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​Ask Dr. Nerdlove: I'm In Love With My Best Friend's Sister

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Hello Internet! Welcome to Ask Dr. NerdLove, the only dating advice column that's short on bullshit, tall in wordcount, narrow of purpose and wide in vision.

First, a tangental note. If you're a fan of fine gaming podcasts, then you might want to check out this week's episode of Rebel FM; I'm joining Anthony Gallegos, Arthur Gies and Mitch Dyer for a special all-relationship-questions episode.


But today on Kotaku, it's all about walking the line between being the cool guy and the pushy jerk. What do you do when you're in love with someone… but making a move might violate bro code? And what's the best way to try to hook up at a wedding without doing your best Vince Vaughn impression?

Let's do this thing.

Hey Doc,

I've been a fan of your friendly but stern advice since I first read your column but to be honest I never dreamed I'd write in. I have a problem concerning the friend zone but not the "I am inserting friendship when does the sex come out?" kind of friend zone but the real messy kind. You see I have a best friend (a guy best friend) whose little sister has been hanging out with us since we started hanging out. She seemed really tomboyish at first but my friend and her left the country for a while and the only way I talked to them was through messages. Eventually we started really talking and she opened up about some things in a way I'd never expected. I know it sounds cliche but I think I'm in love with her.

And once again to clear things up, not the "She's so beautiful inside and out! I must own her!!!" kind of love but I legitimately care for this girl and I'd like her to be involved in my life for as long as possible. Problem is her brother is my best friend. I don't think that's fair to him, and that's not even mentioning the fact that she might not feel the same. She still is tomboyish and the threat of a relationship/romance could alienate her. If possible I'd like to be closer to her but I don't want to risk losing these relationships because they each are a really big deal to me.

Thanks for reading,

Average Crate Box

Believe it or not, this is actually a common occurrence, ACB.

There's an interesting quirk of the human psyche known as the Exposure Effect. The more times we're exposed to something, the more familiar it becomes and the more we like it. This is why marketers hypersaturate the airwaves with specific commercials and why that annoying song you hear on the radio all the time starts to become a guilty pleasure that you kinda dig.

And it's why when you get to know somebody and spend time with them, they become much more attractive to you.

You've been spending a lot of time with your bud's little sister and now you're realizing hey, she's actually really kind of hot and awesome.


But you need to take things one step at a time here. First things first: until she's back in the country, it's kind of a moot point. Long distance relationships are tricky enough as it is. Long distance relationships that start long distance and have the added drama of bro-code and the uncertainty of whether she's interested in you

Yeah, that's not something you're going to want to pursue. This is a situation that's best handled in person.


But let's imagine for a moment that you weren't having to deal with the long-distance issue.

I realize you're stressed about how this might affect your relationship with your best friend, but honestly? That's putting the cart before the horse here. Before you worry about how to tell him that you think his sister's hot, you should at least take time to find out if his sister is even interested in you. And the best way to do that is, simply ask her out on a date.

Don't hem and haw or roll it out like it's something bad, or that this is you should be apologizing for. And for fuck's sake, don't do the "ha ha just kidding… unless you're serious" routine. Just lay it out there. "Hey, you know what? I think you're awesome and you're a great friend and I'm glad we've been getting close. And to be perfectly honest, I like you and I'd like to take you out on a date. Feel free to shoot me down, I'm going to be totally cool about that. Either way, I think you're cool to hang out with and I'm super-happy that we're friends. "

If she's into you: awesome. Go on a few dates, see if this relationship's got legs or not. If she isn't though… then you respond as though it's no big deal. The key to not making things awkward is simply to be cool with it. She says "no" or even "Dude, you're like my older brother!" then you shrug your shoulders, say "Ok, cool," drop it and carry on like normal. If she needs space for a bit, give it to her. Say "I understand, I'm around if you want to talk." Don't pretend like it didn't happen - that's it's own kind of weirdness and can make people uncomfortable. Just don't react like her rejection changed anything or treat her differently. People will take their cues from your behavior. If you act weird around her, it'll get weird. If you treat it like it's no big deal, people will take it like it's no big deal.

Now where things get complicated is in talking to your best friend. There are a lot of competing ideas over whether to talk with him first, whether to give him the heads up or whether to ask his permission first.

While I can see the different points of view, I'm of the opinion that people don't get veto power over other people's relationships. His sister is her own person with her own interests and desires; telling her that his feelings outrank hers is a shitty thing to do. He doesn't get to control her dating life.

Now, all that being said, you should talk to him, at least to give him a heads up. Again, I'd say that a head's up isn't necessarily warranted unless and until things are starting to get serious; if you two just go on a date or two before realizing that it's not really going to work out, then you've invited a lot of excess drama for no reason. But if it's looking like you two might have an actual thing, then you do want to tell him. And again: you lay it out like it's no big deal. "Hey, I just want you to know: your sister and I've been talking a lot lately and we've been getting pretty close. We think we've got something good going on and I wanted you to know so this doesn't come completely out of the blue."

