Matthew Wong, 32, first met Ford at the Corso Italia street festival in July 2013. The pair took one photo together then.
About a month later, Wong's partner at the time warned him she would outlive him if he didn't start taking better care of himself. Wong, who then weighed some 230 pounds, started counting calories, eating healthier foods and exercising more. Six months later, he trimmed down to 168 pounds.
One of his friends, inspired by a similar banana-for-scale meme popular on Reddit, urged Wong to take a post-weight-loss photo with Ford.
Wong emailed the mayor, explaining their first photo together and his dramatic weight loss since that time.
He said Ford's Cut the Waist initiative, which encouraged Torontonians to lose weight alongside the Ford brothers, Rob and councillor Doug, prompted him to start shedding the excess pounds. He congratulated the mayor — who said on his recent appearance on the Jimmy Kimmel Live show that he had lost some weight — on his recent success.
Then Wong got to the point.
"Mr. Mayor," he wrote, "I would really like it if we could get our pictures taken together again. This time as my 'after' photo."
Later, he admitted on Reddit that "I might have laid it on a little thick." But he says it was worth it, considering what happened next.
He has Ford's chief of staff to thank for setting up the second photo op. Dan Jacobs responded to Wong's request, simply asking him if he was available to come shoot the picture on April 7 at 4 p.m.
Wong provided CBC News with a copy of the email exchange.
Wong said he assumes Ford knew why they were taking the photo since he was so upfront in his email.
He says the mayor appeared jovial and was more than happy to pose for both pictures.
"He seemed impressed that I had lost 60 pounds," Wong said.
Wong uploaded the two images on Imgur and Reddit Monday night, using "Rob Ford for scale" as part of the title — which he admits he thought would be funny.
The image skyrocketed to the top of Reddit with more than 5,000 up votes and nearly 2,000 comments over four hours.
While Wong is surprised by how much attention the photo compilation has received, he's happy with his weight loss.