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

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

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. Today 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?

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.

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 realising 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 realise 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 behaviour. If you act weird around her, it will 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 realising 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 apologise 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 will come to you naturally. You'll be your charismatic, funny, authentic self, and that's what they will respond to.

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

Good luck.

Ask Dr Nerdlove is Kotaku's bi-weekly advice column for matters of the heart, hosted by the one and only Harris O'Malley, AKA Dr Nerdlove.

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. 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. Dr Nerdlove is not really a doctor.


    On my first skim of the headline, I didn't see the "best friend's" part and thought: what. the. hell.

    Then I realised what it actually said and went oh yeah, that's cool, what are you worried about mate? Give it a shot!

      I instantly thought of the Dare Iced Coffee ad.

      Marry your best friends sister, then your bro, will really be your bro!

      I actually had a friend joke about going out with my sister maybe semi-seriously. I said I'm fine with it as long as she is, unless he's a douche, then I'd break him :p. Then we joked about the Dare ad.

      Last edited 13/06/14 1:00 pm

    This is quickly becoming my favourite section of Kotaku - always solid advice with no BS that makes for a good read.

    People jump into the "love" claim too easy these days.

      You're so right... I think I love you.

        I love you being so honest about your feelings
        I love you.


          Oh gawd, you went and made it awkward. The article said not to make is awkward... how do we continue?

      People feel different things to you and I friend. Plus love is kinda hard to define and it is constantly changing in definition. Some people honestly think they are feeling love when what they are feeling is a crush.

        Or more literally, the desire to insert the penis into one/many/any orifice. While I don't necessarilly despise 'relationship advice' sections, they're ultimately very similar to video game reviews, subjective in the extreme. Sure there's general stereotypes you can account for as with any human interaction, but there's also no way to know if the general rule applies to situation X . There's no set win states for relationships, they're not homogenous, everybody wants something different.

        While I'm on board with the idea of helping people who are struggling, I'm not convinced such 'experts' are doing more good than harm. With a psychology background, it just makes me uneasy seeing people advised that there's a way you 'should' do something so deeply subjective, there's a plethora of ethical questions in there, especially when the advice isn't so much empirically documented from someone qualified but rather anecdotal advice.
        Either way, it keeps coming back, so here's hoping it helps more people than it hinders.

      I have a lot of love in my pants and i'm not afraid to use it.

    Maybe I'm old school but I'm all for the ol' bros over hos mentality. While I agree with most of what's been said about the situation you should still talk to your best friend first before asking his sister out or letting her know you have feelings for her. On the chance you get rejected it puts her in the difficult situation of having to keep it a secret from her brother because you're his best friend or flipside is you having to tell him you asked her out after you did which is not going to be a comfortable conversation. I would say inform him and discuss your feelings with him first to avoid alienating a close friend.

    Freaking dancing. What is it with women and dancing? Some men are just really, really bad at it, and some of us just really, really dislike it. Why must you discriminate against us? On top of which most guys I have come across who have cultivated the ability to dance really well have done so precisely because they are slightly creepy, slightly predatory types who want to use it to pick up ladies. Where do guys learn to dance well? At meat market nightclubs they went to with their dudebro mates between the ages of 17 and 25. Classic case of women wanting one thing (non creepy, non predatory guys) but then sabotaging themselves.

    As for the best friend thing - seems to me the problem with the "people don't get a veto over other people's lives" thing is this. This person is already your best friend. While a reasonable person might not regard themselves as having a veto over this situation, your best friend might well. Whether that's reasonable or not - they might. And if they do, and you don't talk to them and make sure it's all cool, then you've got trouble ahead. Some guys get very weird about their own sisters. Some guys love their mates in all their blokey glory, but then the thought of a friend turning that blokey glory in the direction of beloved baby sister freaks them the hell out. Some guys have a slightly weird level of affection for their own siblings. And almost all humans feel massively jealous when two people they have a close relationship with suddenly start paying attention to each other to the exclusion of them.

    Tread very, very carefully! I would certainly be clear with the sister about whether any date(s) will be made known to the friend at all.

      I really, really dislike it because I'm really, really bad at it.

        I dislike it because I just flat-out don't know what to do. It's like suddenly becoming conscious of your entire body and having to manually control everything.

        The only times it's ever worked were when I had some pre-learnt steps to recall (Thriller!) or when it's been a close dance with a girl, so I've basically either been puppeteered by her or been able to just follow her movements by feel. That always gives me really sore hips though :P

          Oh here's my opportunity to give advice!

          I've been a (latin) dancer for about 6 years now, and the biggest thing about it is musicality. That's basically timing... to music. And since you're on kotaku, I assume you're a gamer. That's already a big plus. So all you need to do is get a rhythm game and start messing around with that. If you can associate music and rhythm, you can dance. You can stand there and sway with the girl to the music and it's perfectly fine.

          Most/all dances have a basic that you can keep doing, and you can go into a move after that if you choose. Like A A A A A A A A A A A A A A A -> B! -> A A A A A A A etc. Certain music is more associated with certain styles(like R&B for Zouk), and stuff can get more complex, but it's just for when you feel the need to get better. Kind of like if you beat a game on the easiest setting... if you can do that, you know how to play. I get sore hips from bachata sometimes because it uses a muscle group that isn't commonly used in day to day activities.

