Back in the golden age of pop, heartthrob Justin Timberlake was known as "trousersnake." No one knows who started the rumor. It might have something to do with the fact that his dating life was more like a revolving door of hotties before he finally settled down and got married to the uber gorgeous, Jessica Biel.
He has reportedly dated a number of A-list singers and actresses over the years, and even a backup dancer, too. Most JT fans will only get to date Justin Timberlake in their dreams, but the women on this list actually got the chance to date him for real, yo. And the pop star should get a Grammy for having such an impressive dating life.
Britney and Justin had known each other since they were Mouseketeers in the “Mickey Mouse Club.” But they didn't start dating for real until the early 2000s, and soon enough, they became pop culture's "it couple" in the blink of an eye. Many of us still recall the time when they both went to an awards show dressed in matching denim outfits. But their love was not meant to be and Justin said “Bye, Bye, Bye” to Britney.
Veronica Finn dated Justin in the late 1990s while he was still trying to get his music career off the ground. Finn was also in a band called Innosense. In an interview with Radar Online, she was quoted saying, “I was a girl version of Justin. We hit it off right away.” But their careers took them on separate paths, so they decided to call it quits. Plus, Finn was afraid that Justin would never be able to stay faithful.
In 1996, 16-year-old Justin Timberlake dated Fergie, who was much older than him. She was 23 at the time and was with the band Wild Orchard. At the time, this young cougar hound was on top of the world because he had landed a gorgeous “older” woman. But once his NSYNC career took off and he became famous, his relationship with Fergie fell out of sync. No pun intended.
All Justin could focus on when he was a baby-faced 14-year-old teen was Danielle Ditto. The lovebirds dated from 1994 to 1996. They reportedly were each other’s first in all sense of the word, which makes her one of the most important women for JT. But they also did teenage stuff like attend high school dances before they went their separate ways as if often happens with young puppy love.
Mila Kunis and Justin literally slept together or at least she did. But it’s not quite as romantic as you think. They were shooting the film “Friends With Benefits.” They were in bed, and Justin was supposed to kiss her shoulder and possibly her back. But they had been working a 20-hour workday and Mila was tired. So the bubbly actress fell asleep next to Justin. But that’s all she's willing to fess up, even though the media claims these two were dating at the time.
In early 2003, Justin redefined the term brief relationship with Staci Flood. She pulled some badass moves on one of his music videos, “Rock Your Body” and clearly made an impact on JT. While their relationship only lasted a few months, Staci never earned girlfriend status. But she did appear in other music videos and on Maxim and Lowrider magazines.
Justin wasn’t too heartbroken over his split with Staci Flood. That same year, he got busy with Tatyana Ali, the actress who played Will Smith’s cousin on “Fresh Prince of Bel-Air.” She had also been part of “The Mickey Mouse Club” where they met and was the opening act for NSYNC way back when. Clearly, JT wasn't ready to settle down yet. He was just getting started, in fact.
It was around the 2000s that Justin and Nicole Appleton got to know each other a lot better. The 19-year-old was soaring from the success he was earning as part of NSYNC. He and Nicole, who also sang and wrote songs and was in the band All Saints, were spotted several times in London, England. But she ultimately wound up being just another notch in his belt.
In 2011, Justin temporarily broke up with Jessica Biel and found comfort in the arms of Ashley Olsen, allegedly. Justin’s reps denied they were involved, but rumor has it that they were spotted at a polo match, a “Saturday Night Live” after-party, and even at the Greenwich Hotel.
The rumor mill suggested that Justin had been with “24” actress Elisha Cuthbert, but the truth was that they actually never dated. However, she may have inspired him to write the track for “What Goes Around... Comes Around,” after Cuthbert split from Justin’s business partner Trace Ayala, whom she was engaged to. The song was about a cheater who gets cheated on. Ouch!
In early 2002, Justin and Alicia Keys would go to each other’s houses to enjoy meals that reportedly included kissing and hugging. But a month into the rumored relationship, the musical talents went cold turkey and stopped hanging out. Maybe they got tired of each other, but no one really knows why they decided to call it quits way before they were an item.
In 2002, rumors suggested that Jenna Dewan was the other woman Justin was seeing while he was in a relationship with Britney Spears. At the time, she was one of his backup dancers and may have been the reason why Justin and Britney called it quits. After the split, Jenna became Justin’s rebound girl.
In 2003, Justin and Emma, aka Baby Spice, were spotted publicly kissing a few times while going out in London. And while the former Spice Girl didn’t really share any details about her time with him, Justin reportedly claimed he and Emma had been more than just good friends and that she was “really gorgeous.”
Justin and his “Bad Teacher” co-star Cameron Diaz had dated for about four years. During that time, they walked the red carpet and surfed together, too. But in 2007, they broke up and the media claimed it was all because of another starlet who starred in one of his music videos.
The woman who supposedly caused Justin and Cameron Diaz to split up was Scarlett Johansson, who appeared in his music video “What Goes Around Comes Around.” The two of them allegedly had amazing chemistry on and off-screen and were reportedly seeing each other even while he was dating Jessica Biel.
It supposedly happened in 2009 when people started assuming that Justin and our girl Riri were seeing each other behind Jessica Biel’s back. The fact that they did a music video collaboration for the song “Rehab” undoubtedly added fuel to the rumors. He also took Riri to the amfAR Gala, instead of Jessica. But in the end, we all know who won his heart.
Lindsay Lohan reportedly met Justin at a Hollywood party, and that’s when they had a brief fling. But it supposedly happened once and it was also while he was still with Jessica. The “Mean Girls” actress then lived up to the movie name by tweeting “where’s jb cheater,” referring to Jessica Biel. Then she tweeted, “Why do people cheat?”
Us Weekly reportedly claimed that Justin wasn't that faithful to Jessica Biel in 2010 because he briefly dated actress Olivia Munn at the same time as he was dating her. The two had met at a MySpace event. The NSYNC bad boy allegedly lied to Munn about his relationship status, so she had no problems hanging out with him in her hotel. Now, this may just be another rumor, but where there's smoke, there's fire.
In 2011, Justin allegedly had a thing with Olivia Wilde. The actress had also co-starred with him in the film “In Time.” They played mother and son in the movie, which sort of makes this kind of creepy. But rumor has it that these two were cozying up to each other at The Roxy in Los Angeles.
Jessica Biel became Justin’s girlfriend in 2008. And things didn’t start out quite so smoothly. Rumor has it that while they were still figuring things out in the beginning, JT was less than faithful to her. And regardless of whether the allegations were true or not, they broke up in 2011. But love conquered all and they got together again. And in 2012, the got hitched and lived happily ever after... we hope.