A Letter to My Ex-Best Friend This Pride

feature art: Autostraddle

It has taken me over five years to figure out how to word this, and I probably still won’t fully convey the years of feelings I’ve harbored about our friendship. As I sit here and imagine you potentially reading this, I simultaneously want to yell at you all the things I wish I would’ve said and also want to sit in your basement, listen to our Jonas Brothers mixtape, and tell you about how happy I am, how I’ve fallen in and out of love a handful of times, how I got one of my dream jobs (writing here!), how I’m really finding my purpose in the world. I want to hear how you’re doing. Not the Facebook post version but the whys behind your decisions. What are you motivated by now? Is motherhood what you thought it would be? Do you have any new passions? What keeps you up at night? However, telling you my life and hearing about yours feels inappropriate and out of reach.

When we last spoke, you had messaged me on Instagram. You told me you were reading White Fragility and wanted to know if you had done anything over the course of our 18 years of friendship that felt racist. I feel the sting of your message reverberate through my chest even as I write this. No amount of white-supremacy-deconstruction-church-book-clubs could ever bring you remotely close to understanding the hurt I’ve been wrestling with throughout our years of friendship. I’ve spent countless hours of therapy digging deeper into the work of unpacking the ways I perceive my own skin color and ethnicity, and the closer I get to the core, the more I see your face. How was I supposed to answer a simple Instagram DM with over ten years of microaggressions holding up the weight of “I’m sorry if I ever offended you?”

I told you I needed space and then never reached back out. Since then, you’ve bought a house, gotten a dog, sold that house, and had a baby. I saw the birth announcement on my mom’s pantry door when I went home for Christmas. I remember seeing your Subaru parked in your parents’ driveway, just three houses down from mine. That was the driveway where we drew with sidewalk chalk and drank Minute Maid, what we lovingly called “canned pee.” We stood on that driveway to watch your older sister go to her first prom. We rode our bikes up and down the driveway every summer day trying to seem like we weren’t spying on the hot young Amish guys building the house across the street. In the short drive between your driveway and mine, I always see shadows of the two of us running back and forth between our houses singing, laughing, riding scooters, eating popsicles. Between these two driveways we created worlds beyond our imaginations. We made lemonade stands. We exchanged presents on Christmas morning. We spent lazy summer nights dreaming of the day we’d find our soulmates and be each other’s maid of honor. We were going to have babies at the same time so we could sit together and eat off our large tummies. We planned our playdates with our children and talked about how our husbands would also become best friends. We even discussed what our lives would look like in retirement. Even though we would both have dementia, we would get matching scooters with little license plates that said “best friends” so, even if we forgot each other, we would somehow always have a way to know one another. All of this and more fills the space between my driveway and yours; it fills the space between your last message to me and my read receipt.

I’m sorry I never reached back out. I didn’t know how. I didn’t know what to say. I still don’t know what to say. As long as I remain who I am now — and you remain who you’ve become — I don’t see a future with the happy ending we always dreamed of. A few weeks ago, I had one of the best weekends of my life at a queer wellness retreat where I got to walk around naked, have a queer baptism, and go to a play party. I think you’re in Chicago now. You were probably helping your husband’s church over the weekend. You probably took the baby to see her in-laws. You might even have another child on the way. We’ve grown in two directions that aren’t quite opposite, but one is far more unforgiving than the other.

A broken heart with the words Best Friends inside it, surrounded by flowers.

Art by Viv Le

When I trace the map of our falling out to its origin, it’s clear to me now that our futures were never going to be aligned. It feels similar to having a codependent ex: The beginning was full of love, laughter, and infinite possibility. The end was long, drawn out, messy, irreparable. Even though I grew up Catholic, it wasn’t my family’s culture or reactions that eventually gave me trauma. It was your family’s evangelical, white-centric ignorance. Growing up, your parents took me in knowing I had a stifled relationship to my own parents. I went to church with you; I prayed before meals with you; I was even a part of your high school youth group. I almost got baptized in a nondenominational church because of you. I wanted to feel wanted and loved, and the only place I was receiving an outward expression of that message was with your family. Everything always seemed fine. Everyone always seemed to love each other. Everything was always possible through God. Everyone was always blessed. Every path was always sacred. Everything you ever wanted in a job, family, marriage, you got because you believed in a Jesus Christ who loves you but hates queer people.

