How do I tell my best friend I'm sleeping with his sister?

Two years ago I started sleeping with my best friends younger sister (I'm 32 she is 23). We've kept it quiet because at first we thought it was just a sex thing, then friends with benefits, but now it's turned into a relationship. She wants to move in with me and I would very much like that too. But we have to tell her brother my best friend since I was five. We've already told his wife and she was fine with it. She thinks we are great together but she agrees he won't be. Any ideas on what we should do to make this easier?
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Most Helpful Girls

  • Tell him you're in a relationship with her. Don't mention that you were just having casual sex at first because this will make him made but i'm assuming because you're in a relationship with her, you care about her? Tell him that.
    If he doesn't approve, well, if you like her enough, that won't matter.

  • "So uh funny story, remember the time I told you I was sleeping with your sister? O I didn't.. well anyway she's my girlfriend now.."

    • O and be ready to duck..

    • You think that's funny but seriously it may be like that...

    • I was being sarcastic/joking... goodness. anyways just tell him truth.. both of you tell him. Hey we're dating and I just wanted you to know before you found out. If he gets mad.. let him calm down for a while then talk it out with him.

Most Helpful Guys

  • The sister is 23, a grown woman. It's time for her brother to understand that she's gonna live her life her way and if he wants to be part of it, he has to back off. You should tell him together but let her do the talking.

    Why particularly will he object?

    • Well in all honesty he's very protective of her, and to be blunt he still thinks she's a virgin. He doesn't know I've been having sex with her since before she was old enough to drink. And he knows me and what I've done so he will want a "better" man for her

    • It's not his decision. It's hers and hers alone. She should tell him to 1) keep his opinions to himself, and 2) be happy for both of you. She can control him. Let her handle him.

    • That's wise, but he's like a father to her. She idolizes him, and he's had my back since first grade. Part of me hates I've done this to him but I do love her. So this is going down one way or another, just wise it was like easy

    • Show All
  • Nothing you can do to make it easier. You kept it a secret WAY too long. He will be pissed either way. I know I would be. He'll get over it eventually but it's a lot to handle at one time.

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What Girls & Guys Said

3 1
  • That's a tough one... it might end your friendship and might turn into a fist fight.

  • What he doesn't find out won't hurt him

  • Even if he's not okay with it does it matyer

    • Matter*. It's yours and her decision. I'm sure he'll come around eventually

  • He won't like it, better to keep it quiet for a while and wait for the right opportunity