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# Thoughts from the Hobbit House: How Do You Break Up with a Friend?
- URL: https://www.stonewallnews.net/how-do-you-break-up-with-a-friend/
- Published: 2026-09-02T17:33:28.000Z
- Updated: 2026-09-02T18:54:16.000Z
- Author: Ryan Oelrich
- Tags: Columnists

### *Apparently, there’s no “Friendship Divorce Court”- and I have questions.*

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 After my recent article about how to make a new friend- spoiler alert: [invite them over to play Legos](https://www.stonewallnews.net/thoughts-from-the-hobbit-house-wanna-play-legos/)\- almost a dozen people asked me to write about the opposite:

**How do you break up with a friend?**

Frankly, I’m not sure I’m the best person to ask. In fact, I have made enough mistakes in this area to qualify for some sort of continuing education.

So I asked other people.

Twenty-seven generous individuals shared their thoughts, advice, heartbreak, and experiences with me via text, comment, over coffee, and while waiting in line to ride a waterslide. **Several shared some of the worst friend breakup horror stories that will probably forever haunt me. I’ll share those at the end of this article in the hopes no one ever repeats them.**

I’m grateful to every person who shared their wisdom, tears, and hopes for others.

This is also a tender subject for me because, like most people, I have been on both sides of a friendship breakup. I have been the person walking away, and I have been the person standing there wondering what the hell just happened.

The latter was one of the most painful- and ultimately helpful- experiences of my life.

### **My Friendship Divorce**

After college, I started dating a fellow and, as often happens in gay life, I eventually became part of his friend group.

He and I didn’t last.

The friendship group did… for a time.

Much to his probable frustration and stress, I remained firmly embedded in the group. We traveled together. We had sleep overs. We drank too much. We went to parties. We did pretty much everything together.

I’ve found gay friend groups can be particularly complicated because the guardrails between friendship and romance aren’t always there. It can be remarkably easy for friendship feelings to wander into romantic territory.

And wander they did.

One of my friends started dating my roommate and then my roommate became part of the group. Then they broke up. Then, in what can only be described as a spectacularly bad decision, I tried to secretly date my friend’s ex- the fellow who also happened to be my roommate.

**This did not go well.**

There were hurt feelings. There was drama. There was probably enough poor decision-making to qualify for its own limited television series.

I asked my friend if we could talk about what had happened. They said no. We never talked again. And, rather quickly, I was excommunicated from the friend group.

I had to start over.

It hurt.

But it was also one of the best things that could have happened to me although I certainly didn’t think so at the time.

Eventually, I realized that while these were all decent people, the group simply wasn’t a particularly good fit for me. Our interests, personalities, and lives had diverged. Losing that group made room for me to meet new people- friends I continue to love and appreciate to this day. So I am grateful that those friendships ended.

**I just wish I had handled the breakup better.**

### **Who Gets the Trivia Night?**

In hindsight, what I really wanted was a friendship divorce. I wanted someone to sit us down and explain the custody arrangement.

Who gets the favorite trivia night?

Who gets to keep the favorite café?

Who gets to attend Clare’s annual holiday party?

And what about the friends who are friends with *both* of you? Do they have to choose sides? Are there visitation schedules?

Apparently, there is no Friendship Divorce Court. There should be.

I remember showing up at my favorite trivia night and seeing my former friends there together- without me.

That hurt.

I hosted an annual Halloween party- complete with a ridiculous backyard haunted maze- and invited everyone and their mom. But I didn’t invite them. That probably hurt, too.

A mutual friend later told me she didn’t want to pick sides, but she felt like both of us were expecting her to. So she backed away from both of us. Honestly, I can’t blame her. Nobody wants to be Switzerland in someone else’s friendship war.

### **Why Do Friendships End?**

According to sociologist Gerald Mollenhorst’s research, friendships are surprisingly fluid, with many lasting only several years.

That means friendship endings are a normal part of life.

So why are we so bad at them?

There are plenty of reasons friendships end:

**1\. Natural drift**  
Sometimes nobody does anything wrong. People simply grow in different directions.

**2\. Unequal effort**  
One person is always calling, planning, checking in, apologizing, or trying to keep the friendship alive.

**3\. Value clashes**  
Sometimes you discover that you fundamentally disagree about things that matter deeply to you.

**4\. Unresolved conflict**  
Small hurts accumulate until the friendship becomes more painful than rewarding.

**5\. Different priorities**  
Jobs, partners, children, family, health, geography, or simply changing interests can pull people apart.

**And sometimes, unfortunately, the friendship just becomes unhealthy.**

### **So How Do You Do It?**

The 27 people I heard from had different opinions, but there were some common themes.

The most frequently offered advice was simple:

**Be direct when possible. Don’t ghost people.**

Sometimes friendships naturally fade. You stop initiating. They stop initiating. Eventually, you realize you haven’t spoken in six months and neither of you seems particularly bothered by it.

Another piece of advice I heard was almost the opposite:

**“Don’t break up with friends. Life’s too short. You may need to separate for a while, but keep the door open.”**

I think there is wisdom in that, too.

Here are some sample scripts for friendships that have run their course.

**“I've really valued our friendship, but I think we've grown in different directions.”** 
**“I care about you, but I don't have the capacity for this friendship right now.”** 
**“This relationship isn't working for me anymore, and I need to step away.”**

And here are a few even more courageous statements:

**“I don’t like who we are together anymore.”**

**“I don’t like who I am around you.”**

Not every difficult season requires a permanent ending. Sometimes you need distance rather than divorce. And sometimes you really do need to walk away.

