But the visit went well, their relationship blossomed and this year he proposed with a ring said to be worth $1-million. Paparazzi caught the moment - and one later when the couple was on a balcony apparently doing something provocative, which Comrie denies: "You realize you can't let your guard down."
Although accustomed to such scrutiny - before Comrie, she dated singers Aaron Carter and Joel Madden - Duff describes it as "so intrusive. I understand everybody's just trying to make money and stuff, but it's hard."
Then she adds, "Makes me want to move to Edmonton," which leaves her husband wide-eyed. Where to live is a touchy issue - and reportedly the cause of the spat between Nashville-based Underwood and Fisher, whose home is outside Ottawa.
Would they really move to Edmonton? "That's a loaded question," Comrie replies, with a nervous laugh.
But the Texas-born Duff, who was raised in California, has worked in Vancouver and Toronto, and says: "I miss seasons. That's what I love about Canada is having seasons, having snow for Christmas."
To which he replies: "You like seasons until you have them, year after year after year ... We still love L.A."
Comrie may be hesitant to go home because he has. Last year he rejoined the Oilers in a move that he, his agent and Kevin Lowe all describe as a bid to bury the hatchet.
It began well. In his first game, a preseason 4-0 win, he collected four points and got into a fight. The crowd chanted his name. "It was almost like a dream," he says.
But after that, he fought the flu and then mononucleosis, playing in just 43 of 82 games and able to do little to keep the Oilers from finishing dead last. "It was a tough situation because they were trying to play the young guys," he says, "and you don't want to go back and ruffle feathers."
The team's rebuilding process ruled out a new contract, so he dropped his price and shopped for another shot at the Cup - he was a Senator when Ottawa reached the finals the year he and Duff met.
The one-year deal in Pittsburgh pays the league minimum of $500,000 but reunites him with Sidney Crosby - they played together for Canada in the 2006 world championships - and evokes a bit of family history. The Penguins drafted his uncle Fred in 1973, although he never suited up for the team.
"I'm excited - it was definitely a hockey decision ... I wanted to go to a great team and be part of an organization like Pittsburgh," and, he confesses, "to be able to compete for a Stanley Cup."
The move east also will give him a break from the spotlight (in Pittsburgh even Crosby enjoys some anonymity) - he still seems genuinely surprised when the media pounced on the news that he and Duff have signed a prenuptial agreement.
"I don't think Mike looks at me like I'm a celebrity, and vice versa ...," Duff says. "It's just kind of like our jobs, and those things you learn to handle. You know, I'm in love with Mike. I love him."
For now, he focuses on his training, awaiting the solace of life in hockey and that gated community, where no lens can reach a balcony or dog park.
Barring a major injury, he can expect to play another five years. After that? He doesn't know.
He could go back to Edmonton and follow in the footsteps of his father and brother. After leaving hockey eight years ago, Paul Comrie also joined the family business and rose to become a vice-president.
"Yeah," the new Penguin says. "The problem is, I don't have the body to deliver furniture."