Lovehacker: Should I Date My Best Friend?

Lovehacker: Should I Date My Best Friend?

Dear Lovehacker, I’m a hetero male who has experienced the full dating spectrum – hook ups, kinda serious, and very serious. I’ve dated women who were more attractive than me, less attractive, more intelligent, less intelligent, emotionally abusive, exes of friends, the whole spectrum basically. I’m at a point where I feel like I know what I like, know what I dislike, and think of myself as a pretty flexible person with reasonable standards and boundaries.

Lately, I’ve been suffering from a case of the ‘I don’t want to die alone syndrome’. Whenever I get this feeling and think about my dating lessons and failures in the past, my mind always wanders to my (female) best friend.

We have known each other since we were teenagers and we are best friends in the true sense, always there for each other, similar sense of humour, similar interests, etc. Any amount of time we don’t talk or see each other doesn’t damage the friendship, we really get each other on the most fundamental level and that seemed to be the key lacking in the ghosts of relationships past.

So where is the problem you ask? I don’t find her attractive. I can say objectively she is a very pretty woman, guys are all over her, but I just don’t see it. I love this person and personality wise I could not dream of asking for more, but in all these years I’ve never stayed up late at night fantasising about her or lusting after her. Now I know that no relationship will give you everything you want, and I was wondering your take on this high-stakes mission I am contemplating. Might the attraction grow, does it even matter, is there some other latent reason I’m not acknowledging her hotness that everyone else seems to see?

The other problem is I don’t want to ruin things and mess up a friendship that is 20 years old, especially on something I’m kind of divided on myself. It’s not just that she might not be feeling it, what if she is and then I’m not? What if we try and end up ruining the friendship? I’m confused as hell here and need some advice Doc – I don’t want to die alone, don’t want to be too stupid to see what’s in front of me, and don’t want to mess up the most meaningful friendship I’ve ever had. Thanks, Not Feeling It

Dear NFI,

There are a couple angles to this. So let me start with the obvious:

Why does your relationship with your friend need to be romantic? You’ve been friends with her for decades now and have been satisfied with your relationship as it stood. Going by your letter, there’s never been any frustrated sexual tension, nor have you suddenly gotten a bad case of feels for her… you just feel like you should be in love with her.

The thing is: there’s a lot of cultural bullshit surrounding male and female friendships – the ever classic “men and women can’t be just friends because sex always gets in the way”. It’s not just insulting to men in general – implying that we are both emotionally stunted and at the mercy of our genitals – but devalues friendship in general. Friendship is amazing; a lifelong, intimate friendship like you and your BFF have is even more so. She is, in many ways, your family by choice. That’s valuable in and of itself without having to add love and sex to it.

But let us assume, for a second, that you’ve decided to take a shot at dating her. Let’s game it out a little, because there’s going to be one critical issue in your relationship with her and that’s going to make or break the two of you as a couple.

How do you feel about sex? Are you OK with not being sexually satisfied for as long as the two of you are together? Because if sex is important to you, then you’re basically dooming your relationship with your BFF. Just going through the motions of erection-to-ejaculation doesn’t mean that you’re going to enjoy it. You may clear the pipes, but it’s not going to be that same dopamine and oxytocin rush or that giddy feeling of intimacy and affection.

Then there’s how she feels about sex – even if it’s not important to you, it very well might be to her. How would she feel if she knew that your trying to keep her satisfied was the sexual equivalent of “taking your vitamins” – something unpleasant but necessary? That’s going to hurt, on a deep and primal level, and that pain can damage the core of your relationship.

Now to be sure: not every romantic relationship needs to have a sexual component. There are asexual people who have romantic relationships. There are couples who have companionate marriages, or whose union is about love and affection and companionship and where sex isn’t as important. Those are just as real and valid and happy than relationships where sex is important. But that doesn’t seem like what you’re looking for.

Ultimately, I think you’re borrowing trouble when you don’t need to, NFI. I think that you’re letting your fear of being alone — an understandable, if not terribly logical one — get to you. The fact that you’re in a relationship doesn’t mean you won’t still die alone. Relationships, after all, do end — either in a break-up or in death. Even if you and your best friend were to make it last “forever”, there’s no guarantee that you’ll die in the saddle before she does.

And more importantly: the fact that your relationship with her isn’t romantic doesn’t mean that you’re alone. You’re both incredibly important people in each other’s lives. You’re family in all but blood. That’s pretty damn rare and incredibly special. Don’t devalue that love just because it’s not the hearts-and-flowers-and-cartoon-birds kind.

TL;DR: I don’t think pursuing a relationship with her just because you don’t want to be alone is a good idea. Work more on that fear and let your friendship be what it’s going to be, without trying to push it into something it’s not. Trying to force it into a new and different shape is going to damage things more than a love that happens organically.

Good luck.

Lovehacker is a weekly relationship and sex column where our resident Agony Aunt answers your questions. Need help? Drop a comment below or email [email protected].

This story originally appeared on Kotaku.

Harris O’Malley is a writer and dating coach who provides geek dating advice at his blog Paging Dr NerdLove.


  • I normally cringe at these articles.. the ‘dear martha’ style is just a little bit out of sync with so much else on this site.. but I have to give you credit where it is due.. and this is a balanced and sensible response to a rather nuanced question.

    I have just had a 20yr intimate relationship with my best friend end rather unceremoniously.. and your comment “the fact you are in a relationship doesnt mean you wont die alone” resonates with me on a very scary level, since I share the same “understandable, but not entirely logical” fear..

    So in a rare case of me actually agreeing with something on the internet.. I want to say to NFI.. appreciate what you have and cling to it for all it is worth.. but be OK with being alone, since you will never know when you may end up back in that state with no other obvious alternatives staring you in the face..

  • I’m surprised there arrogance of the op wasn’t touched upon. Just because he decides that they could date would mean the BFF would surrender at his mercy? What if she didn’t want a relationship? Thought ever occur?

    • The conversation has to come up at some point in some way. Being that the letter was from the guy’s perspective, he just threw it out there. I’m sure he’s aware that it takes two to tango.

  • I know that intimacy can change the dynamics of the relationship and create expectations and pressures that didn’t exist before.

  • Another thing to consider in the psychology between you and your friend is whether you see things as being even or equal. The fact that you don’t find her sexually attractive, but still acknowledge she IS attractive says a lot about your familiarity with her. Perhaps you don’t treat her as romantic interest, but more, as a sister. As an example of psychology shifts in relationships, a lot of toxic, abusive relationships turn from equal positions of ‘lovers’ to unbalanced positions of ‘parent’ and ‘child’ where there is little respect, or dependence on another. The balance changes… so be aware of your balance with your BFF and consider whether you are the best match for her, she for you, and if she’s not just an easy target for you because she’s simply just… there.. in front of you. Maybe speak about it with her openly and honestly and show that vulnerable side and you will hopefully get an honest response back.

  • i married my best friend.
    the sex and attractiveness should come out of the love you have for each other imho.
    if you are looking for lust, you will never be satisfied with one woman because there is always someone more ‘attractive’ out there.
    love is about commitment and commitment is about choice. love is not a feeling, it is a choice. if you have a sense of humour similar to hers and share similar interests and you get each other – thats the perfect start for a romantic relationship – you both have to want it though and you both have to be willing to actively work at it too.

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