Ask Polly: My Best Friend Is In Love With My Sister!

Appearing here Wednesdays, Turning The Screw provides existential crisis counseling for the faint of heart. “Don’t make me come over there!”

Dear Polly,

Recently one of my best friends since childhood started dating my sister (whom I am also super close with). They seem pretty serious about each other and I want to be okay with it, but I’m having a really hard time with it. The main issue is I just have this primal response of UGHGHG NOOOOOOO which doesn’t feel totally logical when it happens, but here’s what I think it’s about:

1. I talk to both of them constantly, all the time, about everything. Particularly dating, as we are all ladies in our 20s and that is pretty much our main interest. You know how when your friend starts dating someone and then they don’t want to text with you, wine-drunk at 2 a.m., about “Real Housewives of Beverly Hills” anymore? That’s totally normal and healthy and you’re happy for them, but it’s kind of sad for you, and it’s really sad to think of two of the people I’m closest with in the world becoming a little less close to me because their primary person is /will now be each other. Kind of related, but in the worst part of myself, I’m sure I’m jealous they’ve found love.

2. I think it feels almost incesty to me. It doesn’t to them because when my friend and I were living at our parents’ houses and hanging out with each others’ families, I always went to her house. She really doesn’t know my family super-well. But she is someone who I would describe as being “like a sister to me” so it is so gross that she is dating my actual sister.

3. Normally we would talk constantly about sex and love and dating, and now… we just can’t.

Firstly, I have this super negative primal response, so I told them from the beginning I did not want to be involved, but phrased it more diplomatically as like, “It puts me in a weird position,” which is also very true. You know how annoying people are when they first start dating someone they really like and want to gush about them and how amazing they are and they don’t actually really know each other that well yet, so they fill in any blanks with more amazingness? Normally, I would call them out on their bullshit, both of them, because that’s our relationship, and now I KNOW when it’s bullshit because I know the person they’re talking about. But saying, “Actually my sister isn’t as dreamy as you think and here’s why!” is obviously not cool. So I’ve told them to leave me out of it. They’ve been okay but not great about respecting my wishes on that. At the same time it sucks that there’s this very important part of their lives that I’m left out of.

4. Finally, the way it went down was pretty shady. They live in different regions of the country and also a different region than I do, but had expressed interest in each other, both being cute single ladies interested in ladies. I said I didn’t like it, but my sister struck up a texting relationship with my friend regardless. My friend told me she’d stop if it bothered me. I said it bothered me, she said she stopped. A few weeks later I was about to leave the country for six months so I was having a going away party. My friend happened to be in town that weekend and was coming. My sister decided to fly into town under the pretense of attending my party for me, but it was very clear this was just a ruse to run into my friend in person, as I’d just seen my sister two weeks before. They hooked up that night, I obviously knew, and then they lied about it the next day, which surprised me, because I didn’t even call them out on it. I decided to ignore the whole thing and hope it would go away, I mean they live thousands of miles apart. But after I had been away for like a month, I got an email from my friend saying she hopes I have the heart to forgive her, she flew my sister out on a secret trip to visit her, and they really like each other. They didn’t want to tell me until they knew they were serious because they didn’t want to upset me if nothing was going to come of it anyway. Last year I had a super devastating situation where I was betrayed by a friend and as a result I know I’m hyper sensitive to that kind of thing, but I was really upset by how this all transpired. Particularly because I never forbid them from dating each other or anything, never flipped out, and when I was directly asked I said it bothered me and that’s it. There was no need for them to handle this like they did.

But what’s done is done and now they are together. There are a lot of potentially good things about this: I think they could make each other happy — at least I know I’ll like my sister-in-law! But it just bothers me so so so so so much. How do I just be okay with this?

In The Middle, But Left Behind


Most people who read your letter are likely to think: “They found love. Get over it. You should feel happy for them.”

