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Celebrity Couples From the Past

66 Celebrity Couples You Most Definitely Forgot About

February 21, 2017 by Lauren Turner

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66 Celebrity Couples You Most Definitely Forgot About

There may be a short list of stars who've stood the test of time together, even in Hollywood, but not all celebrity unions are meant to last. Remember when Jennifer Aniston dated Tate Donovan and Penélope Cruz went out with Tom Cruise? How about Rachel Bilson's relationship with Adam Brody, or the time Alanis Morissette was engaged to Ryan Reynolds? Scroll through to see those duos and more surprising celebrity couples!

Sarah Jessica Parker and Robert Downey Jr.

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ewalsh 4 years

Great blast from the past.

Juiceee 5 years

I had no idea January Jones and Josh Groban ever dated.

annie6417 5 years

OMG!!! It's so funny and wierd as well, especially to see Brad Pitt, Matt Dammon and Heath Ledger...!!!

kimmieb124 5 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 5 years

Alanis and Ryan?! