I have this friend, and she has a brother who is two years older than me. I like him, and she knows that and he knows that. Every time I see him I get really nervous, and when he talks to me, I am shy. He always asks me why I'm sad. We tease each other, and everyone thinks we're flirting, but I don't know. If he does ask me out, should I say yes? My friend seems pretty nice about it, but I just don't know. Please help me.
This One Girl
Dear This One Girl,
I think we've all liked someone we thought we shouldn't at some point. A good old-fashioned crush on your friend's brother is perfectly normal. Flirting should be fun, but you seem stressed, and no wonder: Your female friendship is standing in the way of your potential romantic relationship.
Have you asked your friend how she feels about you dating her brother? She may seem cool with it because your flirting is so innocent — but her feelings could change if you two got serious. Or maybe she's used to her friends having crushes on her sib. It's time for a heart-to-heart with her to find out.
Be direct about your feelings for him, but reassure her that you value your friendship with her. Ask what she thinks of you taking the flirting to the next level. Would she mind if you went on a date with him?
She may think you dating her bro is a great idea. Or she may not, and you'll have to decide if you want to respect her wishes and give up the fantasy of getting the guy — or pursue him at the expense of your friendship. Don't be mad if her answer is no; you're the one asking for her honest opinion.
If she gives her blessing, why wait for him to ask you out? Do it yourself! He might be nervous about the sister issue, too. If you make the first move, he'll know everything is copacetic.
Maybe you ask him out and he says no. It'll be embarrassing, but at least you'll know where he stands and be able to move on.
If he is down with dating, you'll have to be mindful of the discomfort that can come with seeing your bestie's bro. Telling your gal pal every little detail, or asking for her advice, may be crossing a line. And if your relationship turns out to be a complete disaster, she may have a hard time balancing the feelings of her friend and her brother.
Be prepared for any of these scenarios. But it doesn't mean the relationship won't work out beautifully. You'll never know unless you try.