I Accidentally Sent a GIF to My Dead Friend’s Sister

He would have found it hilarious. That’s the thing about losing someone who knew you that well.

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Retro 16-bit pixel art illustration of three small propeller planes flying across a bright blue sky in warm late-afternoon light. Two planes remain side by side in formation while a third pulls ahead and climbs toward the upper right, leaving a faint white trail behind. Bare winter trees line the bottom edge of the wide image, creating a quiet, nostalgic scene inspired by 1990s flight simulator video games.

Immediately after learning that Dan had died, I messaged his two sisters. Thank you for being such a good friend to him, one of them wrote back. He loved you very much. Dan had been one of my best friends since we were fourteen. Perhaps because I was in shock, my fingers slipped and I accidentally replied by sending his sister a ridiculous GIF.

I quickly deleted it, and we have not discussed it. I am devastated by Dan’s death, but right after the GIF mishap, what stung was that I desperately wanted to tell Dan about what happened. He would have found it hilarious. 

Dan’s sense of humor was brilliant, self-deprecating, and generous. He was the first friend I made in high school in Toronto, and it was his humor that drew me to him and kept us close. His yearbook quote was a wildly out-of-place reference to fighting a man with a purple hat. It still makes me laugh all these years later in its outright absurdity. 

That said, he did once lock me in a locker and leave me there. And on multiple occasions, he threw my school bag into the girl’s changeroom so that I couldn’t retrieve it. You’d be forgiven for thinking he was my high school bully and not my friend, but our bond never wavered through more than three decades. 

I am devastated by Dan’s death, but right after the GIF mishap, what stung was that I desperately wanted to tell Dan about what happened. He would have found it hilarious. 

For a time, Dan was a college instructor, teaching things like video game design and computer graphics. But his adult life was largely spent as an entrepreneur, He founded multiple companies and gave many young people their start. 

It was also spent chasing adventure. He loved racing dirt bikes; driving boats; and especially, flying planes as an amateur pilot, his lifelong dream. I was scared to go flying with him, but friends told me that in his first plane, the door would routinely swing open in-flight. It was the passenger’s job to hold it closed while Dan flew the plane. He said to me several times that he figured he’d die in a plane crash—but the freedom and sheer joy of flying was worth it to him.

He was wrong about that. On April 30, Dan was shot in the middle of the day in an idyllic Toronto park usually filled with kids and dogs; the very place where I am sitting now writing this. It seems to have been essentially random. There was briefly a small impromptu memorial at the site—a candle, some flowers, and a wooden toy plane—but when I went to visit less than a month after his death, it had all been thrown out.

Dan loved his wife and his family dearly, and he had a special place in his heart for his wide circle of friends. His funeral was the closest thing to a high school reunion that I have been to. Even those who hadn’t seen him in years said they would never forget the mark he left on them with his warmth, kindness, and humor. None of us could believe he was gone.

I was a pallbearer. As we buried Dan, three planes were flown overhead by pilot friends of his, one of them his own. On the second pass, it split off from the others and disappeared into the distance—the “missing man” aerial salute. But it wasn’t the planes that I’ll remember most. It was catching sight of the dirt at the bottom of his grave as we lowered him. When the casket was down, I touched it once to say goodbye. 

I’m sorry I accidentally sent that GIF to your sister, Dan. I know you would have found it funny that I did that. I’m just not sure she did.

I loved you, too, and the world will never be the same. 

But I’m still angry about that locker incident. Jackass. 

Gregory Levey has just finished writing his first novel. Dan helped edit it.

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