8. Joel Madden

You may not have been aware that Good Charlotte band member, Joel Madden, dated Hilary Duff when she was just 16 years old. Madden was 24 years old at the time. You will, of course, be familiar with Duff for her starring role in Disney’s Lizzie Maguire. A while back, the star talked out about her relationship with Madden, saying, “It was so all encompassing. It was so intense. It was my life,” Hilary said. “It was like every minute of my day. It was pretty major.” The pair dated for three years from 2002-2006. In December of 2006, Madden went on to meet reality star Nicole Richie, and the pair soon began dating and welcomed their first child together in January of 2008. The pair wed in 2010 and have been happily married since that point. Duff went on to marry Mike Comrie in 2010 and welcomed baby Luca in 2012. Unfortunately, the couple filed for divorce in 2015.

7. Naya Rivera

You probably never knew that Naya Rivera, who starred in the popular TV series Glee dated Kim Possible and Hounded star Tahj Mowry in high school. Apparently, they met on a print shoot when they were just four years old, and their moms became friends. They were in an on-again-off-again relationship for some time before Mowry ended things because “he needed to date someone more on his financial level,” revealed Rivera in her memoir, Sorry Not Sorry. The star also revealed that the two are still good friends, though. Also in the memoir, the actress revealed that Mowry was her first ever kiss. Aww, how sweet?

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