I'm in love with one of my best friend's older brothers. I have known the family for years and have always thought he was cute. He is currently separated from his wife, and I also just became single. I've been seeing him out a lot more often. We hooked up once after a night of drinking, and I get the vibe that he wants us to keep seeing each other. I haven't told my best friend, and I'm worried she'll be pissed. Whenever our friends have said her brother is cute, she's rolled her eyes and seemed annoyed with us. What should I do? I want to hang out more with him but don't want my friend to be pissed at me. Maybe he should talk to her about this, and not me?
Hooking Up With My Bestie's Bro
Dear Hooking Up,
I get that you like this man and have been pining for him since middle school, but he's part of your best friend's family. That can be touchy for some people. Be aware that this might not have the happy-ever-after sort of ending you're hoping for.
You should have told your friend that you had feelings for her brother. Maybe she suspected you had the same sort of superficial crush that all the girls on your soccer team did, but it's too bad you were uncomfortable sharing your true feelings. If you do end up in a serious relationship with him, your girlfriend might feel like her two worlds are colliding. It could take her some time to warm up to the new arrangement. And the fact that you started hooking up with him without her knowing might feel like a double blow.
Get the first one over with and tell her right away. Your friend might be upset, but the sooner you tell her, the sooner she can begin to get used to it.
However, if she's really not down with the relationship for some reason, you'll have to decide what's more important to you: fulfilling the romantic fantasy or keeping the longstanding friendship. Good friends are hard enough to find, but true romance is even harder. Which would you regret losing more? Only you can answer that.
Don't leave it for the bro to sort out. Your friend needs to hear from you. He's not responsible for your friendship, and you don't need to wade through whatever family stuff is going on.
It's also time to talk honestly with this man, if you really like him and want to explore a real relationship with him. Find out what he's thinking and feeling. You said he's recently separated; does he long to reunite with his wife, or is it truly over? Either way, these feelings are fresh and he might not be ready for something serious just yet. Then again, maybe he's been fantasizing about you all these years, too. There's only one way to find out: communicate.