Their relationship began when he asked her for money but ending up giving her 50p for her electricity meter, and on Saturday, Jack Richardson and Toni Osborne got married.
Big Issue vendor Richardson met Osborne in their hometown of Bristol in November 2013.
Begging on the street at the time, he asked passer-by Osborne if she could spare him any change.
But after she broke down in tears because she couldn't afford her electricity, Richardson ended up giving her 50p.
"It was just before Christmas and she burst into tears. She didn't have quite enough to put the lights on over Christmas, so I gave her enough to put the lights on," Richardson told the BBC.
Shortly afterwards, Richardson became a vendor for The Big Issue and they struck up a friendship as Osborne would regularly pass his spot.
"We began talking to each other every few weeks as she walked by. At first it was trivial stuff, but then we began sharing a lot and becoming quite close," Richardson told the Bristol Post.
When she learned that he was facing sleeping on the streets after the squat he was staying at was boarded up, she offered him the spare room in her house.
"When I went to stay with her we fell for each other," Richardson said.
In November last year, the couple were engaged.
"I didn't think anyone could possibly be romantically interested in someone who lived in a garage. Everything has changed," Richardson told the Post at the time.
"Essentially I've gone from being a tramp living in a garage, to living indoors with an amazing woman.
"I have never felt so intensely and deeply about anything before in my life. It's amazing."
The couple had originally planned their wedding to be "as cheap as possible" but were able to have their dream wedding thanks to kind support from local businesses and friends.
Local hairdressers Hobbs and Top Six Hairdressing, as well as a photographer and a videographer, offered their services for free. Avery's Wine Merchant donated champagne for a toast.
"An amazing person has even donated money for Toni to get a wedding dress. Then there's a guy I know, from the pub down the road, who is my size and has a box of Armani suits. He's very kindly offered to bring a few in for me to try and let me borrow one," Richardson told The Big Issue before the ceremony.
While Richardson and Osborne had thought they would marry in a registry office, they were able to have a church wedding after a vicar Richardson met at a soup kitchen offered to perform the ceremony free of charge.
Richardson said that help from the public turned their wedding into a "fairytale that we could never have imagined".
"I wanted to give my beloved the wedding she deserved but I couldn't. Thanks to the kindness of people I've now been able to," he told the BBC.
A spokesperson for The Big Issue said they were very happy for the couple: "It's lovely to have a good news story from one of our vendors."