Ask Dr. Nerdlove by Harris O'Malley

I Have A Crush on My Best Friend’s Sister. What Do I Do?

DEAR DR. NERDLOVE: I’m trying to figure out if I like my best friend’s sister and if she likes me back. In other words, I’m trying to see if it’s worth the pursuit. I don’t get to see much of her often but I think about her more than any other girl; I’m introverted and shy so I don’t keep in touch with a lot of my girl friends all that often. Oddly enough, I’ve known her since I was 12 and she just was eight years, I’m 25 and she’s now 21. I’ve kept in touch with her longer than any girl I’ve ever known. I definitely understand that a lot of this might just be that I’ve never been with anyone before and since I’ve known her the longest, I think I can certainly trust her if our relationship develops into passionate one.

One of the things stopping me is that her brother is protective of her. I completely understand this, but frankly, she is old enough to make her own decisions. Also, I think if she was interested she might’ve given me better clues. Although to be honest, I would guess she’d know me well enough to know that I would be very intimidated to start dating the little sister of my best friend.

Since I’ve discovered I had a crush on her, I’ve gone to the trouble of mentioning she looks nice, that I noticed she changed her hair, stating I was shocked she didn’t like how she looked, etc. Sometimes, when we’re all drinking altogether I’ve made sure she gets plenty of water and just makes sure she’s all right. Her stepmom has even commented that I would be a good match for her based how I treat her. However, I think it more like a carefree joke… and I was so embarrassed that I couldn’t say anything.

I’m just not sure how to go about talking to her about this; not just because of her protective brother but because I’m often a bit more sarcastic and I worry she might not take me seriously. If it’s just a simple crush do I even say anything? If I say anything to her about it, do I risk losing my best friend? Maybe I’m reading too much into this but she’s been dating a lot of guys who are ofter shyer than me and even some have looked a bit like me. She does go out of her way to introduce me to her boyfriends and they do seem to be a little protective, almost like they’re jealous. (If I knew better, I’d suspect it to be very Aaron Sorkin-esque relationship.)

Based on how complicated things are, I’ve been trying to meet other people. I’ve made a point to talk about other girls that I’ve gone on dates with and how I wasn’t very compatible with them. On just the couple of occasions that I’ve talked about girls she’s been strangely silent, even to the point where she actually leaves without a word. Her only advice was that she could see me with someone as young as 20. With other friends in our circle she’s a bit more curious how certain things have worked and what didn’t.

I’m trying to figure out if there’s something between us but I worry about what my best friend would say if he found out… I don’t know who to talk to about this stuff.

Stumped Over Sibling

DEAR STUMPED OVER SIBLINGS: Can we cut the bulls

t a little, SOS? Because between you, me and the entire Internet, it’s pretty safe to say you’re interested in your bro’s sister. You don’t need to keep hemming and hawing and throwing conditionals in there to make it sound like you’re not sure if you’re into her or not but you THINK you might be but…

Just be real here. Your buddy’s sister got hot, you have a thing for her. It happens. And that’s fine, man. You’re both adults. The fact that you’ve known each other all this time doesn’t preclude you from recognizing that she got cute, nor does it mean that she’s off limits because you two grew up together. It’s not like you’ve spent all this time waiting for her to come of age. You both grew up, you matured, you changed and now you’re starting to see her as an adult woman instead of an adjunct to your best friend.

So it’s not that you don’t know whether or not you’ve caught feels for her. It’s the potential for unnecessary drama you’re worried about that makes you hesitate to declare that yes, you’re into her.

But before you worry about your buddy, you should decide what you’re going to do about HER. After all, she’s the one you’re interested in, so she’s the one who’s going to be the one to decide whether or not she’s interested in you, too. If you’re interested in her, you should probably find out how she feels before you worry about literally anything else.

And to be perfectly frank, running to her brother for permission is a wee bit patronizing. Doubly so considering that she’s a grown-ass woman. Family is family and they certainly get to have an opinion, but they don’t get veto power – either overtly (“No, you can’t date him, sis”) or by fiat (“Talk to my sister again and I’ll kill you”) over her love life. So if you’re interested in her and want to try to pursue something with her, then maybe you should run things by her first before you worry about her big bad bro.

Of course, you’re not sure how she feels about you. You think you’ve been getting some hints, but the ol’ Magic 8-Ball keeps coming up “Signs Hazy, Ask Again”. So what do you do?

Well, the way I see it, you’ve got two choices. You can spend weeks and months trying to read the tea leaves and divine her intentions from subtle little things that may or may not mean anything. Or – and stick with me, this is a little crazy – you could always ask her out on a date.

Extreme, I know. But it’s a fairly reliable way of finding out if someone wants to date you.

If the two of you are into one another and you’re going to pursue this more than just the odd date or two, then you can worry about her brother. It’s entirely possible that this would be something he couldn’t possibly tolerate and it’d put a strain on your relationship with him. At that point — and not before — would you have to decide which is more important: your friendship with him, or your relationship with his sister.

But if he’s your friend and he knows that you’re a good guy who would be good for his sister, then that shouldn’t be as much of a conflict. It could be difficult if he does have a freak-out – especially since that’s insulting to both you and his sister. 

But as I said: he doesn’t get a veto.

Good luck.

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