Dating Your Best Friend’s Brother: Is That Acceptable Or Too Close For Comfort?

January 4, 2014  |  

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Finding a great guy to date nowadays seems impossible for some women, so when she finds what seems like the perfect guy, she should go for it, right? He’s cute, he’s funny, smart and you two really seem to hit it off. You like him and he likes you, so what’s stopping you two from hooking up? The dilemma: He’s your best friend’s brother. What to do?!

A girlfriend of mine found herself in this predicament. I didn’t quite see anything wrong with it…at first. I mean, what’s the big deal about dating your best friend’s brother? She had known him for years and he was a great friend of the family. They flirted here and there, but her brother just chalked it up to his younger sister having a little girl crush on one of his friends – until she came of age. At first, she started seeing her brother’s friend behind his back, but once it got serious, she confessed that they had secretly been dating. Needless to say her brother wasn’t too thrilled about it.

When I asked her why her brother was upset, she said her brother’s explanation was simply, “That’s just not what black people do.” I could see if he was upset because she kept a secret from him or because maybe he thought his friend wasn’t good enough for his baby sister, but to make it a cultural thing seemed strange to me. Then again, I had known many white people who had no problem dating their best friend’s brother, but no black folks. Maybe I was just oblivious.

I don’t have any brothers, so I can’t say how I’d feel if my bestie wanted to date my sibling. I’ve also never been attracted to any of my girlfriends’ brothers, so I’ve avoided that conflict altogether. But I would imagine that if I thought very highly of both my brother and my best friend, why would I have an issue with them dating? Logic would suggest that you’d want two of your favorite people to be together right? Not so sure.

One thing my girls and I did growing up was talk about the boys we liked, dated, kissed, hated, and then kicked to the curb. But imagining my girlfriend talking to me about kissing, getting intimate or even hating my brother would probably leave me feeling a little uneasy. Who wants to picture their sibling getting busy with anyone, let alone with your best friend? I can see how it would get tricky and, possibly, messy. What if they break up? Are you caught in the middle? Just the thought of all the “what ifs” is too much for me and I’m not even in the situation.

Once I weighed the pros and cons of dating a friend’s brother, I began to see how it might not be worth all the potential drama. I’m not saying it could never work out, but I’d have to make sure that the guy I’m interested in would definitely be worth the risk of losing a friend. Either way, if this is something you’re thinking of doing, be sure to cover all your bases.

Make sure the guy in question actually likes you as much as you like him. If not, there’s no need to open a can of worms. If you both decide this is something you want to pursue, don’t sneak behind anyone’s back. Make sure you talk to your bestie first to see how they feel about the possibility of you two dating. Not that you need permission, but definitely consider their feelings and their point of view. If your friend thinks it’s a bad idea, ask why and really listen to the answer. Chances are they know him way better than you do and could possible spare you some heartache. If you decide to date the guy anyway, keep your friend out of your relationship. If you break up down the line, keep the details of the breakup to yourself. Handle it in a mature, discreet way so that all parties can remain friendly afterwards. I know it’s not fun to think of the end of the relationship before it actually begins, but this is something to keep in mind.

Last, if you’re not absolutely sure you’re in love and you think it could just be puppy love (or lust), find someone else to date. I know the pickin’s may seem slim, but some friendships are just not worth losing.

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