Yes, Virginia, You Can Date Your Best Friend You’re Secretly in Love With (At Least, In Theory)

In an age where the only coping mechanism many of us can afford, financially or spiritually, is “detached irony” I think we all have a few tweets that keep us up at night with the searing truth they forced us to briefly confront in 280 characters or less. This is one of mine, although I can’t be sure whether it originated on Twitter or Tumblr and any initial mention of it seems to have been deleted from Twitter. (~*x files theme*~) The substance of it as follows:

Straight Dating: We have been talking for a few months and I think we are officially going out
Gays Dating: This is Adam I met him 2 hours ago at H&M and he is the one 🙂
Lesbians Dating: We have been best friends for four years

Although I will allow the gay male denizens of H&M to speak to the veracity of this for them, and although I am not a lesbian per se, this truly leveled me. (Are they… even dating now? Do they know???) I started thinking about how often we discuss the prospect of staying friends with an ex — a topic extremely deserving of discussion! — but for queer women, it feels like we’re just as likely to be dealing with the dilemma of dating a friend. There’s not much of a template out there for how to navigate it! This probably won’t be one either (just managing expectations!) but we can talk about some things to know!

Should You Even Do This? Can You?

Having fielded years of queer women’s dating advice questions through this job, I can tell you that by far one of the most common questions is a variation on “I’m in love with my best friend; should I tell her?” (There’s a subcategory of this question wherein the best friend is straight; I’m not going to address that here because unfortunately I have nothing to offer you but prayer.) Your needs are better served here and here. There also isn’t a lot I can tell you even if your bff isn’t straight — the answer to ‘is this a good idea?’ hinges very heavily on whether your friend reciprocates your feelings, and neither you and even less I have any way of knowing that. As for questions of how it will change your friendship — in either scenario, whether she’s also into you or not — this is also not really a factor you can plan for. You might be able to work through it if you’re on different pages and get to a really healthy place and it could make your friendship stronger; it might also not be something you can ever really return to a time before. Even if you (and your friend!) think you know how you would deal with that eventuality, you could be wrong; we surprise ourselves. (I am thinking of this most recent dilemma in Ask A Fuckup.) We often hear readers say “I’m worried about ruining my most important friendship,” and that’s a valid concern! If this friendship as it stands is something you can’t live without, then you’re right, risking it changing might not be the best move for you. Unfortunately most of the big decisions in life are ones we have to make without knowing if they’ll work out. The decision about whether to Go For It with the friend you’re head over heels for is one you will have to make mostly on your own.

However, what I can tell you is:

People Definitely Do This

To source input for this article (as someone with at best a light history of dating my best friends), I put out a casual ask on Twitter for people to email me if they had done this before and wanted to share. Reader, within a few hours I had 40 people get in touch with me. As of the writing of this article, I have lost count and have had to stop responding to people who write in because it’s unsustainable. Y’all have a problem! Regardless of the larger questions about why this is something we do so consistently as a community, which I will not be getting into here, one takeaway is that people definitely do get together with the best friends they’re in love with and sometimes it works out really well! Some of y’all are getting MARRIED. So there’s hope! Here’s what I’ve learned from those fine folks.

One of You Has to Make the First Move!

I know! I know you don’t want to. It’s very scary! The normal baseline fear of rejection is accompanied by fears of losing your best friend, hurting someone you care about, and the internalized fear of being predatory by being interested in someone who isn’t interested in you the same way. (Having feelings for someone doesn’t make you a predator, even if they don’t reciprocate them! Neither does expressing those feelings, as long as you listen to and respect the other person’s boundaries and reactions!) It’s possible that your friend doesn’t return your feelings, or not in a way she wants to act on, and making the first move means taking responsibility for what that might mean and how it might impact your friendship.

But someone has gotta, or you’re gonna spend the rest of your life hyper-aware of the fact that two centimeters of your outer thighs are touching as you sit next to each other rigidly on the sofa watching Masterchef Junior. Reader Heather reported success with this experience; saying “We were having a sleepover at my house, sharing a bed. We were laying there in the dark, talking about all kinds of things. I was saying how, even though I was attracted to more than one gender, I’d never dated or kissed a girl before. Then, we just looked at each other for a few seconds. Then, she kissed me.” If you’ve been harboring a secret wish that this scenario could feature you and your bestie, I regret to inform you that is in theory achievable.

