Joshua Taylor Cavallero didn’t notice the other bicyclist at first. Cavallero, who is better known by his Instagram handle, BikingDC, was focused on setting up the camera he wears on his helmet as he walks into restaurants, picks up orders and delivers them for Uber Eats to hungry residents and workers in Washington.

It wasn’t until Cavallero entered Spice 6 that he realised the scene he had just walked past: another food delivery worker, with a broken foot, holding onto a walker as he locked up his bike.

Cavallero, who posts videos of his deliveries on social media, captured the moment as the other man walked into the same restaurant as him to pick up a food order.

“You’re riding a bike with a broken foot?” Cavallero asks.

“Yeah.”

“And you’re carrying this around, too?” he says, referring to the walker.

“Yeah.”

“On that bike?”

“Yeah.”

“Bro, what are you doing? Are you serious?”

“I got bills to pay, bruh.”

Cavallero tells him he respects that. He then offers to send him a tip through Cash App. The man tells him he appreciates it.

“Nah, I appreciate you, bro,” Cavallero says. “You’re out here grinding, man. You’re really getting it done.”

What happened next marked a pivotal moment for that man, whose name is Kevin Ross, and for Cavallero.

If you follow BikingDC on Instagram or YouTube, then you’re familiar with the appeal of Cavallero’s videos. They offer a window into the food-delivery business and the lives of residents and workers in the city. In the videos, he zips through streets on his bike, sometimes while balancing drinks in his hands. He also talks to restaurant employees, security guards and customers.

Those encounters are brief and usually upbeat. Even after he got hit by a car, Cavallero’s exchange with the driver was friendly. A video from that day also ends with an unexpected act of kindness: the customer whose drinks were spilt in the crash, and then replaced by Cavallero, hands him a bag filled with first-aid supplies.

“Seeing him care as much as he did and make me a first-aid kit, it meant a lot to me,” Cavallero told me recently. “It really did.”

In the past few years, Cavallero’s Instagram page has accumulated more than one million followers and his videos have received millions of views. I asked him why he believes people have been drawn to those snapshots of the city. He said most of the time people are in their own world and focused on their own things, and in those videos, he tries to make connections with individuals, whether they are initially receptive or not.

“If I see a grumpy security guard, I’ll still talk to him. I’ll try to find something to make him smile or laugh, so when I roll away, I know it’s all good and he’ll have a better day,” Cavallero said. “Everybody’s always saying, ‘DC people are like this’ or ‘DC people are like that’, but it really starts with you and how you are talking to these people.”

In that sense, the video of Cavallero meeting Ross is no different. It shows a quick, friendly exchange. But shortly after Cavallero posted it, it went viral. It has drawn more than five million views on Instagram and YouTube. In the comments, people have expressed respect for Ross and spouted anger at a country that forces people to work through injuries to make ends meet. They have also talked about wanting to help Ross.

I spoke to Ross recently. The 44-year-old said that on the December day he met Cavallero, he was worried about how he was going to pay his rent that month and other bills that were due. As he tells it, he was hit by a car in September and spent two weeks in the hospital. After returning home, he tried at one point to donate plasma to bring in some money but was turned away because of his injury. When he started delivering again for Grubhub, he wasn’t supposed to put any weight on his foot, so he decided to use a walker when he wasn’t pedalling.

The day after Ross met Cavallero, he planned to ask a neighbour for a loan. Then he looked at his Cash App. About $2,400 had been added to his account. In the days that followed, more money started appearing.

Ross said he didn’t know at first where that money had come from. He didn’t know that Cavallero had posted his Cash App information along with the video of them meeting. When Ross finally saw Cavallero’s post, he read through hundreds of comments.

“Most of the comments were people showing me love,” Ross said. “I really, really appreciate the kindness of people. Not just the money. I went through all the comments and almost all of them are positive.”

Cavallero said he posted that video of Ross because he respected him. He also could relate to him. Cavallero, who grew up in Pittsburgh and now lives in Maryland, started delivering for UberEats after he lost his job and needed to pay his bills.

“I used to want to be that guy who would get caught in a giveback video, where someone would walk up to me and be like, ‘Here’s $1,000!’” he said. “I was so broke. I wanted someone to bless me. But it’s amazing to be able to be the person blessing people. Now, I’m the guy who can put someone’s Cash App out there with a sincere story and use my platform to get them back on their feet.”

Since that video went viral, Ross and Cavallero have met for lunch. That day, they weren’t picking it up for anyone. They sat, talked and ate. Ross insisted on paying and, after much protesting, Cavallero let him.

“I felt like I had to do something for him,” Ross told me. “He really helped me out and changed my life because I was struggling.”

• Theresa Vargas is a local columnist for The Washington Post. Before joining the Post, she worked at Newsday in New York. She has degrees from Stanford University and Columbia University School of Journalism