Justin Timberlake once has the nickname "Trousersnake" and judging by his past dating history - he certainly earned that kind of reputation. He has been linked to many A-listers in showbiz including Hollywood actresses, world-famous pop stars, super sultry models and of course, the odd back dancer or two. Fans can only dream of being able to date Justin, yet, for these women, that dream became an actual reality.
The notorious romancer told Glamour magazine, "There was a time when I had lots of affairs with women. I had to find out what I wanted. But basically, I prefer being in a relationship. But it's not very easy to have one - because I am under constant observation. The only solution to this is to keep mum about it."
He also joked, "I should not give anybody love advice."
It turns out that he hasn't been able to keep his past conquests as 'mum' as he would have liked and thanks to the internet, plus some very revealing interviews, it's easy to piece together his exact dating history. It's also safe to say that this is one man who deserves a high-five as he's had a pretty enviable run in his dating life.
16 He Said Jessica Biel Is His "Greatest Of All Time"
Justin really meant every word when he told Ryan Seacrest, "My wife is the greatest of all time." He didn't have it easy though as he also explained he was knocked back several times for a date, revealing, "I had to be pretty persistent in order to get her to say yes." The golden couple has now been together since 2007.
They have enjoyed a happy marriage six years now, and have one son together named Silas.
Jessica told Marie Claire magazine that it works so well because they have a lot in common. She revealed, "We have similar values; we believe in loyalty, honesty. We like to have fun. We like a lot of the same things. Also, in the business, we’re all very career-oriented, and you have to be a little selfish. I understand that about my peers — about being focused and driven — and if you can find that and someone who shares the same values as you, it’s like Score!"
15 He Broke Britney's Heart & Told Her "Cry Me A River"
There was a time when these two pop worlds collided and Justin and Britney Spears were an actual item. Their fan club went wild for the union, they were one of the most talked about showbiz couples on the planet and they also gave us them unforgettable matching denim outfits. So where did it all go wrong?
According to the Lifetime movie Britney Ever After, Britney allegedly cheated on Justin with her choreographer, Wade Robson. Shortly after their heartbreaking split, Justin released the track Cry Me A River where he finds himself in the home of a Britney-lookalike. Producer Timbaland also backed up that the song is about cheating as he told Dazed magazine, "I was like, ‘Man, don’t worry about it,’ and he was like, I can’t believe she did that to me’ and he (started singing), ‘You were my sun, you were my earth...'"
14 After His Split From Britney He Jumped To Her BFF, Alyssa Milano
Not long after this photo was taken of Charmed actress Alyssa Milano with her close friends Justin and Britney - the pop star power couple broke up. Alyssa told Entertainment Tonight, "They were super cute, super in love. They just seemed like the perfect match!"
Yet after the couple split, she hooked up with Justin, and they dated for just a few months. The actress said about her brief romance with Justin, "Everyone needs to get over it."
It's no surprise the two did hookup as Justin had a crush on her from a very young age. He said in an interview with Rove & Sam, "My big crush was Sam in (the television series) Who's the Boss, Alyssa Milano." The pair couldn't make it work though proving sometimes crushes aren't always that great in reality.
13 Justin Made Rihanna Feel "Wild"
The timeline of Justin and Rihanna's hookups together goes right back to the start of 2009. The Daily Star reported, "(Rihanna) said it was really good, hot, and wild and that they have some of the best [kissing] sessions she’s ever experienced." The source added, "She’s only out with the physical with him. And it looks like she got it."It's not unusual for Rihanna to fall for a singer as she's previously dated Drake, Travis Scott, and Chris Brown.
They were most likely set up by their mutual friends Jay-Z and Beyonce who are close to both the singers. Although it looks like it was just a fling between the two, they have remained close friends and are often spotted at parties together. All we're saying is Jessica Biel must be one seriously secure woman.
12 Scarlett Johansson And Justin Got Together When He Was On A Break From Jessica
What Goes Around Comes Back Around was the sequel to Justin's Cry Me A River - he clearly wasn't getting over the alleged cheating scandal anytime soon. For the music video, he decided to use Scarlett Johansson for the steamy kissing scenes in a pool, making him officially the luckiest guy in the world.
