Hilary Duff and Mike Comrie’s Relationship Through the Years: How They’ve Evolved

Just a few weeks before giving birth, the former Disney star (seen here in L.A. in February 2012) kept up her sense of humor about her changing body. "No joke . . . When I get up, my massively pregnant morning walk looks like a 'walker' from The Walking Dead. #cmooooon BABY," she tweeted.

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Duff and hubby Mike Comrie welcomed son Luca Cruz Comrie March 20, 2012. Nine days later, the actress debuted her stunning post-baby style as she ran errands in L.A.

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The blonde beauty tweeted an adorable, black-and-white family portrait on April 12, 2012.

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Comrie and Duff headed out to a Coldplay concert together in Hollywood May 2, 2012. "So nice to have a night out, but we miss monkey!!!" she tweeted post-show.

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Luca, then two months in May 2012, looked pensive as he posed for a picture with his mom.

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"LOL he is cute when he's mad!" the proud mother tweeted to her 1 million–plus followers June 13, 2012.

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Three months after giving birth, Duff stunned in a sexy black two-piece on vacay in Mexico, on June 27, 2012 — but kept her adorable, sleepy son covered up in a swim shirt, trunks and floppy orange hat.

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Baby's first beach trip! Duff and Luca made the most of their time in Mexico with Comrie, Luca's aunt, Haylie Duff, and his grandma, Susan Duff. "Paradise!" the former Lizzie McGuire star tweeted June 28, 2012, sharing this snap taken on the sand.

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The singer toted an exhausted-looking Luca on their way to the airport in Mexico.

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On June 30, Duff took to Twitter again to share a major milestone with her followers. "Luca is cutting a tooth! It's the cutest/saddest (because it hurts). He's getting so big, my boy!" she wrote.

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Duff donned a citron cardigan to run errands in L.A. July 19, 2012, and little Luca matched his mom in a striped citron, gray, and blue tee.

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The Lizzie McGuire alum looked svelte and skinny in a striped dress with an embellished neckline during an outing at LACMA in L.A. The actress held the hand of her suit jacket–clad hubby and carried their son, Luca, who looked adorable in plaid, in another arm.

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Smile for the camera! Duff took pictures of her husband holding their son on a swing in Coldwater Park in Beverly Hills back in August. The two parents looked happy as they played with Luca outdoors, three years after they had tied the knot.

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The smiling couple attended a professional hockey game between the Nashville Predators and Los Angeles Kings at the Staples Center in L.A. Dressed casually, Comrie looked right at home in a black leather jacket and jeans with his arm draped over his sweater-clad wife's shoulder.

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Sunday fun-day! The adorable family enjoyed a nice breakfast in Old Town Pasadena with the actress' mother, producer Susan Duff. The blonde star looked happy and comfortable in a pair of glasses, charcoal-colored skinny jeans and burgundy sweater as she carried her adorable son in her arms. Comrie, meanwhile, looked casual in a sweater, jeans and hat as he carried the diaper bag.

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Disneyland darlings! The couple seemed happy when they took their son to Disneyland for the first time. Decked out in Minnie and Mickey Mouse ears, the mom and son posed happily beside dad, who wore a backwards hat on his head.

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Ringing in the new year together! Duff posted an image with Comrie on New Year's Eve of the two dolled up for an evening out. Wearing a short white dress with an elaborate fur stole, Duff looked demure and beautiful beside her bearded, suit-clad hubby. Less than two weeks later, they announced their split.

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Play time at a park! Three days before announcing their split on Friday, Jan. 10, the star and former hockey player took baby Luca to a park in Los Angeles, where they smiled and chatted outdoors on a rock. Calling the separation "amicable," her rep told Us Weekly, "They remain best friends and will continue to be in each other's lives. They are dedicated to loving and parenting their amazing son, and ask for privacy at this time."

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Her very own Modern Family! A month after announcing her split, Duff spent Valentine's Day in some tropical location with her estranged husband and their son. The former Disney actress posted a photo from their getaway and captioned the family pic: "#modernfamily #vacation #juicypear."

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After her split, Duff remained hopeful for a reconciliation with her husband — until it was reported that Comrie drunkenly hit on a waitress during one booze-fueled night out in Beverly Hills. According to one report, the former NHL hunk threw his money at the server and asked her for sex. A day after the report surfaced, Duff filed for divorce. 

A source close to the actress subsequently confirmed the report to Us Weekly, saying Duff "finally realized Mike wasn't going to change."

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Clues! Duff featured her estranged husband in a Flipagram message for their son, Luca, on his third birthday on March 20, 2015. "3 years buddy! 3 beautiful years! You make every minute worth while!" Duff captioned the video. "We cherish all your firsts and all that is to come. Happy 3rd birthday my love #timesflying #whatayear."

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Much better post-breakup. A wiser Duff told Cosmopolitan in her sizzling April 2015 cover story that she was ready for a new beginning. "I don't know if people are meant to be together forever. Things happen over a long relationship that you can't always fight," she shared. "I just always want to fight for happiness."

Still, she told the mag that she will forever cherish her memories with Comrie. "Mike and I were very in love when we met," the former Disney Channel star reflected. "We both really wanted to get married … Maybe it wasn't [the best decision], but we spent the majority of our time together really happy."

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Relationship goals, sorta! After a dramatic 2015, Duff revealed to Ellen DeGeneres on January 29, 2016, that she and Comrie were kicking off the New Year as friends. "We have such a great kid. And we’re both so obsessed with him," she noted. "We are good friends and we laugh a lot. And we have a great communication and we share pictures when one is not with Luca. He’s great, we are great and we keep on trucking."

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