But I get it. When I was in my twenties, my two closest friends in the world — my best friend and my exboyfriend — started sleeping together. I was fine with it at first, excited for them and surprised that my best friend (who took me out to lunch to tell me) thought it was going to be an issue for me. Then I found out that they’d kept it a secret from me for over a month, and everyone else I knew already knew about it. In fact, when we’d gone out together a few weeks before, they’d been making out whenever I left the room. So not only did I feel like a big asshole who was being openly fucked with by the two people she loved the most, but I also felt that they were each totally willing to sacrifice their friendship with me just to pump up the titillation of their affair. I was already in a pretty fragile place: My dad had died of a heart attack, out of the blue, a few months earlier. Now I felt like I had no one to turn to. No one could be trusted. The two friends I leaned on the most were careless with me.

When I tried to talk about it, my best friend wouldn’t hear it. I hadn’t been a good friend to her lately, so she wasn’t about to take shit from me about how she let me down. When the three of us spent time together, I felt self-conscious and neither of them acted like themselves, either. Soon after that, I moved away. When I went to visit, my exboyfriend would tell me that my ex-best friend was angry at him for having lunch with me, or he’d bail on me at the last minute “to avoid trouble.” If I talked to either of them on the phone, I was always worried that I’d say the wrong thing and it would set off a chain reaction. I was angry and upset, though, so I wasn’t very good at biting my tongue, and everything I said to one seemed to get back to the other.

At the time, I felt like I’d been standing still on the sidewalk when an eighteen-wheeler swerved and flattened me in an instant. Later, I wrote this cartoon about the unethical, self-serving behavior of urban hipsters. I retreated into my new boyfriend, but I struggled to make new friends because I didn’t trust anyone, I didn’t feel open or interested in anyone new, and no one I met seemed as smart or as interesting as my exboyfriend and my ex-best friend.

Now, I look back and think: Two people were in love, that’s all. They didn’t necessarily handle it perfectly, but neither did I. I had no claim on either of them and couldn’t really expect them to address the unexpected ways that their relationship made me feel betrayed and lonely and shut out. The three of us were extremely emotional, sensitive, confused people. At that age, none of us understood restraint or discretion. And I was full of unfocused anger and blame back then. I drank too much. I stepped on people’s toes and felt hurt when they got angry about it. I was a confessional, confrontational mess, and when you’re like that, people don’t exactly bend over backwards to address your complaints, no matter how terrible you might feel. All three of us just wanted to be heard and loved and supported, but not one of us was that good at hearing, loving and supporting someone else. Even if you take away the relationship between my ex and my ex-best-friend, I don’t know that the three of us could’ve stayed close to each other. We were too immature to tolerate how similar we were to each other.

Your situation is absolutely simple, on one level: Your sister and your best friend are now dating, and in love, and maybe they’ll spend the rest of their lives together. What can you do but grin and bear it? It’s great that they found love, that’s all.

But on a deeper level, you’re mourning the loss of these two intimate friendships, the likes of which may not be matched for years to come. Even if you stay very close with each of them (and you’ll hopefully be close to your sister no matter what), you may never feel quite as comfortable pouring out your heart to either one of them. You can’t recreate where you were before this happened, when you didn’t have to wonder what your friend would tell your sister about you, or guess what they might say to each other about this new guy you met, or this friend who’s getting on your nerves. When you’re young, so much of a female friendship forms around feeling totally comfortable admitting your biggest mistakes and deepest fears. How can you go there with two people who once felt like yours and now belong to each other? Even if you take pains not to frame this in the traditional, limiting perspective that sexual relationships trump all others, it’s still a big challenge. You trusted them completely. You told them everything. Now that’s going to change.

I hate to tell a really negative story about your experience. I just want you to know that I know exactly how terrible this feels for you. You call this thing between them “gross” and “incesty,” but what you’re mostly feeling is loss. You have lost something. When things settle down between them, or if/when they break up, your relationship with each of them may get better. But that’s not how it feels right now. Right now it feels like you’ve lost them both.

Maybe we all have to mourn the loss of this kind of unconditional connection at some point. My best friend and I used to talk for hours on end, without a pause. We used to write songs and perform together. We intuitively understood each other’s experience — not just our intellectual experience, but our emotional experience, our romantic experience of the people, places and things around us. Breaking up was like realizing that we’d never been that special, like it was all an illusion.

But fuck that. We were so full of ideas and so open-hearted and so young, and we really loved each other. How could you look back and sum that up as naïve?