Then five years later, after Scarlett divorced her husband, Deadpool star Ryan Reynolds, she was spotted out on several date nights with Justin in New York City and were even caught by the paparazzi returning to his apartment.
This all happened during a time when Justin was on a break from Jessica Biel, who also happened to be Scarlett's co-star in the movie Hitchcock. Things likely got far too messy and complicated they both knew it was time to call it a day.
11 "Commitment-Phobe" Cameron Diaz Just Wouldn't Walk Down The Aisle
Justin and Cameron Diaz looked like a match made in heaven, but then after four years together they announced their surprising split in a joint statement. The reasons behind their split could have been that Cameron refused to commit. Justin sarcastically joked on The Ellen DeGeneres Show that if she wanted to buy a dress for their wedding "you’ll have to stay the same size for the next 15 years." Then when the Ellen also quizzed Cameron about hearing the sound of wedding bells, she replied, "I’m a commitment-phobe. Don’t want to do it.”
They split not long after the interviews but it turns out that Cameron isn't that against marriage after all. In 2015, three years after she split from Justin, she married Good Charlotte rocker Benji Madden.
10 Baby Spice Was Furious With Justin Over His "Kiss And Tell"
Emma Bunton a.k.a Baby Spice was at the height of her career with the Spice Girls at the same time NSYNC was the most popular boy band. So it was only natural for these two to hook up, and it's rumored they dated for a few months. Then things ended badly when Justin spoke to British tabloids about his relationship with Emma, and she was clearly not impressed.
She told the Daily Record, "I don't care if the papers say I'm still seeing Justin. I'm not.A lady should never kiss and tell and neither should a gentleman. That's all I have to say about him."
Adding, "It means I'm single again and I'm really enjoying my time with my girlfriends." Talk about Girl Power! Even if it didn't work out - she's clearly forgiven him and the pair are still close friends even today.
9 Jenna Dewan Ditched Justin For Channing Tatum
Channing Tatum and Jenna Dewan-Tatum both met on the set of Step Up but they remained just friends because she was dating Justin at the time. Jenna was asked by a fan on Watch What Happens Live about the romance and she admitted to a short-term fling. She met Justin when she worked as his backup dancer and admitted, "We dated…yeah. We were like friends, that then dated… no, I was not the rebound chick (from Britney).
Then in a shocking announcement - Channing and Jenna announced they have split after more than ten years together. In a joint statement, they revealed, "We have lovingly chosen to separate as a couple. We fell deeply in love so many years ago and have had a magical journey together. Absolutely nothing has changed about how much we love one another, but love is a beautiful adventure that is taking us on different paths for now."
8 Was He Really Caught Out With Olivia Munn?
One of the most shocking revelations that came out in the press involved Justin and actress Olivia Munn. An insider told US Weekly that the pair had exchanged numbers and he "started chasing her immediately." They spent some time going back and forth with some racy messages.
The insider added "(Justin) has been telling people it’s over with Jessica, even though the reality is he's just doing it behind her back."
According to the insider, the pair went to her hotel Gansevoort Park Avenue in New York City where "they were openly affectionate." When quizzed about the alleged affair, Olivia's reps said she doesn't "comment on her personal life." However, according to Life and Style magazine, their source also said, "(Olivia) is not stupid. She’s not expecting it to go anywhere - but she’d love it if it did!"
7 Fergie Said Justin Was Her "Mr. Right Now"
When Andy Cohen quizzed singer Fergie and her romance with Justin on Watch What Happens Live, he very nearly got the truth out of her. He asked what the "best and worst part" of dating the "Can't Stop The Feeling" singer is, and she rolled her eyes and revealed, "It wasn't all that serious. Am I allowed to pass on this?"
Clearly, she had a bit more to say when she sat down for an interview with Cosmopolitan magazine many years earlier. In 2006, she said, "One of my good friends was dating J.C. Chasez (from Backstreet Boys), and so we'd all hang out with 'N Sync. Justin and I would go out together and have fun and [kiss]. We went to Hawaii together, but we were never serious. He was Mr. Right Now."
6 Lindsay Lohan Named And Shamed Justin As One Of Her Many
So basically Mean Girls actress Lindsay Lohan decided to make very public a list of her conquests and Justin was one of those who had been named. The list which had 36 names also included James Franco, Orlando Bloom, Adam Levine, Heath Ledger, and Zac Efron. Someone had taken a photo of the list and leaked it to the press and Lindsay told the Daily Mail, "I had some friends over that I probably should have questioned a bit but I don't like to see the bad in people."
