Dating sucks.
Unwarranted advice from friends and family make things worse.
They mean well. But they often get the whole “empathy” thing wrong.
Years ago, a conversation with a friend shed light on how I was doing this to others…
Friend: I just got a divorce.
Me: I’m sorry man. That must really su—
Friend: Don’t be sorry. It was a terrible marriage and I’m actually much happier now.
That conversation illuminated my tendency to make assumptions.
Divorce = Bad. Breakups = Bad. Being Single = Bad.
I was just projecting my own values onto someone without taking the time to really listen.
A Flowchart for Talking to Your Single Friends
Unless asked for, your friend’s singleness is not your problem to solve.
Here’s a flowchart to help you have more productive relationship with single friends you want to help:

Using a empathetic approach helps us make less assumptions and be better listeners.
That means not pushing the hidden script that being single is bad, even if we don’t mean to.
Being single is not the problem
People treat singleness like it’s a disease.
Like it’s a problem to be fixed.
But we all know it’s much more nuanced than that. Some people love being single. Some people shouldn’t be in relationships now.
Singles also do a lot of rejecting. If the problem were to simply not be single, then any random partner will do.
Being single is not the problem. Finding the right match is.
So let me break out a chart of what’s truly helpful (or not) when it comes to your single friends:
Things that seem helpful, but aren’t | Things that are actually fuckin’ helpful |
I don’t get why someone like you is still single. You’re so great! | Listen without judgment or assumption. |
Why don’t you try (insert secret dating method)? | Don’t try to solve their problems. Your presence is enough. |
When you’re not looking, that special someone will come … | Invite single friends out to mingle with each other, set them up on dates |
How’s the dating life? Seeing anyone? | Have conversations beyond dating. You’re more than your relationship status. |
We all want the best for our friends, but sometimes mistake that for feeling responsible for solving their problems.
Aid without assuming. Support without solving.
The heart of empathy is simply being there.