Justin Timberlake's love life – Britney split drama, Spice Girls 'romp' and true love

Cry me a River singer Justin Timberlake has been with gorgeous actress Jessica Biel since 2007.

One of Hollywood’s hottest couples, they got engaged in 2011 and tied the knot at the stunning Borgo Egnazia resort in Fasano, Italy, the following year.

Since then, the pair have enjoyed marital bliss, eventually expanding their party of two to three in 2015 with the arrival of their first son Silas.

Three became four in 2020 when Justin and Jessica welcomed their second son Phineas.

In 2019, Justin took to Instagram to gush over his wife, calling her: “the most wonderful human I have ever met”.

“You make me smile, laugh, and love life more than I knew I could. I cherish every moment with you and can’t wait to spend so many more years doing the same… but, new”, he added.

But the 40-year-old wasn’t always the family fan he is today, well-known across the globe as quite the playboy back in the day.

Before the Friends with Benefits actor got hitched, he was linked with a string of celebs including Britney Spears, Cameron Diaz and Fergie – the Black Eyed Peas singer, that is, not Prince Andrew’s ex-wife.

And even since he’s been with Jessica, rumours that Justin has played away once or twice have done their seedy rounds.

These include alleged flings with Olivia Munn, Olivia Wilde, Ashley Olsen, and Scarlett Johansson.

Mr JT’s latest reported affair, with Alisha Wainwright, hit the headlines in 2019 after the Palmer co-stars were spotted holding hands in New Orleans.

Accusations of cheating aside, Daily Star takes a look at Justin’s dating history before Jessica.

Fergie

The Grammy winner briefly dated Black Eyed Peas singer Fergie between 1996 and 1997 before finding romance with Britney Spears.

The whole thing was a bit of a scandal, with Fergie coming in a whopping seven years older than 16-year-old Justin.

Not much else is known about their brief romance, but Fergie once said to Australia’s Courier Mail that soon after he got “real heavy with Britney”.

Britney Spears

The former NSYNC star began dating fellow former The All-New Mickey Mouse Club cast member Britney Spears in 1999.

Their dalliance was destined to be a pretty short one though, sensationally coming to an abrupt end just three years later.

This came amid reporters that she had been unfaithful to Justin, and when asked by Barbara Walters at the time, Justin said: “We’re not perfect. I don’t judge anybody. It’s just young love. It’s just young love. It was a very intense relationship, that’s for sure.”

He then released song Cry Me A River, which showed him stalking a Britney lookalike, catapulting him into superstardom.

Justin recently publicly apologised to Britney for his treatment of her at the time, claiming he was “deeply sorry” and wanted to “take accountability”.

The pair seem to be on good terms now as Britney has shared videos on Instagram of herself dancing to some of Justin’s songs.

Jenna Dewan

Justin started dating his backup dancer after breaking up with Britney in 2002.

Speaking with Andy Cohen in 2017, Jenna confirmed the romance on an episode of Watch What Happens Live.

She said: “We dated, not that long. We were like friends … that dated”.

Jenna went on to marry Step Up co-star Channing Tatum, welcoming daughter Everly with him.

Sadky, the pair split in 2019, a decade after they tied the knot, and she has since welcomed son Callum with new partner Steve Kazee.

Alyssa Milano

In 2002, Justin was also seeing Charmed alum Alyssa, who he later admitted he had a teen crush on.

The Trolls actor even revealed he had poster of Sam, her character in Who’s the Boss, on his bedroom wall!

Justin said to radio hosts Rove McManus and Sam Frost during the Trolls press junket: “My big crush was Sam in [television series] Who’s the Boss, Alyssa Milano. Then we dated briefly, so that got weird.

“I was like ‘hey, I used to be obsessed with you when I was a kid’.”

Cameron Diaz

The Memphis-born superstar and actress Cameron Diaz became an item in 2003 after he was briefly linked to Spice Girl Emma Bunton.

The pair met at the Nickelodeon Kids’ Choice Awards, and remained together until 2006, despite multiple rumours of splits.

They finally called it quits for real soon after Cameron introduced Justin as a musical guest on Saturday Night Live.

After the were reunited on-screen in 2011 comedy film Bad Teacher, Cameron told Us Weekly: “It really wasn’t a big deal. We had a great time and did the job, and we do what all actors do afterward. We all go our separate ways”.

Emma Bunton

Justin and Spice Girl Emma Bunton reportedly enjoyed a fling in 2003 while she was on a break from now-husband Jade Jones.

At the time, Justin reportedly told News of the World: “Emma’s really gorgeous. We’ve been together.”

The reported fling was said to have taken place before one of his Wembley gigs, with a source saying: “They met up at a secret London location for drinks. It looked innocent but that wasn’t the case. It got very heated.

“He made all the moves.”

Emma was grilled about the dalliance on This Morning, to which she replied: “I can’t say.”

However, the romance quickly fizzled out between them after Justin’s comment, with Emma telling 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.”

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Source: Celebrities - dailystar.co.uk