"Then someone must have stolen it and that's a really personal thing, that's something I would never do to anyone."
Star Magazine reported that Lilo had been with the "SexyBack" singer only once when the two met at a party in Hollywood for friends. It's also alleged that fling took place when Justin was with Jessica. Lindsay posted a tweet that read, "where's jb cheater" - meaning Jessica Biel - then added another tweet, saying, "Why do people cheat?" Both of those tweets were deleted and the drama ended soon enough.
5 He Still Had Chemistry With Olivia Wilde After The Cameras Stopped Rolling
Justin and Olivia Wilde met on the set of the sci-fi thriller In Time but there appeared to be more action off-screen than on. One onlooker at a Hollywood party revealed that the pair had been spotted cozying up together and they were "obviously a couple or on a date." Adding, "They were dancing, whispering, he had his hand on her back and shoulders and they were together all night."
Justin laughed to US Weekly about Olivia because she plays his mother in the film. He said, "We laughed about it when we first saw each other. First of all, Olivia is three years younger than me! We’d read the script and I would say, 'Here’s something my mom might do,' or 'Here’s the way my mom might say it.'"
4 Staci Flood Took The "Rock Your Body" Video Too Seriously
Justin sure has a thing for his backup dancers, and Staci Flood was no exception. Maybe it's that they spend so many hours together, that they are always on the road away from home, or that he only hires super beautiful women to shake it on stage with him - he just can't seem to keep his hands off.
Staci was his co-star for the "Rock Your Body" music video and they tried to enjoy a very hush-hush relationship.
A tour insider revealed to Flood magazine, "Staci has been seeing Justin for months. They don’t go out on public dates because she’s not Justin’s girlfriend - she’s his booty call. She’s willing to go along with it. She’s crazy about Justin, and she’s sure it’s just a matter of time before she wins him over completely." Staci was never granted girlfriend status and the pop star soon moved on after the tour was finished.
3 Tatyana Ali Was His First Popstar Princess
Before he was with pop princess Britney Spears - there was Tatyana Ali. This could be considered Justin's first showbiz romance as the couple was both emerging pop stars at the time they started dating. He dated the Fresh Prince of Bel-Air star in 2003 and she shared these adorable throwback snaps of them on tour together with the caption: Throwback Thursday. Touring w N'Sync back in the day. So fun. :)" She also tagged her ex-boo in the post.
A report from Pop Dirt at the time the pair were dating also confirmed, "(Justin was) cozy and cuddly at a Hollywood hotspot The Lounge with former Fresh Prince of Bel-Air star Tatyana Ali." We're sure these two have a lot of happy memories together if these cute pictures are anything to go by.
2 He Chose Danielle Ditto As His Prom Queen
Imagine being able to say that your date for the prom was Justin Timberlake. Well, that is a reality for Danielle Ditto who has full bragging rights to exactly that. They were both each other's first, and Danielle told the Mirror, "Of course, the first time was very scary and kind of awkward. But when you do something like that with someone you love, it’s incomparable."
Adding, "Justin was the perfect guy for it. He is sweet, gentle and thoughtful. It was almost like he was trained to be the perfect gentleman."
Danielle also revealed it was both their families that forced them to split up. Revealing, "Our families broke us up. It was terrible. We still tried to see each other when Justin came back (home). He would have to speak to a friend's house and I would hide behind a car."
1 But He Will Never Forget His First Love - Veronica Finn
Justin's first love was Veronica Finn and she was "the girl version of him." They dated between 1996 - 1999 when he was working with Disney and setting us a pop career and she was in a girl band called Innosense. Finn told Radar Online, "He was very special. Our love was unique, and he was an absolute sweetheart. I was a girl version of Justin. We hit it off right away."
She also revealed that she has a kept hold of a box of letters, cards, photos and other romantic items from their time together. The letters are said to be "sizzling" but she wouldn't dream of selling him out to the press. Sadly, the young romance had to come to an end when the couple went on separate tours, and she was paranoid he would cheat.
References: dailymail.co.uk, radaronline.com, mirror.co.uk
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