Friends Who Stay: The Five Things 30+ Years of Friendship Has Taught Me

I always say the same thing when people ask how Ben and I met, in front of Ben. Can I tell you my version?

He’ll just roll his eyes and let me go ahead.

We were in an art class in college, a drawing class, and this little ginger kid would not stop talking. The first time he sat next to me, he talked through the entire thing. I remember thinking, “who is this kid?” So the next class I came late on purpose and found a seat across the room. He picked up his chair, carried it across the room, and sat down right next to me again.

He kept doing that, every class after, and somewhere in there, I noticed I was laughing at things he said, and showing up early just so I’d be sitting where he’d find me. 

That was over 30 years ago.

Almost all friendships go quiet. The ones that stay come back.

We were close all through college. Then I got married, had Jake, and our friendship went quiet for a while. Not in a dramatic way, just in the way that happens when two people are in completely different seasons of their lives. He was still in his twenties. I was raising a kid.

We picked it back up when Jake was nine or ten. I was heading to the Twin Cities for something and asked if he had time to meet up. That was it. No conversation about where we’d been or why we’d drifted. We just started again. 

After that, I started making a point to go visit. I’d go for a weekend here, a weekend there. He used to host Friendsgiving every year, and I’m not exaggerating when I say he’d have anywhere from 20 to 40 people in his house. He’d make one big main dish, and everyone else would bring something to pass. I started showing up to those once in a while, and the friendship just kept growing back, like it had never stopped.

I think that’s the part people get wrong about friendship. They assume that if it goes quiet, it’s over. Sometimes quiet just means quiet. The ones that matter find their way back.

What “being there” actually looks like

Ben has been wanting to get his real estate license for years. He used to talk about it even back when I was still selling real estate myself. A while back, when he was going through a rough patch at work, I finally said to him — I think it’s time. You’ve talked about this forever. Do it.

He said, “How am I going to support myself, Kat, if I’m not selling a house? You don’t get paid until you sell something.”

So I told him exactly how it works. Get your license. Work under an established agent. Help with their open houses and showings while you build your own client list. Give it about three years before you go full time.

He’s doing it right now. He texted me a couple weeks ago — “I just took class one of eighteen.” I checked in on him later. “Where are you at?” “I’m ready to take my first preliminary test. Got all eighteen done.” He’s already talked to a realtor about helping with showings and open houses.

He told me he appreciated me supporting him on it. And here’s the truth about that — I didn’t have to fully understand his fear about money, or what it actually feels like to start over in a new career at this stage of life. I just had to believe him when he said he wanted it, and stand there while he figured it out.

That’s the whole thing, really. It doesn’t matter what we’re doing. You don’t have to understand it. You just have to be there.

And when I was planning the launch of Whispers Within Us in New York, I told Ben about it about a month ahead of time. It was a weekday. I told him directly — you don’t have to come. I just wanted you to know it was happening. He knew I would love if he could be there, but of course, I understood if it wouldn’t work. 

I didn’t hear anything else about it. Then, just a few days before, he texted me asking about hotels.

I didn’t even understand the question at first. “Wait — are you coming to New York?”

“Yeah.”

I genuinely didn’t believe him until we were packing to leave.

He flew in. Was there for about 36 hours total. Flew home the next day.

I think about that a lot. Him showing up meant so much to me, it was a Tuesday, it cost him money and a day of work, and he’d be back on a plane before he’d even adjusted to the time zone. He came anyway, because it mattered to me, and that was reason enough for him.

Thirty years of small, ridiculous history

People who’ve known each other a long time accumulate a pile of stories that don’t mean anything to anyone outside the friendship and mean everything inside it. Ben and I have a lot of those.

There was the time he called me out of nowhere and said, “What are you doing for the next three days?” Turns out he was taking a 26-hour Greyhound bus to buy his dream car and needed someone to help drive it back. We took the scariest Greyhound either of us has ever been on — at one point the driver left the interstate, pulled into a vacant gas station in a residential neighborhood, got out, locked the doors behind him, and came back ten minutes later. Nobody on that bus knew what had just happened. We never asked. Honestly, we didn’t want to know.

