Why Justin Timberlake And Fergie's Relationship Didn't Last Long

Before finding true love with Jessica Biel, Justin Timberlake was quite the eligible bachelor in Hollywood. As you'll probably remember, the former *NYSNC-er had a few high-profile romances before settling down and becoming a dad, famously dating the likes of Cameron Diaz, Alyssa Milano, and even Jenna Dewan, per Who Dated Who.

Of course, there was also that notorious romance with Britney Spears that stemmed from 1999 until 2002, with the two pretty much being the epitome of young's love dream. Well, until they weren't, that is. "I wish her the best, that goes without saying. We were two birds of the same feather — small-town kids, doing the same thing. But then you become adults, and the way you were as kids doesn't make any sense," he would later tell Vanity Fair in 2011 of their relationship. "I won't speak on her, but at least for me, I was a totally different person. I just don't think we were normal; there was nothing normal about our existence."

But there's another romance Timberland had with a famous female popstar that you may have forgotten about. Fergie! Yep, Fergalicious Fergie Ferg aka Stacey Ferguson. These two had a bit of a thing back in 1998 (pre her Black Eyed Peas days, if you're keeping count) but it just wasn't built to last.

Fergie opened up about what really went on with her and Justin Timberlake in 2006, admitting to Cosmopolitan that things were never serious between the two during their late 1990s dalliance — but that didn't stop them getting pretty hot and heavy! Fergie revealed that they met because one of her friends was dating Timberlake's *NSYNC bandmates, J.C Chasez, so she found herself spending a lot of time with the eventual "Cry Me A River" hitmaker. "Justin and I would go out together and have fun and make out. We went to Hawaii together, but we were never serious. He was Mr. Right Now," she explained of why things never went the distance.

But while Fergie was happy to dish back in 2006, she didn't seem quite so loose lipped when it came to Timberlake 11 years later when asked about their brief romance on "Watch What Happens Live." Host Andy Cohen asked her to reveal the best and worst thing about dating the former boybander, but Fergie responded, "It wasn't all that serious." She appeared to get a little flustered before adding, "Am I allowed to pass on this? Pass. Plead the fifth." Darn!

Though things were never serious between Fergie and Justin Timberlake, that didn't stop them from crossing paths again in the wake of their fling. After Fergie joined the Black Eyed Peas, she collaborated with Timberlake on their massive hit "Where Is The Love?" which (kinda awkward alert!) actually became what it was thanks to some angst brought about by another of his exes. Fergie's bandmate, Taboo, told "Talk of Fame" in 2009 that a lot of the song's rawness came about because of Timberlake's high-profile split with Spears. "We spend about eight hours [in the studio], six hours we spend talking because he had just broken up with Britney at that time. So we spent the whole time just building on the personal level, right?" he explained, adding Timberlake appeared to put all his emotions into the song.

The track went on to be a massive success for the band and is now considered one of their signature hits, but, as we know, it didn't exactly reignite a romance for the ages between JT and Fergie Ferg. Today, Timberlake is happily married to Jessica Biel and the couple share two children, Phineas and Silas, while Fergie went on to marry Josh Duhamel. Though they split in 2019, they welcomed a son, Axl, together and it seems like Fergie and Duhamel have been leading the way in amicable breakups and expert co-parenting ever since.