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Meet the Guy Who AirDrops Pictures of His Dog to Red Line Passengers

James Guess is trying to spread a little joy on the Metro's most hated commuter line

Photograph courtesy James Guess.

There have been many proposals of how to improve the fire-ridden hell-ride that is the DC Metro, from installing WiFi in stations to reimbursing passengers who experience delays. James Guess has taken a more creative approach. Every time he sardines himself into a sweltering, overpacked train car, he AirDrops fellow passengers a picture of his dog, Henry.

Though Guess has performed this ritual every time he’s ridden DC’s least beloved transportation system in the last three weeks, the photo of a smiling Henry lackadaisically lounging in a car has reached relatively few people. Guess can send his photo only to people who have their AirDrop set on “public;” it usually ends up being around a dozen people a day. Of those chosen few, Guess says generally only one person actually opens the photo each day.

But what joy is brought to that one person! Henry is what doggo experts would describe as a “very good boy;” a rescue from the Humane Rescue Alliance that Guess and his girlfriend, Kelsey Weigel, adopted in February. Like any good dog parents, Guess and Weigel send each other pictures of Henry constantly to brighten each other’s days with some canine love. They’ve even helped Henry maintain his own Instagram. Guess says he figured other people would love getting Henry photos as much as he does.

Confession: I Airdrop this picture of my dog to everyone on the Red Line during my commute to and from work. from washingtondc

What compelled Guess to embark on this dissemination of joy? Perhaps it was a hearkening to his generous Midwestern roots: Guess moved to DC last September from the Chicago area. Or maybe, as the assistant audio video supervisor at the Shakespeare Theatre, Guess intended this pupper distribution to be a piece of living art, a commentary on our troubled times?

Not so. Guess, like the rest of us, was simply bored with his commute and was looking for a fun way to pass the time. “It’s harmless and it’s fun,” he says. “It’s a fun way to brighten up people’s mornings or afternoons when they’re coming home on the train.”

Unfortunately, not all AirDrop users are so wholesome. This spring, an innocent passenger just trying to slog through their morning commute was AirDropped an unsolicited dick pic by a total stranger in the car. Guess says he’s had intrusive instances like these—he was AirDropped a picture of a creepy clown in the past—but that he uses AirDrop only for a force of good.

Now that the dog’s out of the bag, those hoping to be surprised by some Henry pics will have the best luck on the oft-delayed Red Line. Guess commutes between the Van Ness/UDC and Gallery Place/Chinatown stops every weekday; you’re most likely to catch him (and his dog pics) during rush hour in the front two cars.

Guess has, so far, been able to remain anonymous. Though a Reddit post he recently made gained some attention, nobody has yet recognized him as the proud dad of the dog with the distinct facial coloring. That doesn’t mean others haven’t tried to uncover his identity: another recent Reddit post from a fellow commuter said when they received the picture of Henry, they tried to return the favor by airdropping a photo of a cat in a whimsically patterned hat.

In a twist of fate, though, the rider was unable to locate “James’ phone” to deliver the package of cuteness. Guess hasn’t had his AirDrop on public for around a year now, and doesn’t think he’ll turn it on in the future.

“It’s very much a one way street for me,” Guess says. “I don’t get to see anybody else’s pictures if they try to return the favor for fear I might get something…like a dick.”

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Jane Recker
Editorial Fellow