Okay, let’s talk about this best friend thing. Everyone thinks it’s all sunshine and rainbows, right? Having that one person who gets you completely. And yeah, mostly it is. But there’s a flip side, something I learned the hard way.

I had this friend, let’s call him Alex. We were inseparable for years. Went through high school, college applications, first heartbreaks, the whole deal. We practically shared a brain sometimes. You know the type. I figured we’d be those old guys sitting on a porch complaining about the world together.
The Downside Nobody Mentions
Here’s the thing, the con I experienced firsthand. When you’re that close, your lives get tangled up. Like, really tangled. We decided to start a small project together after college, just a side hustle thing. Seemed like a great idea. We knew each other so well, communication would be easy, right?
Wrong. Turns out, being best friends doesn’t automatically make you good business partners. We started having disagreements. Small things at first, about deadlines or how to spend the little money we made. But because we were best friends, neither of us wanted to be the ‘bad guy’. We avoided the tough conversations.
Instead of talking it out properly, we let things simmer. I’d get annoyed about something he did, but I wouldn’t say it directly. I’d just be a bit passive-aggressive. He did the same. That closeness, that fear of really upsetting the other person, it backfired. We weren’t honest in the way we needed to be for the project.
Eventually, the project fizzled out. But the damage was done. There was this awkwardness between us that hadn’t been there before. We tried to hang out like normal, grab a beer, watch a game. But that unresolved stuff was always sitting there.

- We stopped calling as much.
- Conversations got shorter.
- We started making excuses not to see each other.
It wasn’t a big dramatic fight. It was worse. It was a slow fade. And the reason it hurt so damn much, the real con here, is that losing a best friend feels different. It’s not like drifting from a casual buddy. You lose all that shared history, the inside jokes, the person who knew you when. The expectation of lifelong friendship makes the ending, even a quiet one, feel like a bigger failure.
So yeah, having a best friend is amazing. But the potential con? When things go wrong, whether it’s a slow drift or a big fallout, the hurt is amplified. The depth of the connection makes the potential pain that much deeper. It’s something you don’t really think about when everything’s going great, but I learned it. I really did.