Tips On Dating A Friend’s Brother–Without Her Hating You!

dating a friend's brother

Dating a friend’s brother doesn’t have to be awkward, but you may all not want to be quite this close. | Source: ShutterStock

Dating your friend’s brother is tricky, and for some reason, I’ve done it a bunch of times. It’s not something I set out to do–I never had a checklist of pals whose siblings I was determined to conquer or anything–it’s just how my life’s particular cookie crumbled. But! I never had any drama before, during or after any of those relationships, because I was super careful how I handled myself, my guy and my friendships.

(And karma got me–one of my brothers married one of my friends. I wish she’d read this before driving me nuts.)

Dating a friend’s sibling requires a lot of sensitivity and careful thinking, especially if it’s your BFF, because jealousy and getting territorial are common. She may feel like she’s losing her bestie to her bro or her bro to you, and neither of those are good feelings at all. Here’s how to navigate the waters of smooching your BFF’s big brother!

Give her a heads up that it’s happening . . .
If your best friend is the last to know about your relationship, she’s going to feel betrayed or used. That is the last thing you want to happen, because you wanna get her blessing on this. Just let her know as soon a you guys start hanging out, “Hey, not to make anything weird, but Dan asked me to a movie by ourselves Friday. Is that cool with you?” The more honest and upfront you are with her, the less likely there will be any problems.

. . . But don’t gush about your relationship.
To your bestie, her brother is still someone who farts too much and spends way too much time quoting Adam Sandler movies and playing Call of Duty–and that’s why she loves him. Let her keep that image alive. And on that note . . .

No PDA in her presence!
You don’t want to see your little sister playing tonsil hockey with anyone, right? Or your parents getting gropey? Then for the love of all that is good and holy, don’t put your best friend through this.

Hang out with her solo.
While it may seem convenient to date someone who lives in the same house as your best friend, it doesn’t mean you should walk around like a mildly incestuous version of Three’s Company. Keep your outings separate and don’t forgo seeing your BFF to hang out with your new BF, otherwise she’s going to resent you–and you’re going to miss her.

Don’t vent to her after a fight or badmouth her brother in any way.
This is so important. Even if he’s completely wrong and acting like a douche–say, ignoring your calls in favor of hooking up with an underage girl who lives nearby (not that that’s happened to me or anything, ahem)–DO. NOT. TELL HER. It’s still her brother, and all you’re going to do is create drama. If you need to, keep a diary or spill to someone else who doesn’t know anyone involved personally. You may be her BFF, but that’s her blood. It’s not your place to ever try getting between that.

Have you ever dated a friend’s brother? Have you ever had a friend date your brother? How did you deal? Was it awkward? Tell us in the comments!

What happens if your BFF wants you to dump her brother?

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2 Comments

  1. avatarChoco13 says:

    So it can work? (Please say yes. Please say yes. Please say yes.)

  2. avatarElle_est_Maddy says:

    Oh My God if any of my friends ever did any of these or just dated my brother at all, I would not put up with that crap. Actually, if anyone in my grade I knew did that, I would personally induce a coma on that unlucky girl. Yeahhh…. I guess I might be a little overprotective(is that how its spelled?) of my older brother… :)

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