2007

Hilary Duff

Duff's Dignity

Duff debuts a more grown-up, dance-driven single "With Love," kicking off her latest release, Dignity, which peaks at No. 4 on Billoard's 200 albums chart. On the film front, the actress-singer plays a European pop star in the satire War, Inc. alongside John Cusack and Marisa Tomei.

Hilary Duff

August

Duff Discusses Madden

After a newly brunette Duff makes PEOPLE's Most Beautiful list, she graces the cover of Seventeen and discusses her ex Madden. "I felt disrespected that he moved on so quickly," she says of Madden, who has a daughter with girlfriend Nicole Richie in 2008. "All of the going out he did after we broke up sort of shocked me...when we were together, he hated that stuff, so I felt like I just didn't really know him as well as I thought I did."

Hilary Duff

Hilary Hooks Hockey Player

With heartbreak behind her, Duff moves on with hockey player Mike Comrie. "I'm the crazy lady sitting in the crowd screaming my head off," she says of attending her guy’s Edmonton Oilers games. After two years together, Comrie pops the question to Duff while vacationing in Hawaii in February 2010.

2010

Hilary Duff

August 14

Just Married!

Six months after their engagement, Duff, 22, and Comrie, 29, tie the knot at Santa Barbara's Mediterranean Villa La Quinta in front of about 100 guests. "Mike held his arm around Hilary for most of the romantic, candlelit ceremony, and they both looked extremely happy," an eyewitness tells PEOPLE.

Hilary Duff

October 12

The Write Stuff

Duff adds bestselling author to her resume with the release of her young adult novel Elixir, the first book in a multi-part book deal for the former teen star. "I don't know if writing is really my strongest suit, but I know I have good ideas," Duff tells EW. She follows-up her debut with the sequel Devoted in 2011.

2012

Hilary Duff

March 20

It's a Baby Boy!

Duff, 24, and husband Mike Comrie, 31, welcome son Luca Cruz Comrie. "We are overjoyed and feel like the luckiest parents in the world," the new mom writes on Twitter. "He is surrounded by so much love!! Mom and baby are both doing extremely well."

2014

Hilary Duff

January 10

Splitting Up

Nearly two years after the birth of son Luca, Duff and Comrie announce their separation. "They remain best friends and will continue to be in each other's lives. They are dedicated to loving and parenting their amazing son," says a rep for the actress.

Photo Credits

BIOGRAPHY (top to bottom): Proya Productions; Jesse Grant/WireImage.com ; amazon.com; Courtesy Hilary Duff; Steve Granitz/WireImage

Edited by Julia Wang

Hilary Duff

Celebrity Central / Top 25 Celebs

 

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