Man Discovers He Slept With Girlfriend's Boss & Has No Idea How to Tell Her

Man Discovers He Slept With Girlfriend's Boss & Has No Idea How to Tell Her

Working from home has enlightened us to plenty of our partner's quirks. We're learning that some of our loved ones have a "meeting voice," that they say things like "circle back," oh and that we might have slept with there boss at some point.

Well, that's at least the unfortunate case for one man on Reddit.

Man Discovers He Slept With Girlfriend's Boss & Has No Idea How to Tell Her

Before meeting his now girlfriend, the Redditor says he was in a casual "friends with benefits" situation with someone for around five months. He and his current girlfriend got together just a month after he ended his casual relationship, and he never thought that the two women would ever intersect in life.

But being home 24/7, he made an unfortunately discovery while walking pst her Zoom meeting.

Man Discovers He Slept With Girlfriend's Boss & Has No Idea How to Tell Her


Sure as the sky is blue, when he glanced at the screen, he discovered his girlfriend's boss was in fact his former friend with benefits.

"I don't know how I could bring it up without making it seem like a big deal," he confessed. "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."

Some people assured him it was better to just bite the bullet and tell her.

"It’s great that you want to be honest with her," commended one Redditor. "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."

But others thought it might be unnecessary information.

"You explain honestly that you didn't want to ruin her experience at her job because let's face it, she will never look at her boss in the same way again and if she is particularly jealous she will quit the job. Nothing good can come out of it telling her, and it's not like OP did anything wrong," warned one reader.

And another warned that it could have some effect on her wanting to stay at the job.

"I don’t know why people are saying not to tell her," admitted one reader. "Of course it would be better for her not to find out at all, but what if she finds out from someone else? That would be so much worse."

They then followed up with...

"That said, if I was your girlfriend, I would want to leave my job over this. It’s too weird because she’s in a position of authority over her, not just another random coworker."

Which is exactly hat the confuse boyfriend feared.

"That's what I was thinking," we responded. :She really likes her job and I wouldn't want to interfere, but her having authority makes it weirder."

Though all in all, most agreed that finding out form him was the best way it could happen.

"I think the best way to go about this is gently," they retorted back. "Maybe have some snacks on hand she really likes or do something nice for her like a foot rub right beforehand. Then break it to her as gently as possible. In my experience, even when something is super uncomfortable and I’d rather not know it on a superficial level, I’m always happy that someone trusted me enough to be honest with me even though the truth may hurt and isn’t pretty."