Ask Dr. Nerdlove by Harris O'Malley

Is It OK to Date Your Best Friend’s Sister?

DEAR DR. NERDLOVE: I need some advice. You’ve said before that, when asking someone out, no one gets to call dibs, just because another person dated them first doesn’t mean you can’t now, etc. The general gist of what I got from this is: the only people that matter are you and her, nobody else gets a say in whether you date her.

But what what about a sibling?

I’ve recently been spending some time with the sister of one of my good friends (I’ve known him for about 5 years, and just met her a couple months ago). And I think she’s pretty awesome. And she’s attractive. So, of course, I’d like to ask her out.

Obviously, if we were to start dating, we’d have to tell my friend. But, should I consult him first? How would I even begin that kind of conversation?

Any suggestions you can give me on this would be awesome. Thanks.

– Bro Fist

DEAR BRO FIST: Dating is not a democracy. Unless you’re already in a relationship (in which case, different rules apply entirely) other people don’t get a say in your dating life. Period. They are allowed an opinion – and most of the time would do well to keep it to themselves – but not a vote or a veto. End of.

Now, this doesn’t mean that dating is consequence free as a result. When you’re dating a friend’s ex – or in your case, a friend’s sibling – then things can get complicated. There IS the possibility for hurt or complicated feelings, and that CAN put a strain on your friendship. These are some of the risks you take, and you have to be willing to do the math and decide if these risks are acceptable to you.

Are you obligated to consult him first? No, not really. This is the 21st century; his sister isn’t his property and she’s free to date whomever she damn well pleases, whether he likes it or not. You hardly need his permission.

(Hell, I don’t even like the idea of asking a woman’s father for his blessing to propose to his daughter. Giving a heads up? Sure. Asking permission or for their blessing? Not as much.)

All that being said, your buddy may well not be cool with your dating his sister for any number of reasons. Presumably he knows you better than anyone else; if he knows you’re a horndog, he’s not going to appreciate the idea that you’re trying to work your way into her pants – never mind that she’s capable of making her own decisions. He may worry that you’re going to hurt her or that she may hurt you. Or he may think it’s cool, he may think that she’s a grown-ass woman who can handle her own affairs, or he may not give a damn one way or the other.

Thing is though: his opinion on the matter is your secondary concern. You should ask her out before you worry about what he thinks. No point in getting all worked up if li’l sis turns you down flat.

Do you NEED to consult him? No, not really. Should you give him a head’s up? Yeah, it’s good manners and you don’t want to seem as though you’re sneaking around behind his back; that’s a great way to destroy a friendship and possibly catch an ass-beating in the process.

I’m not saying that it won’t be a tricky situation; some brothers are extremely protective of their siblings, especially if they’re younger. Pull him aside and tell him him that hey, you and his sister are really starting to hit it off and it seems like the two of you might have something good going and you wanted to let him know because you’re his friend and you respect and care about him. Be straight with him, be respectful… and for the love of GOD don’t make any sort of even vaguely sexual jokes about her. Again: great way to catch an ass-beating.

Good luck.

DEAR DR. NERDLOVE: Long time reader, first time writer. My question is simple, yet I think I would benefit from some of your insight.

I’m a guy who started taking singing lessons a few months ago, just to expand my musical repertoire. I was surprised to see that all the other students are girls roughly my age (early-to-mid twenties), and with similar interests. Just to quickly clarify, the lessons themselves are private, one hour sessions, with the same teacher. This means that by the time one of us is done and leaving, the other is just arriving. I guess you can see where I’m going with this.

Long story short, I would like to ask one particular girl out who is scheduled right after me. Just a quick coffee date to get a chance to know her better, since she’s incredibly cute and I know for a fact that, aside from singing, she also plays bass which is just awesome on so many levels. The problem is that there’s really no appropriate time, or way, for me to do this. 

The only time I have to talk to her is when I’m leaving and she’s arriving, which not only is usually less than a minute, but is also incredibly inconvenient, considering we’re all on a tight schedule and asking her right before a lesson would put her in a position where she has to answer real fast, and in front of our teacher. It would feel less like an actual “move”, and more like  a cheap trick to pressure her into saying yes as quickly as possible. 

I could ask her number from said teacher (who has our contact information), and ask her out that way, but there’s no way to do that and come off as anything, but a giant creep whose only in it looking for some tail. It feels rude and spineless, and frankly I’d rather do it in person. 

The best option I could come up with was to finish my lesson, go into the nearby café that’s literally 10ft away, order a cup of tea (earl grey, hot), wait an hour, and ask her after she finished. While I can see this as something “cute” and safe, since she’s no longer pressed for time, or in an “official” environment, I also realize the stalker aspect in such a move. I guess I could say that I “just happened” to have had some business around  there, but I’ve always found these “fabricated meet-cutes” to be dishonest and cowardly.

So my question is, do you think it’s acceptable to “camp out”, so that you may talk to someone at a more appropriate time, and if no, I would greatly appreciate some advice.

Cautious Approach  

DEAR CAUTIOUS APPROACH: Sweet Zombie Jeebus, CA, don’t camp out and ambush her. That’s a great way to come across like a creeper even when your intentions are entirely aboveboard and honorable.

While we’re at it: trying to get her info from your teacher? Lean in a little closer, I want to make sure you get this:


And also: NO!!

F--k me running, it’s a good thing your instincts are telling you that’s a bad idea. Yes, trying to weasel her info out of her teacher is pretty spineless. It’s also even bigger stalker behavior, potentially illegal and a huge violation of your crush’s privacy — and that’s before we even get to the part where you’re trying to convince a bystander to betray her trust in him. And what the hell are you going to say to her when you call her out of the goddamn motherf--king clear blue sky? “Hey, remember me, you have voice lessons right after me. How’d I get your number? Hey don’t worry about it, it’s no big deal so are you doing anything tomorrow? Hello?”

If you’re really lucky, you’ll only have ONE restraining order to deal with.

The best thing you can do is ask her yourself, in person, when you see her. It doesn’t have to be high-pressure at all. Leave a little early, so you can catch her before she comes into the room – that way it won’t feel like an ambush, more of an idea in passing. Relax, give her a friendly smile and say “Hey, you know what? We see each other almost every day and I barely know anything about you, but you seem like you’re really cool. If you’re interested, I’d love to buy you a cup of tea after class and talk music.” Short, simple, to the point. If she’s down, tell her you’ll meet her at the cafe. If not, then you shrug, smile and say “Ok, cool. Have a good lesson!” and roll on like all she said was “yeah, I think it’s going to rain this weekend.”  Next time you see her, it’s business as usual. You can do your “Mornin’ Sam / Mornin’ Ralph” routine as normal.

If you don’t treat it like it’s a big deal, she won’t treat it like it’s a big deal. You’re asking her to meet up for tea and friendly talk, not to bear your children.

Good luck.

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