Heather, I’m just going to come out and say it: I like my best friend’s brother. I’ve liked him for years and apparently he likes me too, and he has for a while. But I love his sister like she’s my sister and he’s close to her as well. She knows I like him and he likes me, but I don’t think she’s ever really thought about us getting together. When she sees us flirting she gets annoyed. I don’t want to make her uncomfortable or angry. What do I do? Should I date him or forget about him?
I’m going to warn you right now that dating your best friend’s brother is probably a bad idea. Sure, there are times when it works out, but in general, I’d advise against getting involved in this kind of situation. Things can get messy fast and it becomes really easy for relationships and friendships to get ruined.
Being with your bestie’s brother can be really awkward for everyone. Your friend might feel weird when she sees you coming over to hang with her bro – but not her. She might start to feel really jealous of you two getting closer than she is with either one of you. And forget about talking to her about your relationship. Getting her involved is going to put her in the middle of things, and that’s the last place she’s going to want to be.
Think about what will happen if you and he break up. If things get messy (as breakups very often do), things are going to get seriously confusing. Even if your bestie doesn’t want to be in the middle of your relationship, she kind of will be. If there’s a lot of tension, she’ll end up feeling like she has to choose between you and her brother, and no one wants to make that decision. You also have to realize that he’s her family, and if they have a good relationship, she will probably always be loyal to him. Your relationship with her brother could put a strain on her relationship with you.
It will also be weird for you and him. Imagine going over to your BFF’s house to hang out with her and feeling like you have to avoid her brother? If you’re heartbroken over him, think about how you’ll feel when she casually mentions him. He will always be in her life, and it’s something you’ll have to learn to deal with. I know thinking about the end of a relationship before it even begins seems like a really negative way to look at things, and I’m not saying you two are definitely going to break up. But it’s important to consider this stuff before you start dating him.
If you’re still willing to give the relationship a try, then talk to your bestie. Tell her how you feel and be really honest with her. Let her know you really want her approval and you really want to know exactly how she feels about the whole thing. You don’t necessarily need her permission to be with him. But realize that if she hates the idea and you go for it anyway, it could end up messing up your friendship.
And please don’t hook up with him or date him behind her back. Lying to her in order to try to spare her feelings and make her feel less uncomfortable with things is only going to make everything worse. She’ll feel completely betrayed by two people who mean a lot to her, and she’ll be even less happy about the idea of you two being together.
If she gives you her blessing and you two go for it, make sure you keep your relationship and friendship as separate as you can. Don’t complain to your friend about her brother or complain to him about her. Make sure you make time for her as much as you’re making time for him. If she’s uncomfortable with the PDA (it is her brother, after all), don’t do it in front of her.
Just make sure you talk to your bestie before you do anything. Being honest and open is the best option here. But unless you really feel like you’re in love with him, I would find someone else.
What’s on your mind? Heather can help! Send her your question at firstname.lastname@example.org