Ask A Guy: Here’s What To Do If You Want To Date Your BFF’s Older Brother

Hey Joel,

So my best friend has a brother, and she swears that we are perfect for each other. (He’s three years older than me) and their mom and dad both say the same. I just wanted to know if there was a way to tell if he actually does like me? He is WAY nicer to me than he is his sister, but is that just being nice? From what I know, the brother is always as mean to the sister’s best friend as he is to the sister?


While at first you might think that since this guy is your friend’s brother, there is some secret way of knowing more or different way you should approach the situation, it’s actually like any other guy you’re going to meet. Sure, you’ve interacted with him before, which at some level makes things less awkward, but insofar as his inner feelings are concerned, you need to play this like you’ve never met him. Take things slow, and let the sparks form naturally.

Much like when friends try to date, what you’re doing here is redefining the relationship you have with this guy. Up until now, he’s just been your friend’s brother, but the fact that you two might start dating puts him into a completely different category. With that in mind, treat the situation like any other first date, and be as cautious as usual in terms of letting things go too fast.

There is one other large concern that I have whenever you consider dating the sibling of a friend, and that’s how things can go bad if the two of you break up. Even if you and your friend are super close, if you date her brother and things fall apart, it can severely damage your friendship. Much like with her brother, the nature of your relationship with your friend will change if and when dating begins. Even if you try your hardest, you could lose both of them in the end, so think things through before you go one way or the other.

In the end, there are a number of benefits to dating a friend’s sibling, especially since you already know each other to a certain extent. However, a breakup can lead to you losing many important people in your life, so be sure you think it can succeed before you agree to anything beyond a casual first date.

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!


Ask A Guy: How To Tell If An Older Guy Likes You

Follow Gurl, Pretty Please!

FacebookTwitterTumblrPinterest, and Instagram

Posted in: Ask A Guy, Love Advice
Tags: , ,
  • emily

    I have a huge crush on my best friends older brother (3 years older) and she and all my friends say we act like a couple and hes protective and kind to me and always has a go at his sister when he thinks she is being a bad friend to me and she hates us being close but when I’m at their house she falls asleep really early and I usually end up in the lounge talking to him all night. I don’t know how to pursue him without losing her. My friends all think we like each other because he acts flirty with me. At her new years party, there was 4 girls including said best friend, and her cousin and brother (both 18). Lets just say we all got very drunk and all night we were kind of acting like a couple? It was very touchy feely( he had his arm around me and just favourited me) and him looking at me and making eye contact periodically. The girls were all talking about how we acted behind my back and at one point they forced me into the lounge where he was and he stood in my way (a bit too close though) and kept asking if I was being moody with him. After a long night, I woke up in his jumper asleep on the same sofa as him and his sister was mad. WHAT DO I DO?