9 Guys Mandy Moore Has Let Into Her Wild Heart (Excluding Jack Pearson)

Mandy's first serious relationship was with the That '70s Show star, whom she dated from 2000 to 2002. Their breakup wasn't exactly amicable, since Wilmer revealed intimate details about his romance with her and ex Lindsay Lohan during a March 2006 interview with Howard Stern. "The sex with Mandy was good, but it wasn't like warm apple pie," he infamously said about taking Mandy's virginity. The actress was obviously upset by his comments, which she called "utterly tacky," and Wilmer later apologized about the situation while speaking to BlogTalkRadio.com. It seems they've patched things up, though, since they post friendly selfies together from time to time.

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Mandy's romance with Brian was never confirmed, but rumors swirled that they had a brief relationship in 2002 when they cohosted the Miss Teen USA pageant, as well as a New Year's Eve event for MTV.

Mandy got together with Billy, who's most famous for singing the Pokémon theme song, at some point in 2002, but the exact length of their relationship differs. Billy claimed he dated Mandy for a while in an interview with DJ Mohan Gumatay, saying, "We were together for a year, her mother is strict, her mom is her manager, and her father is a pilot. I don't want planes crashing into my house." Mandy, however, told fans on her website's message board that their courtship was in fact much shorter. "Talk about bringing the past up. LOL," she wrote. "Yes. we met on the *NSYNC tour. I was 15, he was 17. It only lasted for a few weeks. What a talented singer he is."

The tennis star swept Mandy off her feet from 2002 to 2004, and though they were on and off, they quickly became one of Hollywood's mid-2000s It couples. In an interview with Teen Vogue writer Lauren Waterman, Mandy hinted at how Andy's constant traveling was putting a strain on their relationship shortly before they broke up for good. "There's a lot I want to do before I take the plunge. . . . The reality is that Andy has a limited time during which he can do his job, and he travels more than I ever would or could. He's on the road from January to November — who thinks about marrying that?" Although they eventually split, they remained close, and Mandy even attended Andy's fundraiser in 2006.

The "Candy" singer dated DJ AM for two months before going their separate ways in March 2007, but after they broke up, they kept in touch. When he was badly burned in a 2008 plane crash with Travis Barker, she made sure to visit him and had nothing but kind things to say about her ex until his untimely death in 2009. In 2015, she posted a touching note about him on Instagram, writing "This guy. One of a kind. Been on my mind a lot lately....I can still hear your laugh and oh man, I miss your hugs more than anything. Nearly 6 years and I'm still at a loss...#adam."

In December 2007, Mandy struck up a romance with indie rocker Ryan Adams. The couple wed in 2009 and kept their private life extremely private, refusing to speak about each other in interviews. After six years of marriage, they filed for divorce, citing irreconcilable differences, and a rep for the couple insisted it was "a respectful, amicable parting of ways." The same day the news was announced, Mandy joked about it on Instagram with a photo of a caution sign reading "Mercury in Retrograde. Proceed With Caution." "Message received. #thatexplainsit #theworst," she added in her caption.