The last time I heard from Trevor I didn’t respond right away. One day later a second message arrived reading, “Thanks for the reply.”

We’ve had a tumultuous relationship over the almost 20 years we’ve known each other, and I decided in that moment not to engage. Convinced he was trying to bait me, I didn’t want to argue over something as silly as a delayed response. I’d create a little space and the next time we crossed paths, it’d be fine. And I knew this, because that’s how it’s always been with us. Brilliant, funny, feeling people have flip-sides like everyone else, and I figured I’d just wait till he flipped back to the guy who I knew as reasonable and kind, and we’d move forward from there.

Last week, I found out he’d died. Within minutes, I was wondering if the decision I’d made was really maintaining a good boundary, or if I’d just been an asshole to someone in need.

It certainly isn’t the first time I’ve wondered that, and I’d put good money on it not being the last. Figuring out how to navigate challenging relationships is probably something I’ll be working on for the rest of my life.

I remember reading a blog from a longtime veterinarian a few months back, and he was talking about how hindsight is really a pain in the ass because all that clarity comes long after it’s most useful. All we can do, he suggested, was make the best decision possible, in the moment, with the information we have at hand. And when hindsight comes barging in later putting you on trial, ask yourself if you did the best you could with what you knew then, and save what you learn from hindsight for the next decision.

That’s all well and good, but right now it’s not clear how wishing I’d replied to Trevor is going to help moving forward; there are always going to be these moments in life where the smallest of exchanges have enormous impacts. Conducting myself in the most open-hearted way possible is key, but sometimes there’s wisdom in reticence.

How do we know when to step forward, and when to hang back?

When I was 10, my family moved to a small, agricultural town where my new friend’s family left their doors unlocked. Coming from apartment-living in rougher areas of San Jose, keeping a door unlocked seemed preposterous. I was taught to keep doors and windows locked, never pick-up hitchhikers, avoid strangers, never look at people in other cars — basically, keep myself to myself.

But had I cleaved to those insular ideas my entire life, I’d never have this family of friends who’ve saved me from fire and flood and depression and homelessness. I’d never have made fast friends with the funny, sensitive kid behind the counter at Abo’s, Trevor, who blasted Neil Diamond on the jukebox and made the rest of us laugh and think and feel. I know I’m not the only one wondering if the walls we erect between ourselves and others are too flimsy or too impenetrable, if they’re borne of fear or wisdom, or if having them at all is preposterous, but the question has to be asked again and again.

Read more Fritz: Stalk her:

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