she’d be mine. The only person who could possibly know what happened one night ten years ago is Janie’s sister, and I don’t think she remembers me at all. I’m so head [expletive]. Do I have to tell Janie? I really, really don’t want to lose her, and I certainly don’t want to cause her pain unnecessarily. If her sister had been a girlfriend and we’d been around the town together, that’d be one thing, but it was one night ten years ago!

What would you do?

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