Ask A Guy: When Is It Okay To Date Your Brother’s Friend?

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Hey Joel,

One of my older brother’s friends has expressed interest in wanting to date me. My brother and he are practically brothers and I’ve known this guy for a while and think we could work together. I’ve never been in a relationship and have no idea how my brother would react to this. I don’t want my brother to lose a friend but I also want to try things out with this guy. I was thinking that maybe I just shouldn’t tell my brother but that doesn’t feel right. Help, please, I’m super confused on what to do.

First off, the absolute worst thing you can do is try to hide this from your brother. There is no way whatsoever that keeping things a secret can end well for you. If things go poorly, he will be mad at his friend for hurting you and doing things behind his back. If things go really well, when you eventually tell him, he will still be mad that all of this was going on behind closed doors.

Before the two of you even consider planning a night out, this guy needs to have a long talk with your brother. Dating your friend’s younger sister is about as much of a violation of Guy Code as you’re going to find anywhere, and it is his job as a friend and man to own up to the situation. Even if he has only the best of intentions, he needs to “clear things” with your brother before anything can happen. If he fails to do this, be prepared for a massive falling out between him and your brother, and don’t be surprised if you catch a fair share of blame as well.

However, even if your brother does give the go-ahead for you two to try things out, that isn’t necessarily the end of the problems for the three of you. As things progress, your brother might not be so thrilled to see his friend getting personal with you. That is to say, most guys aren’t really okay with their friends making out with their sisters. It is a complete redefinition of relationships for everyone involved, and it usually causes far more headaches than it’s worth.

That all being said, the core question of whether or not things could work out with your brother’s friend is no different than any other guy: maybe. You already know him and that he isn’t outwardly a jerk, so that’s a good thing. If you think your brother is an okay guy, then his friend is likely similar, and that’s also in his favor.

But in the end, with all the ins and outs, my advice is to stay friends with this guy, let him stay friends with your brother, and go look for love elsewhere. It’ll be less stressful, and likely more successful.

Best wishes,

Joel

Joel Freimark has done a lot in life and seen even more. From last minute international travel to bizarre places to writing award winning books, he’s here to bring his wisdom to all your problems. He hosts a weekly advice series on Youtube and a music series also on YouTube. No question is too outrageous or personal, so go ahead and fire away! Follow him on Twitter.

Are you confused about a guy? Do you find yourself wondering, “What is he thinking?” Tell us everything in the comments! And if you have a question for Joel, email him at askaguy@gurl.com!

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  • Kloo14

    I used to talk to my brothers friend last summer and we went out with friends as couples and would talk on and off but lately he had expressed interest in me and has taken me out on really cute dates late at night and he helps me sneak out so we can go out. I don’t know what are we and we don’t talk about what we are although we do couple things and we don’t text much because he’s in college and I’m in high school but we both understand that were busy and makeup for lost time when we’re together. My question is what do you think he thinks of me and us and I know sneaking behind my brothers back is bad but what does that say about this guy ?

  • Kloo14

    I used to talk to my brothers friend last summer and we went out with friends as couples and would talk on and off but lately he had expressed interest in me and has taken me out on really cute dates late at night and he helps me sneak out so we can go out. I don’t know what are we and we don’t talk about what we are although we do couple things and we don’t text much because he’s in college and I’m in high school but we both understand that were busy and makeup for lost time when we’re together. My question is what do you think he thinks of me and us and I know sneaking behind my brothers back is bad but what does that say about this guy ?