Inside Justin Timberlake's Relationship History

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Britney Spears may be dishing the dirt on Justin Timberlake in her new book, "The Woman in Me," but Spears is not the only famous female who has shared secrets (or her bed) with the former *NSYNC hottie. Although he's been married to "7th Heaven" star Jessica Biel for more than a decade and the couple have two adorable sons, Timberlake's little black book was once a who's who of A-list actresses, singers, and celebrities. And who can blame them? The blue-eyed boy band turned solo artist turned actor is one of the hottest things to come out of Memphis, Tennessee, since The King himself. 

A triple threat of talent, combined with classic movie star looks, Timberlake has evolved from his cute "All New Micky Mouse Club" days to those *NSYNC hair years, to the matching denim misstep at the 2001 American Music Awards, to the suave "Suit & Tie" guy he is today. Along the way, he has had no shortage of women in his wake, and the rumor mills have linked him to a bevy of beautiful babes. How many of these rumored relationships were real? Timberlake doesn't seem big on the whole kiss and tell thing, but some have been notably public, while others may or may not have gone on behind closed doors. Either way, only the "SexyBack" singer and the women know for sure, but here's a look at some of his most publicized romantic entanglements. 

Name a hotter couple in the early aughts than Justin Timberlake and Britney Spears. Go ahead; we'll wait. One of the youngest power couples to hit the scene, these two appeared to have it all: good looks, hit albums, skyrocketing careers, and that whole prom king and queen vibe that stole America's hearts. Like a giddy schoolgirl, Spears told The Observer in 2001 that her boy band beau still gave her butterflies nearly two years in, adding, "As far as love is concerned, with him, too much is not enough. He's everything." Timberlake even admitted to GQ post-breakup that his infatuation with the blonde bombshell went all the way back to their "All-New Mickey Mouse Club" years. "I was in love with her from the start," he tells the magazine. "I was infatuated with her from the moment I saw her."

'Then, when it appeared that the dynamic duo was at the top of their game, it all came tumbling down. Amid reports of Spears' infidelity, further fueled by the now infamous "Cry Me A River" video, the couple called it quits with Timberlake allegedly breaking up with the princess of pop in a most surprising way: via text while she was filming the video for her hit "Overprotected." According to sources, Spears spills the deets on this and more in her memoir, which already has fans clamoring for her to give them more.  

While Britney Spears may have been his love at first sight, she wasn't Justin Timberlake's first crush. That honor belongs to none other than "Who's the Boss" star Alyssa Milano. Per Daily Mirror, Timberlake revealed in a 2016 radio interview with Rove and Sam that he had a poster of his fellow child star on the wall of his childhood bedroom. As an adult, the singer got the chance to make his boyhood dreams come true when he dated Milano for a hot second in 2002. He told the radio hosts, "My big crush was Sam in [television series] 'Who's the Boss,' Alyssa Milano. Then we dated briefly, so that got weird." 

For her part, Milano was a fan of the J.T. and Spears days, telling Entertainment Tonight, "They just seemed like the perfect match." But that didn't stop Milano, who was 29 at the time, from going out with Spears' 21-year-old ex just shortly after their split. She confessed to Us Weekly that she was actually waiting in the wings. "That was right after Britney broke his heart, I swooped in for the kill!" Alas, Milano and Timberlake's was not a "Charmed" relationship and eventually fizzled out. Milano went on to date a string of leading men, including Eric Dane, David Arquette, and Scott Wolf, to whom she was briefly engaged. Today, the "Melrose Place" actress is married to talent agent David Bugliari, and they have two children, a son, Milo, and a daughter, Elizabella. 

Some relationships start out with a bang. Others, well, with a burp. In one of the strangest meet-cute stories out there, the relationship between Justin Timberlake and Cameron Diaz began in 2003, when the 34-year-old blonde beauty presented the 25-year-old pop star with the Nickelodeon Kid's Choice Award for "Best Burp," an honor that Diaz had been bestowed with the year before. In addition to sharing a love of a good belch and a goofy sense of humor, Diaz and Timberlake seemed to share a passion for adventure. They were frequently photographed surfing, skiing, clubbing, and attending sporting events together, prompting Timberlake's friend Sharon Osbourne to tell People that the couple "are perfect together." Until they weren't. 

In 2007, the pair called it quits. Some suspected that the breakup may have had more to do with a rivalry between Diaz and Timberlake's "What Goes Around...Comes Around" video costar Scarlett Johansson, while others speculated it was his interest in Jessica Biel that caused the problem, particularly after a reported public argument at a Golden Globes after party shortly after the split.  Regardless, the duo remained professional, starring in "Bad Teacher" four years later. When asked if it was awkward, Diaz told Us Weekly, "No, it's great. Justin and I have always had a good laugh together, and to make a movie where we get to have a laugh together, and there really was no one else who was more perfect for this part."

It may seem like Jessica Biel and Justin Timberlake met, fell in love, got married, and lived happily ever after, but that's not the whole story. There was a moment in between meeting and marriage where the lovebirds were, to quote a famous "Friends" line, "on a break." Shortly after his split from Cameron Diaz, Timberlake was seen chatting up Biel at a 2007 Golden Globes after party hosted by Prince. Later, in his 2018 book, "Hindsight & All the Things I Can't See in Front of Me,"  Timberlake recalls that as a pivotal point in what would be his future. From an excerpt published in InStyle, he talks about that night. "Then the Golden Globes came up, and that's when we planned on seeing each other," he wrote. "We were both still seeing other people, keeping ourselves safe from getting hurt, from really putting ourselves out there. It took a bit for both of us to admit to ourselves that we were really, really into each other." 

As into each other as they reportedly were, the couple hit a rough patch and broke up in March of 2011. A statement released by reps for the power couple and published in People, reported, "Addressing the media speculation regarding Jessica Biel and Justin Timberlake's relationship, we are confirming that they mutually have decided to part ways. The two remain friends and continue to hold the highest level of love and respect for each other." 

In a weird Oedipus complex situation, following his split with Jessica Biel, Justin Timberlake was rumored to be dating Olivia Wilde, who played his mother in the 2011 movie "In Time." This was not the first time the pair had worked together (they were in 2007's "Alpha Dog"), but it was the first time that rumors of anything other than a friendship began to surface after they were reportedly spotted looking more than friendly while out on the town in Los Angeles. Perhaps it was the timing, given that Timberlake was still nursing his heartache over the Biel breakup, and Wilde had just filed for divorce from husband Tao Ruspoli, to whom she'd been married for eight years. Whatever the circumstances, Us Weekly reported the couple showed up at the Roxbury in white tees and jeans (what is it with Timberlake and matching his outfits to his girlfriends?) and partied until the wee hours.

An insider told the magazine that the duo was definitely giving date vibes, saying, "They were dancing, whispering, he had his hand on her back and shoulders and they were together all night." Wilde denied the rumors in a tweet saying, "Cool it, honeybadgers. We are just friends and have been for years." Only these two gorgeous costars know what really went down that night, but obviously, it wasn't enough to worry about since Timberlake reunited with Biel, while Wilde famously was last linked with heartthrob Harry Styles.