Dating History: Justin Timberlake

It's Gossip Time!

Hello and welcome to Gossip Time, a weekly guide to the stars by Allie Jones. Today we have a brand new installment of our monthly-ish column just for paid subscribers called Dating History. In Dating History, we explore the romantic pasts of some of the most interesting characters in the Gossip Time universe. Today’s honored subject: Justin Timberlake.

Which celebrity’s dating history would you like to discuss next? Please leave your requests in the comments.

Did you know that Justin Timberlake is still on tour? The WORLD tour, that is. The 44-year-old pop star memorably worried last summer that his Hamptons DUI would “ruin the tour,” but it turns out that was the only time people really talked about it. Timberlake still has to do 21 more dates across Europe this summer, until he plays his last show in Baku, Azerbaijan on July 28. Whee!

According to her Instagram, Timberlake’s long-suffering wife Jessica Biel is traveling with him for part of it. Though she was reportedly “disappointed” by her husband’s DUI, and though he has publicly cheated on her numerous times, she has yet to divorce him. What does the future hold? Let’s revisit Timberlake’s past for clues.

Fergie, dated from 1996 to 1997

Shortly after joining NSYNC, but before the boy band became a phenomenon, Timberlake briefly dated Fergie of the Black Eyed Peas. “One of my good friends was dating J.C. Chasez, and so we’d all hang out with NSYNC,” Fergie told Cosmo in 2006. “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.”

Timberlake and Fergie performing their hit “Where Is the Love?” several years after their initial romance

Fergie did not address the fact that she was 23 and Timberlake was 16 when the two got together.