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

January 4, 2014  |  


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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  • Amy

    My best friend is currently dating my brother (And only after a month of meeting him..), I’m not thrilled as they went behind my back for it, and he did this one other time with another one of my friends…
    This ones getting rickety with both my friend and my brother… I’ve been trying to be okay or at least act okay with it but not working so well.
    My brother and I aren’t on talking terms,. and she isn’t the happiest with me… Then again I did lose my cool when they decided it was okay to make out in front of my little brother in a shared bedroom while he was sleeping bedroom, in front of a five year old girl and then in our dorm room last night when I was trying to sleep and it sounded like they were doing more then making out not full on sex but still…
    So yeah I don’t think its a good idea.

  • kim

    A (now ex-) friend started dating my brother and lied to everyone about it. It led to fighting and ultimately ruined our friendship.

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  • sugabay87

    My best friend tried to push up on my sister and I shut that down quick. If u looked up blocking in the dictionary my face would be right next to it. He was tryin hard to get to my sister too…

    • jess22

      Ur sister is gonna spread her cheeks for someone. So who cares?

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  • swtchocolatykizz

    I just feel that certain people should be consider “off-limits,” unattainable to you. This includes a best friend’s brother, father, uncle, cousin(did I leave anyone out). When the relationship doesn’t work-out now you have to deal with the awkwardness of seeing them @ a function. Or what if you do something real foul so much so that now your best-friend is pulling your coattail about it…now you conflict and a lost friendship! A lot people think when they come of age that it’s open market on and it’s fair game because they are consenting adults…..well I say nothing doing, there should be boundaries where your friends are concerned(if you really are a true friends).

    • acb87

      what i it works out ? your going to stop a friend and a relative from finding love and possibly building a new family together ?

      • Martha

        I’m in this exact predicament; my best friend and my brother are dating, and although I’m not preventing them from having a relationship I don’t believe that I can necessarily ever love them again and losing a sister and a friend is nearly as major as a breakup…

    • jess22

      Ur stupid and a control freak

  • mglass22

    I married my besties brother….is that allowed lol

  • cols oh

    It is a terrible idea. I did it and at the time I didnt see the big deal, yet we still weren’t upfront with telling everyone. I told my best friend right away but her family, who had watched me grow up, were gradually told/shown that we were a couple. Eventually we had a baby and everything went down hill when he became a deadbeat. One of the sisters even tried to act like she wasnt certain the baby was his! Paternity test and years later, things still arent the same. Just dont do it.

    • getovait14

      Lol! Maybe it was you!

  • justsayin

    Although I understand the writer’s closing points, I feel that two grown consenting adults should be able to do as they please. The pickings can be slim enough and I think it is good to get with someone that you know and feel comfortable with…a person whose character you can vouch for before getting into a relationship with him. It makes the process of dating much easier and establishes a level of comfort from the beginning. This is something that usually takes time to develop in other traditional dating/relationship scenarios. I see no problem dating your best friend’s brother, cousin or uncle!

    • Martha

      Maybe it helps the sexual relationship develop but trust me its not always the best thing for the friendship. My best friend has just started dating my brother and I cant stand to look at them, it makes me sick to my stomach with betrayal. I’m so worried I wont be able to get over this and I’ll lose them both forever, its a very tangible future from this point. So its always worth considering how your actions affect everyone in the situation. Although adults don’t need permission, doesn’t mean their actions don’t have consequences and in this instance it could be losing someone really important to you.

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  • Huh

    Am I tripping it did you kinda switch it up with friend’s brother and brother’s friend?

    • NVAdamzz

      They did. It made the article a little confusing to follow. They really should do peer revisions like we did in college. Someone would’ve caught that.

  • NVAdamzz

    Whether it’s love, lust or otherwise I think what 2 grown people decide to do with themselves is their business. My brother slept with 2 of my close friends but said I can’t talk to any of his friends unless it’s serious. He says he knows it’s a double standard but it’s one that he is sticking with. I didn’t care that he and my friends messed around but he didn’t ask if I cared.

  • Meliss

    this article is CONFUSING. the title says best friend’s brother, then switches back to brother’s best friend. Good God.

  • Laine

    hmm… it’s supposed to be brother’s best friend…and not best friend’s brother….jeesh

  • Nya Jacobsen

    I dated my best friend’s brother. She didn’t want to hear about my sex life anymore and no venting like I could do with previous boyfriends. And note to the author I’m black.

  • Angela R. Ingram

    I forbidden my friends to date any of my brothers. Not a good idea. Yes I said forbid. I don’t date their brothers either.

    • Stacy

      You’re right my friend dated my best friends brother needless to say it didn’t end well, although my best friend still remains friends to this day, things r very awkward also she can’t come to events when my best friends brother is coming.