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Guy Doesn't Know What To Do After His Girlfriend's Boss Turns Out To Be A Woman He Used To Sleep With

Trust should serve as a foundation for any relationship, but does one's sexual history have to be fully disclosed?

That is what Redditor "ThrowRA-helpneeded2" is struggling with after seeing a familiar face on his girlfriend's laptop during her Zoom meeting.


Prior to meeting his girlfriend, the Original Poster (OP) was involved in a "friends with benefits"-type relationship with her boss.

He remains conflicted on whether or not he should come clean, so he asked the Reddit Relationship Advice community for help.

"Initial disclosure: I didn't cheat on my girlfriend. This happened before I met her. Bare with me if things get confusing."
"I slept with her boss before meeting her. She had barely finalized her divorce at the time and wasn't looking for anything serious."
"It ended up a fwb situation for about five months."

As fate would have it, two worlds collided.

"At that time my gf's boss worked for a different company before moving to the company my gf works for. I met my gf a month after breaking off the fwb (almost 4.5 years ago).
"A few days ago my gf had a Zoom meeting for work while I just casually minded my business in the background."
"I didn't know she in a meeting at first. Before I got up, to leave the room, I saw her boss on the screen."

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"She looked really familiar, but I didn't think it was her. Sure enough, it was. Later confirmed by her name."
"My gf really likes her job and by the looks of it, she also likes her boss."
"I don't know how I could bring it up without making it seem like a big deal. I did not know that she was my gfs's boss, but now that I do, I feel the need to tell her just for the sake of honesty."
"Any advice would be appreciated, thank you in advance."

Some suggested that being matter of fact in communicating is best and respectful in a relationship.

"Just tell her."
"So, I need to tell you something. Before we were together, I was in a FWB situation with a woman that ended a couple months before we met."
"I just learned from your Zoom meeting that she works with you. I just want you to know because I want to always be honest and up front with you because I care about you and respect you."
"Or something to that nature..." – zeporscheguy

The OP was complimented for his transparency.

"Right. Like, 'It wasn't a big deal, and it was a long time ago. I know if I hid it that would make it seem like I was hiding it, plus I value honesty in our relationship.'" – ValkyrieSword
"It's great that you want to be honest with her!"
"I think just sitting down with her and telling her would be the best thing to do. Since it was 4 years prior, which is quite a long time, I don't think that it should be too big of a deal."
"If my boyfriend told me this, I might be a little uncomfortable at first but the time frame would definitely not make me as anxious. Just make sure that you establish the terms of the relationship (fwb) and the timeline."
"Hope this helps and best of luck!" – Ok-Peak

This Redditor advised not to let too much time go by.

"I agree with this approach. I see most of the other comments say 'don't tell' or 'delay,' but IMO you want to get out in front of this."
"What if the boss sees your photo and it comes out that way, at work or a work happy hour? Then gf will come back to you and you'll either be truthful (I knew and didn't tell you), setting gf up for embarrassment or distrust, or you'll lie and say you didn't know."
"I don't see any good outcome in not telling, bc truth will come out eventually."
"If its not a big deal, better to do it now...and if it is a big deal, better to deal with it now then when you're both further invested."
"Hey...I saw your boss on Zoom the other day. Crazy story, I had no idea it was the same person, her and I dated casually for 5 months over 4 years ago."
"It drifted off or we mutually ended it and I haven't seen her in xx years, until I looked over your shoulder. Crazy right?! I wanted you to know in case it ever came up." – CRE_Energy
"Right now OP has control over the situation. Sooner or later it's gonna come out. So why not have it come from his mouth?"
"If OP waits and her boss tells her, there will be 100% worse. And much worse if it comes out years from now. This isn't a sitcom where things resolve themselves by the end. OP has no good outcome of this, unless he is honest." – mewashere1

Not everyone agreed that the OP should volunteer the information unless it was necessary.

"This is a tough one.."
"Up until the zoom meeting you were not aware what her boss looked like and her name. As far as your girlfriend is concerned you still don't know these two things correct?"
"I don't think you have an obligation to reveal your past history with her boss just because you accidentally found out who she is."
"Now if things changed and your wife developed a connection to her boss outside work (ie casual friendship, etc) or you were faced with having to meet the boss face to face with your girlfriend say at an office party (ie once return to normalcy happens).. Then I would say you have an obligation." – MadFerIt
"I think this would be the better approach, like others have said, by merely mentioning it, it could be percieved as a bigger deal than it is and start fractures on both relationships." – johnbreaks13337

The truth is, for most people, there was someone before you.

We all have a past, amirite?

"YUP! I'm a woman and if this were me, while it might be awkward knowing my boss had sex with my boyfriend, oh well! Consenting adults get laid, there weren't any feelings involved, it was before I knew him!"
"We all know our exes had sex before us and pretending otherwise is kind of silly."
"I think the best method may be to be very straightforward and also treat it like it's not a big deal (because it isn't)."
"Not that he should minimize whatever feelings his gf has about it (definitely don't do that, kiss of death!) but that if he makes it a big deal when he brings it up, she might think he has feelings about it he actually doesn't."
"So saying something like, 'Hey, this is a little awkward, but I saw your boss on the zoom meeting & before I met you we had a brief FWB relationship. No feelings involved & nothing big but I never want to hide things from you.'"
"Then he can just give her a minute to feel weird about it, cuz her initial reaction may not be how it's all gonna go down, it's just a weird thing to hear."
"If she's irrational, unkind, or cruel about it, that speaks to greater dysfunction in handling conflict and jealousy."
"Me, if my bf went out of his way to tell me an uncomfortable truth rather than hide it cuz it was more convenient, I'd know that's the type of dude I can really trust."
"Good luck OP." – PeteRepeats

In the end, he will score points for being truthful about the past.

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