The WEDDING RINGERS

Ashley Hassard and Mike Di Carlo have modelled for multiple bridal photo shoots. Here’s what happened when they decided to get married at one

I had given up trying to date this man. He was just a unicorn.

ASHLEY HASSARD

Ashley Hassard and Mike Di Carlo grew up in Toronto but didn’t meet until they both went to Montreal as grad-trip chaperones-for-hire 12 years ago. “I immediately had a crazy crush on Ash,” says Di Carlo, 32, who was saddened to learn she was in a relationship. “We were able to share a pizza at midnight on New Year’s together and we were able to stay in touch through Facebook.” Once connected, the pair discovered they had a lot of friends, and even a strange bit of background, in common. “His mother and I were raised at the same daycare,” Hassard, 31, says with a laugh.

They each reached out to the other when they became single, but the timing didn’t work out for almost a decade. “I had given up trying to date this man,” Hassard says. “He was just a unicorn, and I was like, ‘Alright, if I can’t date him, I might as well be friends with him.’ ”

In 2017, the stars decided to align. “I had joined Soho House in Toronto, as a way to create a sense of community and get to know people,” Hassard says of the private social club on Adelaide Street West. “And I just invited him out. What was supposed to be a 20minute coffee turned into four or five hours. And it really was the best accidental date of our lives.”

Though it took a while for the couple to come together, things moved quickly once they did. “I genuinely moved in almost a week later,” Hassard says.

The pair, who co-founded the design and fabrication company Drawbox, Inc., decided to buck tradition from the start. “Ash helped me pick up the engagement ring way beforehand,” says Di Carlo, who managed to keep the timing of the proposal a secret, popping the question in October 2018 on a helicopter ride over Montreal. (He even saw her wedding gown beforehand, when she found it at LoversLand.)

They were planning to marry in August 2020 and secured a golf course just outside Toronto. But things changed when Hassard was shopping for a gown. At the first dress shop, Oh Happy Brides in the Junction, she hit it off with the owner, who mentioned she was hoping to get pictures taken of someone wearing her dresses. Since she and Di Carlo both modelled, Hassard volunteered, figuring it would be good practice for their own big day.

“We were both joking and saying, ‘I just really hope that shoot’s good, but not nicer than our actual wedding photos will be,’ ” Di Carlo says. Two days before the photo shoot, however, the couple had an unusual brainstorm.

“Still to this day, I have no idea whose idea it actually was,” he says, “which means we were both on the same page about getting married at the shoot.”

They sourced an officiant online, rushed the paperwork at City Hall, and each invited a friend as a witness. “Having never seen the dress, venue, hair or make-up beforehand, I went into the day as a complete and total surprise,” Hassard says. “Mike wore an old suit he happened to have in the closet.” They exchanged vows on set on July 16, 2019.

“We stepped outside for a10-minute ceremony, a few tears, and a couple of hours later we were at our favourite Mexican restaurant near our home,” Di Carlo says. “A bunch of tequila shots in and we were out cold by 11:30 on a Tuesday night. It was the best.”

A month later they gathered for a barbecue in Hassard’s mom’s Yorkville backyard, surrounded by 25 of their closest family and friends, ostensibly to announce their engagement. “We looked at each other and knew we couldn’t hold it in any longer,” Hassard says. “What was supposed to be our engagement party turned into a surprise elopement announcement.” They called off the August 2020 plans — but they’d soon be walking down the aisle again and again.

Since eloping, they’ve done seven more wedding shoots. “We’ve now had a formal wedding, a boho wedding, a really casual coffeehouse wedding and so many fond memories,” Hassard says, before Di Carlo jumps in to remind her of their beach wedding. The photos, Hassard says, have been used by bridal shops and designers. Their most recent shoot, with Elm Oak Studios, was a collaboration mainly used for social marketing.

One of the photographers they met during a shoot, Beata Mirowska of Bemiro Photography, even made sure Hassard took pictures in her original LoversLand dress, inviting them to come to the studio for yet another fake wedding shoot.

“I think traditions are wonderful,” Hassard says. “But if our relationship’s taught me anything, it’s when you know, you know.”