Skip Nav
Celebrity Couples
12 of the Most Extravagant Gifts Kim Kardashian Has Received From Kanye West
Celebrity Couples
Sarah Paulson Supports Girlfriend Holland Taylor at the Premiere of Her Broadway Show
Ellen DeGeneres
Ellen DeGeneres Sends Her "Average" Producer to Learn How to Dance Like Magic Mike
Around The Web
Join The Conversation
ewalsh ewalsh 3 years
Great blast from the past.
Juiceee Juiceee 4 years
I had no idea January Jones and Josh Groban ever dated.
annie6417 annie6417 4 years
OMG!!! It's so funny and wierd as well, especially to see Brad Pitt, Matt Dammon and Heath Ledger...!!!
kimmieb124 kimmieb124 4 years
I actually thought Katie Holmes and Chris Klein were a good match. Much more appropriate for who she was up until Tom Cruise came into the picture. They seemed sweet together. But Christina Applegate and Brad Pitt??? What? I missed that one.
curLRocker curLRocker 4 years
Alanis and Ryan?! Mind BLOWN.
chocolate79 chocolate79 4 years
some of this is just very funny.... matt damon and winnona ryder! ha.. that's old school
jmhendricks88 jmhendricks88 4 years
I used to love Jake Gyllenhaal and Kirsten Dunst together. They were so cute!
popfaninMD popfaninMD 4 years
ahhhhhhh. Popsugar is going THERE....LOL...Madonna and Sean Penn, Crusise and Cruz....Ahhh what could have been. I'm particularly fascinated you included Garner and Varten. I thought was buried in a vault some where. LOL
noonehere noonehere 4 years
Colin and Busy??? ah ah ah! (terrible 90's or early 00's)
ModernGraceKelly ModernGraceKelly 4 years
I remember Sandra and Ryan, because they did a movie together. He seems to date his leading ladies. I knew most of them, but some surprised me. I had no idea Edward Norton was engaged to Courtney Love. I just thought they went on a few dates.
dreamalittledream dreamalittledream 4 years
wow brad really takes on the style of whoever he's dating! He and Gwyneth look like twins!!! (Whether he's dressing like Gwyneth, a California/beach style or motorcycle man, he always looks good though!)
Allie-Merriam Allie-Merriam 4 years
Each couple is more surprising than the last!
Anna-Monette-Roberts Anna-Monette-Roberts 4 years
Really funny and freaky!
Neil Patrick Harris Family Halloween Costumes
Benedict Cumberbatch Sophie Hunter on Red Carpet Oct. 2016
Benedict Cumberbatch and Wife Expecting Second Child
Carrie Underwood at CMT Artists of the Year 2016 | Pictures
Barack and Michelle Obama at First and Last State Dinners
Kurt Russell and Goldie Hawn Laughing in LA October 2016
Biggest Celebrity Breakups of 2016

POPSUGAR, the #1 independent media and technology company for women. Where more than 75 million women go for original, inspirational content that feeds their passions and interests.

From Our Partners
Latest Celebrity & Entertainment
All the Latest From Ryan Reynolds