Ask A Guy: Is It Ever Okay To Hook Up With Your Brother’s Best Friend?

Hey Joel,

I used to talk to my brother’s friend last summer. 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 it, but we do hook up. We don’t text much because he’s in college and I’m in high school, but we both understand that we’re busy and make up for lost time when we’re together. My question is, do you think he actually has feelings for me? And I know sneaking behind my brother’s back is bad, but what does that say about this guy?


Let’s get one thing straight before we go any further: your brother is going to be very pissed off when he finds out about this. There is nothing shadier than hooking up with your friend’s sister behind his back, and trust me, he’ll find out eventually. This guy needs to man up now if you want something more–but it sounds like you might be fine with how things are now.

Like it or not, every one of your questions comes back to one simple reality: you haven’t asked this guy for anything more than late night hookups, so why would he give you more? From everything you’ve said, he’s living the good life on every level, and the lack of communication and veil of secrecy completely works in his favor.

I am honestly not sure why his being in college has any impact on the amount you text. Everyone texts these days, and if he’s saying he’s too busy to text because he’s in college, trust me, that’s a total lie. There isn’t a person in the world too busy to drop a handful of texts each day if they really care. The fact that you let that be okay, and as you said, “don’t talk about” your actual relationship is all anyone needs to see what you are to him: a booty call. Nothing more. He helps you sneak out at night and doesn’t want your brother to find out. On top of that, you continue to let things go on as nothing more than late night hookups and the occasional text. If that’s not the definition of a booty call, then I don’t know what is!

If you want more from the relationship, you need to make your feelings and wants known to him. There’s a very good chance that he won’t have the same desires, but if you’re not into the current reality anymore, then it’s time for him to step up or for you to step out.

Best wishes,


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!

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