In the anecdotal data provided by my respondents, it appears that the “impulsive kiss that changes everything, possibly while drunk” is a popular strategy, especially among the university set. In some respects it’s like, why mess with a classic, but this approach also leaves a lot of room for interpretation, including reactions like “pretending it didn’t happen the next day,” “playing it off as a mistake,” or “slipping into a months-long situationship that you’re pretending is just friends with benefits because neither of you want to admit you want it to be a real relationship.” Other options include having a verbal conversation about your feelings, possibly also while drunk — anecdotally, this seems to be maybe a better idea, even better if you’re having the conversation with some distance — over the phone, or messaging, so each of you has a little time to breathe and process without having the object of your affection staring you in the face.

It also makes sense to ready yourself for this to be difficult! It’s scary even if your bff does reciprocate your feelings, and both of you might be confused about how you feel. While some people described instant relief or joy, or “becoming official” almost immediately, more people described a transitional period that was a little tough to navigate. Reader Tréza says that while she’s set to marry her former best friend next year, the initial conversation when her friend confessed her feelings was rocky — she was “really confused and unsure how we could keep being us with this new density in the air.” It took months after that, a lot of talking and “a lot of fighting” before the two kissed; and even then “It took a long time for us to move from that kiss to dating… We didn’t want to fuck anything up I guess — our friendship, our other friendships. We wanted to be sure this was going to stick.” If your best friend DOES return your feelings, that’s fantastic — but maybe best to try to reserve any expectations for what exactly that might mean, at least in the immediate future.

Be Intentional About the Actual Dating

Assuming you and your bff do both decide you want to try something for real, you’re gonna roll your eyes, but you still have to communicate about it! It’s true you know each other better than anyone on earth, but you’re also in new territory, and it’s a dangerous time to make assumptions. Some people did find the transition into dating to be seamless — Emi, who was half of a couple who did move into a relationship immediately, says it was easy because “we already knew we liked each other as people and we got on very well and had stupid inside jokes and made each other laugh and knew most everything about each other.” That tracks! However, more often people reported that there were some rough parts about the shift from a friendship to a romantic relationship, and that talking about expectations going in would have helped.

If you and your best friend have both been pining for each other — and it sounds like you have! — you’ve probably both built up a fantasy of what your relationship could look like in your head. Without checking in about what those look like, though, you risk having wildly different expectations; you didn’t have the benefit of meeting on a dating app where both of you articulated clearly what you wanted, and while you might feel like you can read her mind, you’re wrong. Reader Heather said that while things felt easy initially, “it got harder when I started to realize we wanted different things out of the relationship. She didn’t want anything serious, whereas I was looking for something exclusive. I was so afraid to express what I really wanted because I didn’t want to lose my best friend.”

Even if you’re both on the same page about what a relationship looks like to you — and after years of talking about everything, maybe you are! — it’s also worth talking about what it means to both of you that you’re changing your best friendship. Readers spoke about surprising feelings related to a change in the relationship that were intense to navigate, even when it was a relationship they really wanted. Katie talked about how feelings of guilt about changing or damaging the “purity” of her friendship with her girlfriend impacted the relationship long after they got together — “I really thought that by entering a romantic relationship with my best friend, I was completely undoing that close friendship instead of building upon it and making it even stronger.” Similarly, reader Tréza realized she was feeling some layers of grief about “losing” her best friendship, even though she was happy to finally be together — “[She’s] still my best friend but she’s also my partner. That felt really overwhelming sometimes. Like, who would I talk to about [her]? Who would give me relationship advice?… It’s scary, to have so much wrapped up in one person. Can you really put on your best friend hat when your partner asks you to?” One thing she identified as being important was intentionally changing some dynamics from the friendship to the relationship, like how they approached arguing — “we worked really hard to differentiate and move on from how we used to fight as friends.” At the end of the day, while a good relationship might feel like a best friend you have sex with, that isn’t quite true! We have different expectations and dynamics with girlfriends than we do with best friends, and it really helps to be aware of what those are if you’re going to go from one to the other.

What If It Doesn’t Work Out?