But we got there, and he bought the car. We took turns driving it back to Minnesota. We laughed so much and had just the best time together on that trip. 

There was also the time he moved to Arizona and needed his Volkswagen driven down — another 26 hours, this time so he could fly back and get his other car. And somewhere in college, after a night of drinking, we both ended up at a tattoo shop with a hilarious story and two tattoos we would never forget. 

None of this is the point of the story, exactly. It’s just what 30 years actually looks like up close — not a single defining moment, but a long pile of moments nobody else would care about, that somehow add up to everything.

The five things 30 years with a friend actually teaches you

If you’d asked me in my twenties what makes a friendship last, I probably would have said something about chemistry, interests, shared history, or just luck. Twenty years in, I’d say something different.

#1 Real friends show up

Real friends show up no matter what’s going on. Always — good times, bad times, whenever, because they’re there for you, not for the version of your life that’s easy to be around. That’s different from what I call fair-weather friends, the ones who show up for the celebrations, the engagement parties and the promotions, but go quiet the moment things get hard. Devastation, big life changes, the messy middle of a divorce — that’s when you find out who was actually there for you, and who was just there for the party.

#2 It’s okay for friends to go quiet for a while

I’ve also learned that it’s okay not to talk for a while. The friendships that last aren’t always the ones where you check in every week. Friends who really love you are okay to go months without a word and are ready to pick the conversation up exactly where you left it, like no time passed at all. There’s something genuinely rejuvenating about that — finding out the connection didn’t need constant maintenance to survive.

#3 Some seasons you will give more. Others you will receive more. 

The truth about long lasting friendships is you have to be okay with the friendship being uneven sometimes. There are seasons where you give more, and seasons where you receive more, and you can’t keep score waiting for it to balance out. You have to be generous enough to walk what feels like a one-way street for a while when your friend is the one going through something. And you have to be humble enough to actually accept the help when it’s your turn to be the one struggling and they’re the one offering.

#4 You can’t make someone match your effort

I’ve also come to realize and believe you can’t make someone match your effort. You can only decide what you do with that information once you’ve noticed it. That’s not the same as giving up on someone — it’s just refusing to spend years over-functioning to compensate for a friendship that isn’t actually mutual, and not taking it personally when someone is simply somewhere else in their life than you are.

#5 The kinds of friendships with a few real fights are the ones I trust the most

This is one I think may be the biggest one: The friendships that last aren’t the ones with the least conflict. They’re the ones where you’ve actually had the hard conversation and survived it. In that much time, there are bound to be some disagreements; what actually keeps a friendship alive is being open and honest about your feelings, and not bottling them up to “keep the peace”. Twenty years with no friction would worry me more than twenty years with a few real fights in the middle of it.

What it looks like from the outside

I think about the people who get this right, and the people who don’t, and the difference usually isn’t dramatic. It’s not one big betrayal or one big gesture. It’s just whether someone shows up the tenth time the way they did the first time.

If you’re sitting with this and thinking about your own friendships, you probably already know which ones are which. You don’t need a checklist for it. You knew before you read this blog whose name you’d want to see show up on your phone on a hard day, and whose name would make you sigh a little before you picked up.

That knowing — the quiet, fast certainty that doesn’t ask you to think it through — is the same thing I write about in Whispers Within Us. Most people assume intuition only shows up for the big decisions. A job. A move. A marriage. But it’s there in the small rooms too. It’s the thing that told you, the very first time you met someone who turned out to be a fair-weather friend, that something was a little off, even when you couldn’t explain it. It’s the thing that told you, the first time Ben sat his chair down next to mine, that I should let him.

Learning to trust that voice doesn’t just change the big moments in your life. It changes who you let stay close to you in the small ones too.

At the beginning of this blog, in that photo from under the billboard in Times Square, Ben’s standing right next to me in it, the way he’s been standing next to me since 30 years ago in our drawing class.

And thirty years from now, I hope you have a photo like that too — with whoever it is in your life that just keeps showing up. 🫶

📖 If you want to learn to trust the quiet certainty that’s already telling you who those people are, Whispers Within Us is available now.