Brutal, Cruel and Awkward Stories of People Breaking Up with Their Best Friends
Illustrations by Mai Ly Degnan


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Brutal, Cruel and Awkward Stories of People Breaking Up with Their Best Friends

The reasons range from paedophilia and white privilege to Evangelicalism and pathological lying. Here we go.

This article originally appeared on VICE US

Breakups suck, and they're not something only people in sexual relationships experience. Remember that one season of Entourage where E went rogue and tried managing clients other than his BFF Vinny Chase? That type of stuff happens to everyone at some point, though the average friendship rift typically doesn't involve famous people (or fragrant use of the word "bro"), even if the fall-out is equally melodramatic or mundane.


Shit happens, people get older, and friendship bracelets eventually tear. Even if the specs are petty, the way we feel after these platonic breakups go down is legitimately painful and can haunt us for years. Sometimes we learn stuff from the experiences and move on, other times we don't. Below are a series of anecdotes that detail the messy entrails left after particularly brutal best friend breakups.

She Fucked Our Friend's Dad

I had a best friend from age four to 15, and we stopped being friends because I found out that she had been fucking our friend's dad for about two years. He was over 50 and they started fucking when she was 12 or 13. And the guy was gross! He worked in a pen factory and smoked about 40 cigarettes a day—plus he had rotting teeth, dressed like it was 1982, and I'm pretty sure he had a mullet. He was a creep. My best friend would sneak off to meet this guy all the time, but she told me she'd met someone on the internet and would brag about how much butt sex they would have in the back of his car.

The way I found out that the real guy she was fucking was our friend's dad and not some random AOL chat dude was that she told our friend who happened to be dating the guy's son. All very Jerry Springer. At the time, I was working at a shitty hotel. I left work and the dad-pedo was waiting outside for me and asked to give me a lift home. He then proceeded to tell me that they weren't having sex—they were just friends. Obviously, that was a crock of shit.


Next thing I knew, the guy's wife found out and threatened to kill him. Most of the town found out and I think he lost his job. His wife eventually divorced him. Everyone sort of turned on me because, as her best friend, they all thought I knew. It was pretty horrible.

Our relationship officially ended with her writing me a note saying that she didn't want to be friends anymore. I was devastated. She was like my sister. When I received her note, I went to her house and ripped the letter up in front of her and called her a slag! She said nothing. After that, I saw her a few times in the street, but she wouldn't even look at me. In retrospect, I should have called the police on that creep she was seeing. Fucking pedo. — L

White Privilege and the Tony's

The friendship ended the night of the Tony Awards a few years ago when Audra McDonald received her record-breaking sixth award. We'd known each other for a few years and were very close. He had a boyfriend who was super nice, and just the three of us watched the show. They demanded silence during the actual show, but we could talk during the commercials. They were theater gays.

The one I was closer with was an optimist about everything—each performance was "amazing," there were lots of fake-ass tears of joy, etc. I would make comments throughout the awards shows that were less "omg what beauty" and more "all these people are white."

After Audra had her big win, we got into an argument. My friend and his boyfriend said I was too critical, especially about calling out racial differences during the award show. They were mad that I had made comments about the racial stereotypes in the event's musical performances, the lack of people of color overall, and how even though McDonald was winning such a big award, it didn't lessen the fact that there was still a giant lack of people of color and all these fucked-up stereotypes. They just wanted to sit there and escape in a world of theater. I think they've had tough lives being gay, so me being there and talking shit about racialized performances during their escape time didn't go over so well.


What really killed me was when the boyfriend said to me, "You speak about race like my parents." They are from the south and were so uncomfortable talking about racism that when I was speaking against it, they actually compared me to their fucking racist parents. They wanted to be racially unaware or "post-racial." Two fucking white homonormative theater gays were calling me racist for calling out shit about the Tonys. I was so mad I started going off. We'd had a whole punch bowl of drink. It wasn't cute. We argued about my comments, but then it got much bigger.

I ran out of their apartment about 20 minutes later, but forgot my bag, so I had to go back inside. The whole thing was so awkward. I grabbed my bag, and I remember standing outside their door. I was like, 'So see you soon?' And they replied, 'Sure…' We've never spoken since. — S

The Friend Who Lived a Double Life

I had this really eccentric friend who was one of the most personable, smartest people I have ever met. We became close when we were studying abroad in Paris. I thought I knew him super well and even went to this dude's house for Christmas one year.

Slowly and slowly, it became clear that he lived multiple lives. We had a core group of friends, and apparently he'd act differently around each of us. For example, he had a girlfriend and he didn't tell our friend group about her, and he didn't tell her about us.

