If this quest piques your interest, you can follow it more closely on Patreon!

The reason for messaging Sarah and Colin was to make sure they were OK with me doing this whole project, since it had so much to do with Sam. Without the family’s blessing, this trip would not occur. Bob and Ann had given me this, and now it rested in Sarah — Sam’s sister’s — hands. I messaged Sarah. The phone call would be with her husband Colin.

I did stun them a bit, which I understand. The idea of focusing on a painful story — the story of your brother and fiancé’s tragic death — is not an easy idea to process. How could it be? When Colin called, he filled me in on their immediate reaction. He wanted to know more about the book. What was the point?

I filled him in on the idea and how it had developed. I talked to him about my questions about friendship, and how so many of them trace back to Sam’s death. I shared the data on friendship decline, and how a story like this might speak to the deeper questions lurking under the surface of people who might be drawn by a story about a road trip to Wrigley Field. I said something about it being different for them — for family. Colin stopped me.

There’s a lot I don’t remember about the days after Sam’s death. I remember a few things about a funeral — and those vividly — but the rest is a blur. Colin mentioned his comments to me. I had forgotten them entirely.

Colin’s speech went into the development of his relationship with Sam, the “kid brother” of his girlfriend, now wife, Sarah. At first, he was the pesky young kid — lovable, but not someone Colin factored into his life nearly as much as the woman he loved. This was a little dude who came as part of the deal.

What surprised Colin was that the relationship developed into something far deeper than he expected. At the funeral, he reflected and named their relationship: best friends. His grief was for more than a “kid brother,” as devastating as that would be. His grief was the loss of the friendship he’d married into — and come to depend upon. So Colin informed me that he understood my quest more than I realized. That’s why Colin will be joining us.

As Colin explained this to me, it dawned on me that I was currently experiencing something similar.

In my case, as an only child, I’d always wished for an older brother or sister. It always seemed like a wonderful thought to have someone near my age, but just a bit ahead of me. The older sister, in my mind, would have explained girls to me. They were always so baffling, and the ones I found myself talking to were the ones I kind of liked and couldn’t quite comprehend. A sister could have schooled me on their mysterious ways.

A brother, though… we could have played baseball together, instead of me waiting for Dad to get off work so I could have a very ill-equipped partner to play catch and practice with. We could have ridden bikes together, and played one-on-one on the old metal basketball hoop on the dirt driveway.

When I met Michaela, her older siblings felt like obstacles. They were people who I had to impress and convince of my capability to care for their sister. I especially felt this way about Nat — that is, Dr. Nathaniel. Michaela viewed him as being very well-on-his-way in life, as a medical resident, husband, and father. To me, this was very intimidating. I was recently divorced, not finished with my degree, and back in a rental house. My main objective was to project that I was on track and capable of successfully taking care of his sister.

As the years have gone by, Nat and I have slowly become more acquainted. Home projects, similarly aged kids, bikes, and baseball emerged as similarities. It didn’t hurt when I chose to be a Cubs fan — even though Nat, being from St. Louis, is a fan of the rival dead birds — or, excuse me, Cardinals. Now we had an easy entry point into conversation, whether during the season or in between as we tracked the teams’ off-seasons. It wasn’t long before catching a game together entered the discussion.

The first trip came up because I had work-related reasons to pass through St. Louis during one of the Cubs/Cardinals series. I had never been to their ballpark and wanted to check it off my list. When I mentioned my intentions to Nat, he was immediately intrigued. I had a friend to crash with at a local seminary and had to leave the next morning, so it was a pretty low-cost and low-risk endeavor. If we drove each other nuts, it would only be for an afternoon. Nat booked a ticket on my flight out and one back later the next day, and a trio of tickets were purchased for the two of us and my buddy Caleb.

You learn a lot by traveling with a person — even more when you face a challenge together. In this first case, we had the opportunity to learn a lot!

The chances of rain entered the forecast as we prepared for the trip, but it seemed that the storm might roll in after the game. We remained cautiously optimistic. Our flight was smooth, Caleb picked us up, and he and his wife welcomed us to their new apartment. We figured out the train to the game, and off we went.

The clouds rolling in did look a little ominous, but the lightning sealed the deal. As we approached the ballpark, the official word came down: rain delay. OK, no problem. We had all night. We found a great-looking burger place and walked through the light rain to get there.

Our first challenge was due to our personal appearance — we weren’t quite prepared for the level of class expected at this “burger joint.” We came in very underdressed and wet, but no service was refused. The bill was steep, but the food was delicious.

We walked out to a cloudy but dry city streetscape. We had a ways to go to the ballpark, so we decided to download an app and ride electric scooters. As we started down the street, the floodgates of the heavens flew open and it began to absolutely pour. Within 30 seconds we were entirely saturated and could get no wetter at any place on our bodies. We were effectively submerged.

At this point, as we yelled to one another in panic and for the sake of choosing our course, we decided to bail and get to the train, a mere five minutes away.

I do not recommend riding an electric scooter through 2–4 inches of standing water on urban streets. It is terrifying. What is under my wheels? Will this little front wheel disappear into a pothole and buck me off and onto the pavement? — legitimate concerns!

It turns out that the scooters also stop working — and suddenly. As we passed through an underpass, they died one by one, and we were faced with walking the rest of the way. At some point though, there’s no getting wetter. We calmly sloshed the rest of the way, and it began to become hilarious.

We arrived at the train station as the most drenched passengers. Those with umbrellas or wet hair looked on as the water drained out of the bottom of our pant legs. Caleb snuck off behind a pillar to wring out his pants, and we stood guard to protect his dignity. The train arrived as we plopped down on the benches, oozing water like three soaked sponges.

As we re-created the story of our journey to the station, began to brainstorm about making the rescheduled game the next day, and fell into fits of laughter like teenage boys, we heard an announcement over the intercom: the tunnels had flooded, and we were being asked to exit the train.

We exited out and back into the rain in a slightly sketchy part of town. It was way too late, and all we could do was laugh.

We made it back to Caleb’s apartment eventually — to the relief of his wife — surprisingly energized. We did make it to the rescheduled game the next day. The Cubs lost to the Cardinals on a putout at home plate in the top of the 9th. I had to jump in an Uber to the airport. Nat and Caleb stuck around for the regularly scheduled second game together. Nat and I have recounted our adventure to as many as will listen. It ranks as one of the highlights of the last decade of my life.

This past week, Nat and I went on what is now our 4th annual brother-in-law trip — this time to Boston, where we met his brother-in-law Troy for a day in the city and a ballgame. We ate great food, toured Fenway Park and the Freedom Trail, and caught an entertaining game in the evening. It rained that day, but almost exclusively when we were inside. We even got a double rainbow in the sky over Fenway in the early innings!

On our second and third summer trips — to London (for Cubs vs. Cardinals!) and Wrigley Field — Nat and I discovered that we both like art museums as well. A formula is falling into place. We visit a city, a ballpark (ideally to see the Cubs, Cardinals, or a team we both want to lose like the Dodgers), some great local food, and an art museum. We’re already scheming about next year.

It turns out that the guy I once saw as an obstacle — the older brother of my sweetheart — has become one of my best friends. I get it, Colin, and I am so sorry for all that you’ve lost. I can’t wait to see you in about a month. Let’s see what memories lie in store for us.