Actors, athletes and musicians, oh my! Hilary Duff has been a household name in the industry ever since portraying the iconic role of Lizzie McGuire on the Disney Channel Original Series, The Lizzie McGuire Show, so it shouldn’t come as a surprise that she’s dated some of the biggest names in the biz. Though the How I Met Your Father star dated the late Aaron Carter and her Agent Cody Banks costar Frankie Muniz in the early 2000s, one of her first headline-making relationships came in 2004, when she started dating Good Charlotte rocker Joel Madden when she was just 16 years old and he was 25. The pair split in 2006 after more than two years together. “It was so all-encompassing. It was so intense. It was my life,” Hilary previously said of their nearly 2.5-year relationship on “The Love Bomb Podcast,” hosted by her Younger costar Nico Tortorella. “It was like every minute of my day. It was pretty major.” The Cinderella Story actress went on to date former NHL player Mike Comrie in 2007, tying the knot with the professional Canadian athlete in August 2010. The pair welcomed their first and only child together, son Luca, in March 2012. Though the couple split in 2014 before finalizing their divorce in January 2016, they have remained amicable and are dedicated to coparenting Luca. “Mike is great. He’s still very close with our family, so I think it makes it easy for everybody to coparent or cofamily,” Hilary’s sister, Haylie Duff, exclusively told Us Weekly in April 2019, adding, “Because at the end of the day, it’s about Luca and what’s best for him and we love Mike.” The singer met her now-husband, musician and producer Matthew Koma, while collaborating on her Breathe In, Breathe Out album in 2015. “They had great chemistry in the studio,” a source close to Hilary told Us Weekly at the time. “Hilary thinks Matt is very talented and cute.” The pair made their red carpet debut at a pre-SAG Awards party in January 2017, and welcomed their first child together, daughter Banks, in October 2018. After the Winnetka Bowling League frontman popped the question in May 2019, he and Hilary wed in a low-key wedding held in their backyard in Los Angeles in December that same year. “I love this moment so much,” the Cheaper by the Dozen alum captioned a snap of herself and her hubby in honor of their first wedding anniversary in December 2020. “Matt and I were both too nervous to eat the day of our wedding .. this is directly after …. we slammed a plate of apps someone brought us before taking pictures and this pretty much sums us up … Snacking through life, dreaming about dinner at 7 am and wrangling kids. Oh, and dodging COVID the first year of marriage. Always with you babe. For you. Over and over I choose you and this [heart] thank you for being a damn good man.” In March 2021, Hilary and Matthew welcomed their second daughter, Mae, sharing a sweet snap of herself holding their new bundle of joy in a pool after a home birth with her family surrounding her. “We LOVE you beauty,” she captioned the black-and-white photo. Keep scrolling to see Hilary Duff’s complete dating history!