### **There Is No Perfect Friendship Breakup**

Perhaps the biggest lesson I took from all these conversations is that there is no universal formula. Friendships are relationships, and relationships are messy. You can be honest and still hurt someone. You can be kind and still disappoint them. You can make the right decision for yourself and still grieve it.

And sometimes you can handle everything as thoughtfully as possible and the other person will still be angry and still get hurt.

That doesn't necessarily mean you did the wrong thing. What we *can* do is try to leave people with dignity. Don't weaponize their vulnerabilities. Don't recruit mutual friends into the conflict. Don't create a 47-slide PowerPoint presentation documenting every grievance dating back to 2014\. And, whenever possible, don't make someone discover that the friendship is over because they happened to see you having coffee with everyone else on Instagram. People deserve better than that.

**The Worst Friendship Breakup Stories Shared With Me**

Okay. Brace yourselves. I asked 27 people to share their experiences with friendship breakups, and while most offered thoughtful advice, a few stories made me stare at my computer and think, **“Well, at least I’m not the worst friend in the world.”**

Some of these stories are funny in retrospect.

Some are heartbreaking. I appreciate the courage of all who shared.

And some are so spectacularly awful that they deserve their own category.

Here are a few of the worst friendship breakups shared with me, shared with permission, but without names to protect all involved.

**The Group Trip**

One person told me about a friendship that had become increasingly tense. She eventually decided not to invite her friend on an annual group trip- a tradition they had shared for more than a decade.

The problem was that the friend didn’t know she had been uninvited.

Another person in the group apparently shared the trip details with her, and she showed up with her luggage, ready to board the van. Only to discover there wasn't room for her.

Because she hadn’t been invited.

She left in tears.

The person who told me the story said she expects to be haunted by that moment for the rest of her life. She deeply regrets how she handled it.

There are ways to end a friendship. **Surprising someone with a suitcase in hand at the departure point of a decade-long tradition is probably not one of them.**

**The Bar Night**

Another person told me he was at a gay bar with a group of friends he'd been close with for about five years. He noticed they were quieter than usual, but otherwise didn't think much of it.

Then one of his friends got up to sing karaoke.

Before starting the song, and in front of the entire bar, the friend announced that they no longer wanted to be friends with him because **he was too poor and didn’t dress like them.**

Then they sang karaoke.

I have so many questions.

What song did they choose?

Was it “Money, Money, Money”?

“Rich Girl”?

We may never know.

He walked out of the bar and never spoke to them again. As painful as the experience was, he told me that, in the long run, he was grateful to be rid of people who valued him according to his bank account and clothes. Which, frankly, is probably the healthiest thing anyone could have taken away from being publicly fired from a friendship during karaoke night.

**Extreme Ghosting**

And then there is the story that wins the award for **Most Aggressive Application of the Block Button.**

One person told me he had been best friends with someone for over two years. They talked every day. They had traveled together, lived together at one point, and even co-parented a puppy.

Yes.

A puppy.

They were planning a trip to Italy together when, at the last minute, his friend texted that they would just meet him at the airport. His friend's phone battery was almost dead, and apparently their seat had been changed, so they wouldn't be sitting together on the flight.

This seemed odd, but he boarded the plane.

He kept looking for his friend. The flight was large, after all. Maybe they were simply separated. He landed in Italy. His friend was nowhere to be found. No calls were answered. No texts were returned. He never saw his friend again. His friend changed their phone number and blocked him on social media. They never spoke again. The only thing he retained from the friendship was sole custody of their puppy.

To this day, he says he has no idea what changed, what he might have done, or why someone he had been so close to suddenly disappeared from his life without explanation.

And then, because apparently this story needed one more plot twist, he later met someone else who told him they had experienced essentially the same thing with this person.

I must admit, the puppy custody arrangement may be the most stable part of this entire story. But underneath the absurdity of it, there is something deeply painful about being left without an explanation.

We don't always get closure.

Sometimes we don't even get a goodbye.

And that may be one of the hardest things about friendship endings: **we can survive losing someone, but our brains desperately want to know why.**

### **Maybe Friendship Breakups Are Part of Growing Up**

I wish someone had told me earlier that not every friendship is supposed to last forever. Some people come into our lives for decades. Some for a few years. Some for a season. Some, apparently, for exactly long enough to teach us never to secretly date our friend's ex. All of them can matter. The ending doesn't erase what was good.

**The friendship ending doesn’t mean either of us is a bad person.**

Sometimes losing a friendship creates the space we need to find people who fit the person we are becoming.

I think about that old friend group occasionally. There are memories I treasure. There are things I would do differently. There are apologies I wish had been made- and conversations I wish we had been brave enough to have. But I am also grateful for what came next.

New friends.

New adventures.

New people who somehow tolerate me inviting them over to play Legos.

Maybe that's the strange thing about friendship.

We spend so much time learning how to make friends, but almost nobody teaches us how to let them go or say goodbye when we need to.

Maybe we should.

Because sometimes the healthiest thing we can do for ourselves- and for another person- is to acknowledge that the friendship has changed.

And then, as gracefully as we can, either let it go or change with it.

Preferably without fighting over custody of the trivia night or involving a puppy.

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