Hi there!

Thanks for writing. First off, let me just say that serious crushes can make us do seriously bizarre things.

Still, what you’re describing is NOT cool. Going through someone’s stuff without their permission is NOT okay! You didn’t say how old you guys are, but I’m going to give him the benefit of the doubt and assume he just doesn’t know any better and really thinks James Bond spy moves will up his chances. He SHOULD know better.

Then there’s the fact that your sister is older than you guys are. You didn’t specify how much older she is, but if she’s a lot older, odds are that she’s not into him, even if he ups his flirting game. I know this, you know this, but it looks like your best friend is living in a dream world. And, dream worlds are fun…but not if they invade someone else’s privacy and/or make you feel used.

Because that brings me to this: he’s being a terrible friend to you. Like I said before, crushes can really make us do stupid things, and it sounds like this crush on your sister has gotten the better of him. Hopefully, he’ll move on sooner than later. But until then, I think there are a few things you can do.

1. You could talk to him. This kind of depends on what sort of relationship you and your friend have. And depending how you approach him, you might make him feel stupid, defensive, or embarrassed. So you should be really cautious. But you could tell him you feel like he’s only hanging around to see your sister. You could (carefully) point out that she’s too old for him and he’s wasting his energy. You could tell him he’s making your sister uncomfortable. But if talking doesn’t sound like the right approach…
2. You could set some boundaries. My grandpa tutors at a teen center and he’s always going on about boundaries. Basically it means making sure there are really clear rules about what’s cool and what’s not cool. In your case, I think the easiest way to set a boundary for your friend is to hang out with him at HIS house, or somewhere else, until he’s over this crush.
3. You could talk to your sister. This also depends on the kind of relationship you have with your sister. And she might be SUPER freaked out that some kid is crushing on her so badly, he went through her stuff. But, she might also remember what it’s like to be that age and have a crush. She might also be willing to give you guys space when your friend is over. Now, this isn’t her responsibility. It’s her house, too, and she shouldn’t have to clear out just because your friend comes around. But if she’s the kind of sister who would want to help you with this, talk to her. See what she says.

So, stand up for yourself and your friendship! But before you jump all over your friend, think about the stupid things you might have done while YOU had crush-itis.

Readers, what’s the most bizarre thing you’ve ever done or seen somebody else do because of a crush?