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Justin Timberlake dated HER?

By on July 18, 2014

Justin Timberlake is one of America’s biggest singer-songwriter, actor, and celebrity. He was born on January 31, 1981 in Memphis, Tennessee, and has since grown to be one of the brightest stars in Hollywood. He’s best known for his chart-topping original songs, performance in the hit boy band NSYNC, and his first deal on The All-New Mickey Mouse Club. Not only has JT released a ton of hits, he’s been seen with a ton of girlfriends, too!

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Let’s bring it back to Girl #1. These two stars go wayyyy back. They met each other on the set of The All-New Mickey Mouse Club when they were just young kids. They started dating in 1999 and Spears later revealed that JT was her first kiss! The relationship only lasted until 2002 when Britney allegedly cheated on him! GASP! In 2011, Justin revealed he hadn’t talked to her since the break up! Even though it ended messy, they’ll still go down as Prom King & Queen of the early 2000s— which brings us to our rating of 1 /5(He can totally do better.)

Justin Timberlake and Britney Spears 2 Justin Timberlake and Britney Spears 1


Next, please! It’s rumored that Jenna Dewan-Tatum may have had a role in the TimberSpears break up, but that’s still unconfirmed. We believe they still had a fling in 2002, JT was in MAJOR rebound mode, so JD-T might have only been his rebound girl. :'( She was fine though, because she quickly dated Shane West, then moved onto her Step-Up co-star Channing Tatum, and they’ve tied the knot since. Needless to say, this one won’t get too high of a rating from us. I’ll say .5 /5.

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Next! Around the time Justin Timberlake came out with his hit song “Justified,” he is rumored to have dated Alyssa Milano. Sources say, one night, he played basketball with her for hours! Scandalous! We’ve been told that they made a really cute couple, but it wasn’t a thing long enough for us to see for ourselves. They dated/broke up in the same year as Jenna Dewan-Tatum. #ReboundGirl2 Our rating: .5 /5

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Next! From 2003-2006, JT was rumored to be dating Cameron Diaz from 2003-2006! They dated for a total three years before calling it quits! Diaz announced that it was because Justin had allegedly been cheating on her! That’s only a few years since Justin was cheated on by Britney Spears! In the words of Timberlake himself… “what goes around… comes around.” Our rating: a generous 1.5 /5!

Justin Timberlake and Cameron Diaz 2 Justin Timberlake and Cameron Diaz 1

On to the next one! JT was rumored to have had a quick scandal with Scarlett Johansson, around the time she was a feature in his new hit music video “What Goes Around… Comes Around.” There was never any confirmation from either of the stars, but there were several media speculations of a fling between them. Hmm? Do you think they were a thing? Our rating: 1 /5.

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Next! February 2007 marked the start of rumors stating that JT was onto his next girlfriend Jessica Biel. It’s no wonder they got together- they’re both gorgeous, talented, and rock the red carpet! Their relationship wasn’t just a fling… it went all the way from 2007 to March of 2011 when they called it quits due to (allegedly) a year of break up rumors that were just too much for the couple. It’s a bummer they broke it off- we loved them together! Because of that we give them a rating of 4 /5 (also it was so high because *SPOILER ALERT!* they get back togetherrrrrr! <3

Justin Timberlake and Jessica Biel 2 Justin Timberlake and Jessica Biel 1

Okay for this next JT gal pal we have to flash back just a little bit to during the Jessica Biel relationship. Yes… that means there were cheating accusations. US Weekly ran a story that accused Justin Timberlake of cheating on JBiel with Olivia Munn. Yup, this is the second time he’s cheated. They shared a room together for three days in New York for a MySpace event. Shame on Justin for cheating and shame on Olivia Munn for being his mistress! Because that is disgusting, they don’t get a rating.

Justin Timberlake and Olivia Munn 2 Justin Timberlake and Olivia Munn 1

Next! JT allegedly had a fling with Olivia Wilde, too! They were caught cuddling in the VIP of Hollywood Club around the time they were co-stars in In Time! It makes sense since both of the stars were fresh singles just out of relationships. It’s said that after the fling, they remained friends and never went official with their relationships. Since it was way too short and nothing happened, they get a MenWithStyles rating of 0 /5. Boo! #AnotherOneOfHisReboundGirls

Justin Timberlake and Olivia Wilde 2 Justin Timberlake and Olivia Wilde 1

Next, please! JT is rumored to have dated Ashley Olsen!!! They were caught canoodling around New York City together which led to more allegations that they had a fling in May of 2011!!! Neither Justin Timberlake or Ashley Olsen confirmed the rumors, but it’s up to you to decide whether you think it’s true or not!!! Either way, we think that it never would have worked out… That leads to a rating of, once again, 0 /5. Boo!

Justin Timberlake and Ashley Olsen 2 Justin Timberlake and Ashley Olsen 1

REALLY? We’re at… the last one! And… it’s none other than… wait? He already dated her… It’s JESSICA BIEL! It was reported that old lovers Jessica Biel and Justin Timberlake got back together after a short hiatus when they were seen on vacation together with Jessica Biel’s parents! They dated for round two just under a year when they officially tied the knot and got married in Italy in 2012! The wedding ceremony was absolutely astonishingly gorgeous and the Hollywood couple has been smooth-sailing since! In May, 2014, the couple officially announced that Baby Timberlake was on the way! We are so happy for the couple here at MenWithStyles and we wish that their parenting life brings them joy and love! Wait… Rumors in July, 2014 began to spread that the couple was reportedly calling it quits because JT’s website was hacked and he went on a rampage among other recent aggressive fits and Jessica Biel is apparently done! We’ll see how things turn out/ if it’s true or not.

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In conclusion, we’re happy for his happy ending and we wish him a long, exciting marriage/fatherhood with Jessica Biel and Baby Timberlake! Fun fact: He’s had more gal pals than Grammy Awards… and he’s had nine Grammy Awards… #GoJT

Until next time,


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