I’m not blaming you for what you didn’t know then. I’m expressing my deep hurt for what you know now and still choose to believe. I will never forget the conversation we had in your mom’s piano room that Christmas. Before I told you to sit down, I was crying. You were already tearing up. We both knew it was coming. I had a girlfriend I was madly in love with, and I wanted so desperately for you to know and be happy for me, just like I was for you when you got married a few years prior despite my own personal bitterness towards heteronormative Christian marriage culture. Admittedly, I can’t quite remember how I told you I was some type of gay. I think I told you I had a girlfriend, and then you asked how long I’ve known. You cried and said something about how you don’t believe I’ll go to Heaven, but you can love me and pray for me. You asked if I could send you any books on Christians who are gay. I tried to comfort you through your tears, but my reach to you didn’t feel quite the same. I was so concerned with how you would take the news that I couldn’t process how angry I was feeling. I walked away from that antiquated off-white room knowing our friendship would never be the same.

For the next few years, this moment lived in a dark, locked corner of my heart. No one needed to know, especially my family, since they would’ve blamed me for ruining our friendship. Heck, you might still think that now. The first person I honestly shared this story with was the third friend in our trio. You know who I’m talking about. I think you two occasionally interact on social media still. You might’ve seen that the two of us are still good friends now. Once I came out to her, it brought us much closer. She told me she spent years angry with me for writing a pro-life piece about the benefits of chastity. Those were in the days I wanted to be a nun. I tried to explain how I’ve grown since then. Most importantly, I apologized and told her I know better. I know now that I hurt people with that article. I hurt myself with that article. She forgave me, and now I can say we’ve been friends for almost two decades. I wish I could say the same about us.

She had the courage to tell you all the things I couldn’t. She wrote you message after message with every Christian argument she could think of (even though she’s an atheist). “I still love you but” arguments were all she could get out of you. It was clear that even our strongheaded, lawyer-minded friend wasn’t going to get through to you, so how was I supposed to reach back out, knowing that’s how you felt? In retrospect, I feel ashamed I didn’t do the work of talking to you myself. I assumed that even if I did come to you with my feelings or all of the theological arguments in the world, you still wouldn’t really love me for who I am at my core, and that alone is what has kept me from reaching out all these years.

Whitney Houston’s “I Will Always Love You” is blasting through the speakers of the boba shop where I’m writing this letter. I always thought about this song as a ballad to an ex-lover, but it feels heartbreakingly appropriate in this moment. I will always love you, and I know you will always love me. Sometimes love isn’t enough. Most of the time, love has conditions. You didn’t step up and love me the way I needed you to, a way which will always conflict with your beliefs. Regardless, a day doesn’t go by where I don’t think of you. Years of therapy and personal boundary setting has showed me it’s okay for this to be what our relationship looks like now. It’s okay that 10-year-old me would be devastated to see we aren’t friends, because 27-year-old me is the happiest she has been in her whole life.

Even throughout our youth, we always joked about the funny, dramatic, sentimental speeches we would give at each other’s weddings. For some reason, that felt like a pinnacle moment in the future of our friendship. Even though I’m single and not getting married anytime soon, I think about how I will look at my wedding one day and see the space my ten-year-old-self wanted you in. This doesn’t make me sad, though. It makes me endlessly grateful. It will remind me that you helped me come out of my shy, sensitive shell. You showed me what it looks like to be goofy, smart, confident and maintain standards, especially with boys. Through our friendship, I learned more about myself than I could’ve learned from any other relationship in my life. You showed me what it means to be me and, because of that, I am so blessed and lucky to be the queer person I am today.

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Em Win

Originally from Toledo, Ohio, Em now lives in Los Angeles where she does many odd jobs in addition to writing. When she's not sending 7-minute voice messages to friends and family, she enjoys swimming, yoga, candle-making, tarot, drag, and talking about the Enneagram.

Em has written 71 articles for us.


  1. Love this. Friendship is just one of those things. I recently had a friendship breakup and I feels so good. I’ve also had friendship breakups that tore me apart, but I’ve come to peace with them. Like true peace.

  2. This is so beautifully written. I can almost see the two kids that you and she were then in front of me! Well done you for loving yourself, trying your best, repairing other friendships and knowing when to let some go.

  3. I feel like nothing quite hurts like friend breakup. And those scenes of your childhoods together hit me so hard! Oh my gosh, Em! Thank you so much for sharing this letter and your journey. I’m really glad you’re finding some peace, too.

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