            Better than that - I'm a musician :P And love the shit out of rhythm games.

            I can keep time to the music, that's basically all I can do. I'm standing there mentally counting the beat, but I just don't know at all what to do with it. I feel like I need to consciously decide on an action to take, but have no answers.

              Perfect! :)

              Well I think the next step is doing an intro class and/or checking out some vids on Youtube. I'm from Brisbane and a lot of places have an intro class before a party for latin dancing, and I know that most of the major cities have dance parties and they're not very expensive(even free). Like a video game, it's something that you probably won't ace on your first go, but after a few you get the gist of it and it's cake. Plus you can see how everyone else does stuff and get ideas, and figure out what styles/music you like. There's a whole lot of twists and turns you can do but it makes more sense when you develop the motor memory... e.g. hold both of the girl's hands, raise them above her head and make her turn 360 anticlockwise if you were looking top down from her, your arms are now crossed, you turn 360 clockwise(top down again) to unravel yourself to end up at the starting position. Dancing is all about having fun so if you're interested just focus on that and musicality and learning at your own pace and you'll have no probs. :)

          Yes this is how I feel as well. I'm just going to stick to the one thing I can do decently: flail my arms in a wave-like motion.

      In my experience the whole dancing thing is less about showing off your ability to dance, and more about displaying confidence in yourself. More often than not, girls tend to respond to guys that show they are confident and secure in who they are, not the ones who look like they have dancing (or leg-grinding) down to an art.

      It doesn't matter if you're the worst dancer imaginable (for the record, I'm not a big fan of dancing either). Most girls won't really care, you just need to show them you're willing to try and have a good time. Just get up there, twitch around for a while and even have a laugh at your own ineptitude. You'll be fine. Even if you dance like a rhesus monkey on crack, just being willing to give it a go will earn you way more points than being the guy sitting on his hands in the corner.

      In regards to the best friend's sister thing, I think it all really comes down to the kind of guy you are. Your best friend is often one of the most qualified people to judge whether you will treat a girl right or not, because they will be privy to the details of your prior relationships. If you tend to treat your girlfriends like trash, cheat on them, etc. don't expect your friend who knows this to approve you dating his sister, no matter how much of a fun bloke he thinks you are.

      However if he knows you're the kind of loyal, stand up guy who will treat her right, while it might surprise him at first, chances are he'll be fine with it. After all, best friends usually make for great brother-in-laws. Who wouldn't want to have their best friend at all their family gatherings?

    ACB, I know the feels!
    I have a great friend and we went through the entirety of high-school together. A few years after High-school I started to get to know his younger (by 3 years) sister a bit better and found out that we were both really into each other. She was still completing the HSC so we decided to hold off until after her studies, I spent those 4 months really getting to know her as a friend first and that was a great experience I wouldn't trade for anything. As to talking to her brother and my friend about it, well, I agree that the best solution is to be direct and confident. There was a good respect between the siblings and so when I talked to him about it he was totally fine with me dating her, he gave me a smile and said 'just don't do anything to hurt her'. 2 years of wonderment later and I feel like I have even grown closer to my friend because I am dating her.
    You can do it man, just be confident and stay open and honest.
    Good luck :)

    Had a coworker/friend telling me semi-regularly about her sister, and one time I joked, "Yeah, she's pretty hot. She single?" and next thing I know I've been handed her number, some photos, and a recommendation for a date.

    It didn't work out. For one thing, the little sister was just SO similar in appearance, speech, and mannerisms to the coworker/friend that I was greatly unnerved most of the time. Didn't help that I was pretty sure (and later vindicated) that the coworker was into me, despite having a long-term boyfriend. Ended up opting for neither.

    All the same. You might be surprised by how OK with it the friend might be.

    Last edited 13/06/14 5:54 pm

      You totally missed out on your opportunity for some sister on sister threesome action dude!
      Guys dreams are made out of these things! :P

    Did this (minus the overseas part) - Didn't tell the mate but things didn't get too serious and I moved on to meet my current GF :)

    Like the article says though - don't jump the gun by telling your mate before its even 'real' - Find your way if things do get serious and you do believe she is right for you then tell the mate.

    Depending on the culture of the family I would say the best friend/sister situation would b opposite. Highly suggest telling the bro you felt a spark and if its ok to pursue it. Whether it is right or wrong to ask someone for permission first, it can look like your going behind their back(which is what happened).

    I've never had any of these problems. None of my friends have sisters, or if they do, I very rarely meet them. I've also never been to a wedding.

    Huzzah for a sheltered life.

    I'm not in love with my best friend's sister but my best friend likes my sister and went behind my back about until I forced it out of him. And now, even though I have been told by her close friend, my sister constantly lies about liking him back. I have countlessly asked her if she does but every time she has lied about it. I eventually went through her phone and found a lot of shit. He gave her my phone passcode after she asked for it and he has asked her to check my phone for some messages and they go on and on with flirting.

    Here's the kicker: He's a senior in high school and she's in the 8th grade.

    What do I do?

Join the discussion!

Trending Stories Right Now