"I love Toronto," he told The Canadian Press a decade ago, in an interview that was printed in the Toronto Star.
Praising the city as "cosmopolitan," he talked about the variety of people that live within Toronto and its nightlife — including its music scene and its restaurants.
"It's a real melting pot in every sense of the word," he said of the city.
In return, the city has loved him back.
When Prince played a show at the old Warehouse back in 1997, long lines of fans waited to see him play, just as they are doing today at Massey Hall.
"Very short, but very, very sexy, we love him," said one fan, who described the singer to CBC News while she waited outside ahead of the show, which was a warm-up for a longer tour.
In the early- and mid-2000s, he was married to a Torontonian. It was a pairing that led to Prince spending part of his time in the city.
He and Manuela Testolini would later split, filing a petition for divorce in July of 2006, according to People magazine.
Over the years, Prince has reportedly been spotted at Raptors games, or even taking to a stage on occasion — including as a DJ.
A Toronto Star feature story from April 2004 described the sequence of events that would typically occur before Prince would drop in to a downtown club. "Prince's security calls ahead, checks things out, then the singer takes a low-key spot, either alone or with his wife, and sips coffee, Amaretto on ice or Merlot through a straw," the paper reported.
If Prince indeed plays a rumoured "surprise" show in Toronto, he should be joined on stage by another woman with connections to the city.
Donna Grantis plays guitar in 3rdEyeGirl, the band that has recently been playing with Prince.
A bio on her website describes how Grantis moved to Toronto after earning a jazz performance degree at McGill University.
Living in Toronto, Grantis became an "in-demand studio musician," she went on tour and she fronted a band of her own.
She ended up joining 3rdEyeGirl after they came across her work on the Internet.