Unfortunately, no matter how careful you are and how hard you work to make sure this crucial relationship is perfect, it doesn’t always last. Speaking, again, anecdotally, the people who got in touch with me fell into three categories as far as outcomes of their relationships:

1. We’re married or about to be
2. We broke up, but we stayed friends
3. We broke up and have never spoken again.

I think on some level many of us feel that if we ~went for it~ with our bff, it would either be the most perfect thing imaginable OR we’d ruin it forever. And while the people who got in touch were a very self-selecting group, in that they had an experience notable enough that they wanted to share it, it seems like in some respects that might be true. It might not work out, and in some cases it does seem like the emotional fallout is intense — “I felt not only like I was losing a relationship, but I also felt like I was losing my best friend,” said one person. Those who did return to a friendship afterwards often reported that that was difficult, too, with both parties often needing to take some space and time after the breakup. Many report that the friendship is different now, although not worse — “The friendship is different now, but that’s not a bad thing, that’s just from growing as people and life changing around us. I feel like if we hadn’t have dated, we always would have had that ‘what if’ hanging over our heads,” says Emi, whose relationship with her best friend ended after almost two years.

For queer people, friendships are often also family, sometimes the only family we have — it’s not a surprise they can end up becoming central to our lives and sometimes our most important partnerships, but it’s also unsurprising that the stakes feel (and are) very high for us in them. But also! Life is short, and love is (allegedly) not a lie. Morgan, who started dating her long-distance BFF after meeting her in person for the first time, says “The growth I had from her friendship is what has allowed me a good partner today. It is a journey I would do 100 times again if it meant our relationship would up the way it is now.” Itzel and Fátima, who started dating in Mexico City after Itzel became the first girl Fátima ever admitted feelings for, say “here we are 2.3 years later, being one of the happiest couples in the world (for real). Everything is so easy, we understand each other really well, our friends and many of our family members accept and respect us. And the most important thing… we are deeply in love.” Tréza, whose Scorpio/Cancer love story was truly gripping, says it maybe best: “She was standing there this whole time! All those heartbreaks and bad dates. She was right there and I was right here and we just couldn’t see it. But timing really fucking matters and I’m so, so happy we finally got it right.” Crossing my fingers for all of you weirdos!

Rachel is Autostraddle's Managing Editor and the editor who presides over news & politics coverage. Originally from Boston, MA, Rachel now lives in the Midwest. Topics dear to her heart include bisexuality, The X-Files and tacos. Her favorite Ciara video is probably "Ride," but if you're only going to watch one, she recommends "Like A Boy." You can follow her on twitter and instagram.

Rachel has written 1091 articles for us.

10 Comments

  1. I’ve been the one on the other side. It is awkward when one of your friends tells you they have feelings for you. I did not reciprocate the feelings. I tried to be sympathetic and compassionate but our friendship was never the same. I can’t really say why. I guess it just shifted the dynamics so much. I think I became hypervigilant about not taking advantage of her because of her feelings. Years later, we are still friends, but it’s different. All that being said, I admire her for being honest and courageous.

  2. I consistently fall for friends,so thank you for the hard truths. It used to go so badly, but I’ve learned a lot about the whole managing expectations and having conversations. Still no success stories, but at least have kept my dear friends.

  3. “Having feelings for someone doesn’t make you a predator, even if they don’t reciprocate them! Neither does expressing those feelings, as long as you listen to and respect the other person’s boundaries and reactions!”

    THANK YOU SO MUCH FOR THIS. SO VERY, VERY, VERY MUCH. Me and my best friend would have hot sex but then be an utter disaster, so devastating we would take down not only our friendship but possibly the world, but this does make me now feel okay to express feelings to the cute new friend I have with the pretty eyes.

  4. Some years ago my best friend drunkenly kissed me and we dated for three years and were really happy for most of it! (we didn’t stay friends afterwards though and even though it was a long time ago, it still makes me sad sometimes)

  5. Also, I have a close friend atm who I am heavily crushing on. We’re both sober and so drunken kisses are not an option!! which is such a pity because sober kisses feel like so much more of a Big DealTM

  6. You forgot an option: tell your crush / BFF. Discover she feels the same way. Discuss your mutual feelings and your feelings about possibly acting on them and all the things that could go wrong until said feelings die a sad, lonely death.

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