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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!
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