I Hooked Up With My Best Friend's Brother [Tuffy Luv]

Ask Tuffy Luv. By, you know, email. tuffyluvcc [at] gmail [dot] com and crap.
Dear Tuffy Luv,
So my best friend/roommate at school has a brother who is a year younger than us at the same college. Ever since we met we’ve hit it off, and always hang out at parties. With how much his sister and I get along, it’s obviously no surprise that he and I did, too. Whenever we would be flirting at a bar or party, she would make little comments like, “Omg, can you two stop.” The comments were neither mean nor serious, I could tell she just wanted us to know that she wasn’t digging our flirtation.
We managed to get through a whole year of harmless flirting, but on the last night of the year, our flirtation reached its peak, and we ended up hooking up… and things went pretty far (and by pretty far, I mean all the way). Afterward we were talking, and we both confessed our crushes to each other, but that we thought it would be best if we didn’t tell my friend/his sister about it. Her and her brother are super close, the year was over, and we just both felt that what she didn’t know couldn’t hurt her.
What I need advice on is how I handle this coming fall. Do I ever have any hope of having a thing with the brother.. or is having a thing with your best friend’s brother just too much of a weird, confusing, crappy zone to be in as a friend? Especially since we already have this huge secret from her? And do you think him saying not to tell her was so she wouldn’t be hurt by our actions, or did I just totally get used and should move on like nothing ever happened?
– Confused Friend & Crushing Hard
Dear Confused Friend & Crushing Hard,
Yeah, I think you two need to tell her. Oh, that’s not your question? Well– I think you two need to tell her. Seriously. It’s too weird. It’s too awkward. It’s going to ruin everyone’s good time.
So call your boy and tell him: We need to tell her. And then agree on it. He’s going to hem and haw and shoop, but don’t take no for an answer. Firmly but sweetly tell him you think it’s the best thing for everyone, and that you’ll be the one to do it.
And then tell her. But, like, not all the details. FOR FLOOP’S SAKE, NOT ALL THE DETAILS. Just, like, you know, your little bro and I have crushes on each other, and we may have had one little passionate night, and I couldn’t keep it from you because I love you way more. She’ll probably want details, but don’t give them to her. She’s going to be freaked out. There’s nothing you can do about it.
Just make it as minor and casual as you can, and maybe bring her ice cream or something when you do it. Yes. Ice Cream. Good idea, Tuffy. LISTEN TO ME. ICE CREAM. Like, in a cone. None of that pint crap.
Anyway, right, so once you tell her, then you can relax. If her reaction is, miraculously, that she’s totally cool with it (unlikely, but, hey, you never know), then you can pursue something with her brother. Otherwise, I’m guessing your friendship with your bff is more important than a little crush on her brother. So, um, like, choose the friend.
Hearts & Skulls,
Tuffy Luv

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