Skip Nav
Love It. Save Your Favorites Now.
The Justin Timberlake Facts Every Die-Hard Fan Should Know
View On One Page
Photo 4 of 9  
ADVERTISEMENT ()
4

His Exes

  • There's a reason he tended to date mostly stars. Back in 2011, he told Vanity Fair that he thinks celebrities find "refuge" in being with other celebrities, saying, "Why do you think we wind up dating each other, and feeling more comfortable around each other? We understand what it's like. 'Oh, thank God — finally, somebody who knows how I feel.'"
  • Even so, he didn't only date famous ladies. Soon after the 2002 release of Justified, he told Rolling Stone that he went on a date with a girl in Tennessee. They went to dinner, went back to his house, and watched a basketball game on TV.
  • Justin had three major heartbreaks early on. There were two breakups in his midteens, plus, of course, there was Britney Spears. He said of the three breakups, "They've all gone down the same way. All of them. Three strikes, I'm out."
  • After the Britney breakup, he called their time together "like something from a damn fairy tale" and he said, "I may not ever get over her . . . I do have to come to the realization that I might never."
  • Justin also felt there was "nothing normal" about him and Britney, and of their time together, he said, "We spent way too much time being the biggest thing for teenyboppers."
  • Although he toured with Christina Aguilera, the pair never dated. He did date Alyssa Milano, though, and he had crushes on Shannyn Sossamon and Natalie Imbruglia. Of the latter, he joked, "I'd like to start a rumor about me and her."
Previous Next

From Our Partners

Now You Know

Love Is Blind: Where Do Those Engagement Rings Come From?

Fashion

Everything to Know About the "Love Is Blind" Engagement Rings

by Sarah Wasilak 2/19

shopping

Oprah's Favorite Things List Has Major Gems, Including an Under-$100 Air Fryer

by Balim Tezel 11/06/25

Fitness

Paralympians Earn the Same Pay For Medals as Olympians, but Is It Enough?

by Karenna Meredith 8/29/24

health

How Often Should We Be Getting COVID Vaccines?

by Alexis Jones 8/23/24

Food

Pumpkin Spice Season Is Back Aug. 22

by Lauren Mazzo 8/21/24

Beauty

The Exact Red Lipstick Alexandria Ocasio-Cortez Swears By

by Alaina Demopoulos 8/20/24

health

What to Know About the Latest Mpox Outbreak, According to MDs

by Alexis Jones 8/16/24

health

Céline Dion Promised Her Children She’d Live: “They Already Lost a Parent.”

by Sara Youngblood Gregory 6/11/24

Latest Celebrity & Entertainment
We're Hiring! Write For Us Advertise With Us Accessibility Contact Archives
Power Your Happy
Terms Privacy Policy
©2026 Vox Media, LLC. All Rights Reserved.