“Don’t mistake being unfamiliar for being incompatible.”
​(two-minute read)

Reader,

A very quick ask - have you check out my TedX Talk on Friendship yet, let me know how it hit you!
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This week's newsletter is about why we need to give grace to potential friends.

Think about your best friend’s worst qualities.

They interrupt. They tell stories with no discernible destination. They’ve been “five minutes away” for the last twenty years.

You forgive all of it because you know who they are. You have years of evidence that they’re worth it.

Someone new pauses too long over dinner, and you’re ready to declare there’s no chemistry.

It’s hard to make new friends when we expect them to arrive with the comfort of old ones.

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🤝 THE FRIEND

When we started the DILFs of Larchmont, our dad crew, the admission requirements were pretty straightforward: have a kid, live nearby, want to get out of the house.

We did not administer a charisma test. Some of us would still be waiting for our results ;)

Bring together a bunch of dads who don’t know each other, and some conversations are going to be awkward. Someone’s quiet. Someone talks too much. Someone makes a joke that would have benefited from a second draft.
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On one meetup, I asked the same random dad where he went to college twice in the first five minutes of meeting him.

But the great thing about a crew is that people get to come back. The first conversation doesn’t have to carry the entire friendship.

You’ve probably seen this in your own life. A coworker you initially had nothing to say to becomes the person you spend half the day messaging. Another parent goes from a polite nod at pickup to someone who knows what’s happening in your marriage.

Somewhere along the way, you stopped having to think of things to talk about. You had enough shared history that the conversation took care of itself.

We understand this with our kids. We don’t expect them to walk into a new classroom and immediately feel at home. We give them time to find their people.

Then we walk into a dinner and expect instant chemistry by the appetizers.

🔧🔧 THE FIX

The mistake we make is treating ease as proof of potential. If the conversation flows, this could be a friend. If it takes work, we move on.

But some of what you love about being with your closest friends comes from familiarity. You know their humor, their history, and which questions will get them talking. You built that comfort together.

This week, give someone you liked a second hang, even if the first was a little awkward.

Change the setting if you need to. The quiet person at a crowded dinner might be great company on a walk. Doing something together gives you room to connect without the pressure of keeping a conversation alive across a table.

Look for kindness, curiosity, and some effort in return. You don’t have to force a friendship with everyone. But those qualities deserve more weight than whether someone nailed their opening appearance.

Someone could be in your life for twenty years. Give them more than twenty minutes to find their footing.

💡 THE RECO

Make a reverse bucket list.

I started doing this recently when I was down about a recent career misfire.

Write down five things you once hoped would happen that have already happened.

Maybe you became a parent. Found your person. Got paid to do something you love. Took the trip. Built a home where people want to gather.

For each one, finish this sentence: “There was a time when I really wanted…”

That wording matters. It makes you remember the wanting, before the thing became familiar and your attention moved to the next goal.

You can still be ambitious. Just take five minutes to notice how many wishes are now part of your ordinary Tuesday.

See you next week,
Matt Ritter

The Friendship Guy

“Friendship is the original life hack.”

🎧 Listen to The Buddy System on Audible​