Based on what my other friends or acquaintances said about him, it often sounded like they'd be describing a different person from the one I knew. He'd be an intellectual around one person, but a bro around others. He'd play into people's desires to project the type of identity he thought they were looking for. The only way to describe it would be to compare him to a con artist, though he conned us without necessarily taking anything. I'm not sure how he benefitted from creating these various personas he'd embody around different people.


When we got back from studying abroad, he sent an email breaking up with our friend group, myself included, basically saying that everything we knew about him and our three-year friendship was a lie and that he never wanted us to contact him again. Here's an excerpt from an email he sent our five-person crew. The subject line was "Please don't respond."

There is something you all need to know. When we were together in Paris, you got to know a fake version of me. It's not like there was something underneath it all, though. Really, I have just lived most of my life as a liar. I stopped talking to you because I wanted to distance myself from that. Nobody should live like this. It's not right. Read the email, be disgusted by its verbosity, and forget me. You never knew me anyway.

I never really saw him again, but I did some research and found out he lives with his foreign girlfriend in the Midwest. I know this because he got arrested protesting with the Black Lives Matter movement last year and I saw his mug shot. — K

The Atheist vs. the Evangelical Christian

In college I became best friends really quickly with my roommate, but she was an Evangelical Christian and I was an atheist. We tried to find similarities anyway and were inseparable for a while. One day, I was really depressed and she came home and hugged me. I started crying and she said she'd pray for me. I couldn't handle it and I blew up at her, saying she was too smart to believe "this shit" (my exact words).

She turned me into our dorm's RA the next week for a bottle of wine I had at our place. I didn't see her again until her wedding, and even then it was beyond repair. We both cried a lot when we saw each other, but the damage was done. — R


The Roommate from Hell

He was my best friend and we lived together in a dorm. When he decided we were not friends anymore, he made my life a living hell because he couldn't move out. He forbid me from putting my shampoos and stuff in his shower rack, and he moved all of his kitchen things into his own section so we had to have two sets. I started storing my shampoos on the floor of the bathroom to agitate him.

Then he started doing stuff like putting ear plugs in at night and setting his alarm for like 03:30, then letting it ring until I had to get up and shut it off. He also went into my storage bin and threw out all of my condoms. He deleted me and all of my family members from his phone and on Facebook. He'd post Tumblr quotes about me like a melodramatic bitch.

And since he could not communicate with me, he would just blast songs to tell me how he felt, often Mumford & Sons or Avett Brothers. Brutal. He made our living arrangement (which was a studio—no bedroom separation) as excruciating as possible to ensure the point was clear: our friendship was over. — B

I didn't see her again until her wedding, and even then it was beyond repair.

The Disappearing Act

It started with the classic friend-zoning moves: She stopped liking everything I posted on Facebook. She took weeks to respond to my calls. Birthday cards turned into birthday texts. Then there was that business trip to my city where she "could probably make time for coffee." But I knew something was up when she had to crash on my couch for a few days because the "hotels were too expensive" and left me $20 in a thank you card from CVS. Either she thought that four-days on my couch really should only cost €18 (fair), or it was some kind of very bad tip. To this day I don't know.

Our break up after that was an unspoken one. She disappeared without explanation, only to re-appear again half-a-year later on my Facebook feed, clad in a white-lace dress, bouquet in hand, brand new husband at her side, and with whatever-her-fucking-name-was from her soccer team as her bridesmaid. — M


The Homewrecker

When I was 20, I experienced my first serious breakup with my first serious girlfriend. I was kind of a mess, and got really tight with a dude I met in a college class around the time. He had also just had his first big-boy relationship fall apart, and we bonded over broken hearts, marijuana, a desire to write professionally, and probably some simmering homoerotic tension (just kidding).

He told me everything about his breakup, and I told him everything about my ex. I ended up bringing him for homie support when I went to hang with her for the first time after we ended things. When we left, I remember him describing her as "enchanting" and that he now understood why I was so hung up on the relationship.

Flash-forward a bit, and he and I got into our first fight since becoming best mates. I was writing my first professional freelance article and he offered some sound advice when I bounced an idea off him. I told him I liked his tip, but he then asked if he could split the by-line with me. When I said no, he laughed and said in front of a group of friends, "It's not like VICE would ever hire you anyway."

I decided to get some space by essentially ghosting on him, and we drifted. A few months later, I found out he was dating my ex—the one I told him everything about and introduced him to—through Facebook. What happened between us after that is pretty sophomoric, but our friendship was kaput. From what I'm told, he's currently living with my first love in Spain. I'm not quit sure—I haven't spoken to either in 976 days, but who's counting? And here I am, typing this article by myself in VICE's new, empty office. I'm still not sure who came out on top. — Q

All names have been changed to maintain anonymity.

Follow Zach on Twitter. Check out Mai Ly Degnan's illustrations on her site.