Dear Luv Doc,
I’ve been in love with my brother’s best friend for about five years now and I don’t know what to do about it. I started having feelings for him when I was 15 and he was 17 and getting ready to graduate. I was an itty bitty freshman at the time whose way I knew he would never look. My brother found out I had a crush on his friend when I was 17. He flipped out, saying it could never happen and that it would break his heart and his friendship if I ever did anything. Now I am 20 and he is 22 and I think I could have a real chance here. Maybe it’s a little selfish but I feel as though we’re all adults now. Should I do something for my possible relationship and maybe future marriage, or do I let it go for the sake of my possibly overly dramatic brother?
– Little Sister
I think it’s safe to say your brother was being overly dramatic, but I think maybe we should give him a pass on that. Nobody wants to think about their best friend – I am going to be gentle about this – dating their sister … or brother … or wherever it is on the gender spectrum your sibling falls … all the way up to Greg Abbott. I know your brother’s best friend might be a straight-up snack, but no matter how hard either of you try to keep it out of his face your relationship is going to be extra-cringe.
Why? Because in the back of his mind, your brother is always going to be thinking, “Is gender the only thing keeping this dude from trying to get with me?!?” Ideally, a best friend appreciates you for your mind … or maybe your sense of humor … or maybe that sweet-ass Cybertruck you drive that everyone keeps spray-painting swastikas on, but if you ever ask your bestie why they’re friends with you and they look you dead in the eye and say, “Because you are so good-looking,” it’s time to seriously reconsider your friend-vetting process. My most sincere apologies to all you people out there who secretly fantasize about banging your best friend, but … yo … that shit is creepy.
Great. Now everyone is going to think their best friend is sus – especially if they catch them in a thirsty, dreamy-eyed gaze. I can live with that. Nobody asked you to read this column. You’re a grown-ass person … or maybe an adorably precocious child. If it’s the latter, piss off, shortcakes. You can come back when your driver’s license is horizontal.
Nobody asked you to read this column. You’re a grown-ass person … or maybe an adorably precocious child. If it’s the latter, piss off, shortcakes. You can come back when your driver’s license is horizontal.
Speaking of grown-ass people, you and your brother’s best friend are exactly that. Legally you are free to engage in consensual sexual congress, even though only one of you can actually run for Congress in the state of Texas. So, if you’re really feeling it, your brother will probably get over your unsavory union eventually – surely by the time you’ve had your third or fourth kid. Nonetheless, if you will, please allow me to play devil’s advocate for a moment. Over the years, I have found that people who are romantically obsessed with their sibling’s friends maybe haven’t dated a lot of people for whatever reason. They might be extra shy. They might be isolated … by choice or circumstances … and swim in a really shallow dating pool. More importantly, as you get older it’s rare to be able to get to know someone as well as your brother’s best friend. This chap might truly seem like the pick of the litter, but let me assure you, there are some equally fantastic fellows out there who aren’t your brother’s best friend. You just haven’t had the pleasure of making their acquaintance. They also have a huge advantage over your brother’s best friend: If the deal goes south, it’s not going to ruin your brother’s friendship. That alone is worth a serious look-around. Like it or not, you’re probably stuck with your overly dramatic brother for a lifetime. I’m not trying to tell you not to follow your heart, just offer it a decent selection.
This article appears in March 14 • 2025.