And then the ball is in his court. He might be totally cool with it. He might freak the flying fuck out. He might be weirded out because of the way the two of you have had mutual discussions about all the ways you want to get your freak on with different women and it's completely different when it's his sister, man. He may just to keep things on a need to know basis and knowing that you and his sister might be having sloppy make-outs is very much a don't need to know.

(And also: if you do date her, dial the PDA way the hell back around him. There's some things folks don't necessarily want to see and that includes their siblings sucking face.)


You may have to have a long talk with him. You may have to weigh whether your interest in his sister is more important to you than your relationship with him.

But - like I said - his sister isn't his possession; she's her own person with a right to date whomever she wants. And honestly? If she is interested in you back and there is relationship potential there, then everyone will need to put on their big-kid pants and deal with it.

Hey Doc,

One of my dearest friends is getting married in July. She's someone I actually once had feelings for but Nice Guy'd it (without all of the blame and resentment, I knew it was on me for not making a move.)

We are from very different social circles so I don't have any familiarity with her friends, but she told me that she has talked me up to all of her single friends that will be at the wedding and has even gone so far as to seat me with them. Apparently many are excited about the prospect of meeting me (if not more, by the way she stated it.)

The problem is, I don't have a lot of experience in "picking up" strangers. I have had relationships, but those were built over long periods of time and just sort of happened. I am generally positive, funny and kind of charismatic but I also deal with anxiety issues, especially in high pressure situations.

I'm not really looking to sleep with one (or all) of them, but it would be nice to come away from the night with a few numbers or at least knowing that I didn't screw up a situation that was laid out perfectly for me.

I apologize that this sounds kind of douche-y, but it is a legitimate concern for me. What is the best way to approach this without ending up looking like a jerk (which seems entirely plausible when surrounded by seven women who are all close friends), or worse, a coward.

Honestly, I just want to have a good time. My friend is very sweet for trying but I feel like she's put me in a no-win situation.



Single's Table

Dude. Dude. This is the opposite of a no-win situation. Your friend has gone out of her way to set you up with the easiest, lowest-risk, most softball scenario you could possibly ever encounter. You are in a prime position to have an amazing time, regardless of whether you hook up with someone or not.


To start with: She is putting you in position where you will be meeting people you know are single. On top of that, she's doing so at a wedding, an incredibly emotionally charged event. Wedding Crashers ain't entirely wrong: weddings are prime territory for hook-ups because people are there to drink, dance and have a good time. It gets people excited and that excitement turns into arousal very easily.

Moreover, you've got your friend talking you up to these women; this is the best possible form of advertising short of having an ex-girlfriend vouch for you. She is providing you with what's known as "social proof" - that is, she's demonstrating that you're coming pre-vetted as a cool guy and someone they should get to know. To put it another way: she's the warm up act getting everybody in the mood to have fun and eagerfor you, the main act, to come and take the stage.


And all you have to do is just relax.

Seriously. Your friend has done most of the heavy lifting. All that's left for you to do is just have fun. You don't have to be Studly Good Night or the life of the party, you just need to enjoy yourself, and be a fun, social guy and at the end of the night, tell one of them (or all of them, really) "Hey, I had a great time meeting you tonight and I'd love to see you again."


Easy as can be.

Now the three best tips I can give you? First: go easy on the booze. It's tempting to throw a drink back to ease those nerves. Then a second one because you're not entirely sure the first one worked. Then a third because you're pretty sure the first two got lost on the way to your stomach and you need to send out a search party. Then before you know it, you're the sloppy drunk guy giving the embarrassing toast that leaves everyone cringing and praying for it to end.

Second: dance. Dance with all the ladies. Being the guy who's willing to dance at a wedding will, hands down, make you the most popular man at the entire reception. You don't have to dance amazingly well (although it certainly helps); you just have to show you're willing to go out there and have fun, rather than being dragged out on the floor.

Third: be outcome independent. The more you focus on trying to get laid or even trying to get phone numbers, the more you're going to tense up. Putting all that emphasis on a specific result (i.e. hooking up) will leave you feeling like you have to "perform". You'll be creating a high-pressure situation (where there really isn't one) and end up triggering those anxiety issues.

But if you just focus on getting to know these people, connecting with them, finding commonalities and generally just having a good time, it'll come to you naturally. You'll be your charismatic, funny, authentic self, and that's what they'll respond to.

Go. Have fun. Relax. You'll do fine.

Good luck.

Have you ever had your relationship run afoul of bro code? Ever have a crazy hook-up at a friend's wedding? Share your thoughts and stories in the comments section, and we'll see you in two weeks with more of your questions!


Ask Dr. Nerdlove is Kotaku's bi-weekly dating column, hosted by the one and only Harris O'Malley, AKA Dr. Nerdlove. Got a question you'd like answered? Write and put "Kotaku" in the subject line.

Harris O'Malley is a writer and dating coach who provides geek dating advice at his blog Paging Dr. NerdLove and the Dr. NerdLove podcast. His new book Simplified Dating is available exclusively through Amazon. He is also a regular guest at One Of Us. He can be found dispensing snark and advice on Facebook and on Twitter at @DrNerdLove.