When Hilary Duff was 19, she met Canadian professional hockey player Mike Comrie on a flight they were on to attend a vacation with mutual friends (via E! Online). At the time, she gushed about her then-new beau to Cosmopolitan, saying, "I love men who have a lot going on in their lives, like I do." In February 2010, Comrie popped the question with a $300,000 sparkler during a romantic getaway in Maui and by August, when Duff was 22, she and Comrie tied the knot. The actress spoke about her decision to marry at such a young age in an interview with Cosmopolitan. "I'd been working since the age of 11 or 12, so making that choice at a young age seemed right for me," she said.
In 2012, Duff tweeted the happy news that the lovebirds had welcomed a son, Luca Cruz Comrie. But, just two years later, in 2014, they announced their "amicable" separation, with a source close to the actress explaining that they'd grown apart and tried therapy, but decided they'd be "better as friends" (via People). In 2015, TMZ reported that Duff, whose son was just a toddler, had actually been the one to file for divorce. "I got divorced from Luca's dad when he was like 2," she told The Hollywood Reporter. "And then I would never introduce him to someone I was dating unless I was exclusively only dating them for like six months or more."
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