So all I can say to you is this: Forget the “whys” of it. Forget how they told you about it, how you said you were bothered and they did it anyway. File all of that under: Two People In Love. You probably laid the groundwork for them to fall in love, too, because they had that shared love of you, that shared knowledge of you, right out of the gate. Maybe you learned, with each of them, how to be a good friend, how to listen, how to entertain, how to open up and tell the truth, and you taught them these things, too. But now they’re just two people in love, two people who want to be together. Just let them be together, and don’t slice and dice how it happened or what your role in it was or how you were betrayed or bullshitted or discounted or sidestepped along the way.

They didn’t fuck you over that badly, trust me. They told a few little lies to protect their chances at love, to prevent you from coming between them. That’s not ideal for you, but it’s totally understandable for them, and most people in their shoes would’ve done the same thing. Don’t make their “bad” decisions a sticking point for you, because all you’re doing is taking your pain (which is very tough to describe to an outsider), and trying to attribute a cause to it. They have not trespassed against you, OK? You’re going to have to drop it. You can feel angry, but you can’t blame them for that anger, because it’s really not their fault.

Furthermore, in reaction to this major loss, some part of you is going to want to draw up some rules, set limits, explain what you won’t stand for. I would be very careful about that. You can flag some obvious potential pitfalls of three-way communication, but I would not try to control what they talk about. They’re going to tell each other everything. That’s what people in love do. If they’re serious about each other, which it sounds like they are, they have to be honest. If you get pissed about information getting passed between them, you could hurt them and hurt yourself and make a big mess. Sadly, you’re the one who, by definition, needs to be careful and maintain control and not cause trouble. You’re the outsider, like it or not. Don’t lash out because you’re hurting. Don’t talk shit. Keep your nose clean. I mean it. This is your sister we’re talking about — she will be in your life forever, and you MUST be generous. If you have to detach a tiny bit, then do it. But don’t get sloppy. Don’t make a mess. Take the long view and be gracious, at all costs.

Most of all, though, I want to tell you to keep your heart open to them, as open as you can possibly stand. I know it hurts, but don’t close yourself up and walk away. After seventeen years of mostly being out of touch, I went to my ex-best-friend’s wedding last fall, and it was like dropping back into a life I lost a long time ago. Platonic friendships between women are defined in such casual terms. But they’re often much richer and more meaningful than romantic relationships. You don’t really see it that way when you’re young. I look back on exboyfriends and I still care about some of them, but it’s all relatively blasé. Close friendships with women age differently. The feelings don’t just dry up and blow away, because they’re not dependent on attraction or timing, they’re dependent on mutual honesty and vulnerability.

Even so, at that wedding, I looked at my ex-best-friend and thought: We may not spend much time together, before we die. Isn’t that stark? We’re in our forties and we live 2000 miles apart. We are a matching set, but we won’t ever go back to completing each other’s thoughts. How many people do you meet, who make you feel completely understood — sometimes to a fault? Not that many. There was a magic to our friendship, to our collaborations, to our most mundane conversations. It feels important to honor that magic, even though it also makes me feel a little heartbroken, to think of how I protected myself from the pain of it, and lost her in the process.

So keep your heart open. Admit that you feel terrible, and try to explain this loss without blaming them for having caused it. Let them off the hook, but don’t let them go. It’s not that easy to lean on someone. It’s a rare thing, to be able to do it without feeling self-conscious about it. You can and you should make new friends. But don’t give up on your best friend and your sister, and try not to see their love for each other as a betrayal of you. Don’t cut yourself off from two people you love. If you step back because it hurts too much, if you leave them behind, if a big wall comes between you and your sister, you’ll really regret it. For decades, you’ll regret it. Forgive them and keep them close. You will get caught in the middle sometimes. Life is messy. It’s no one’s fault. Forgive them, and don’t let them go.


Do you have a problem that could send Polly spiraling into an existential crisis of her own? Write to Polly and find out!

Heather Havrilesky (aka Polly Esther) is The Awl’s existential advice columnist. She’s also a regular contributor to The New York Times Magazine, and is the author of the memoir Disaster Preparedness (Riverhead 2011). She blogs here about scratchy pants, personality disorders, and aged cheeses.

Amazing photograph by Rachael Voorhees.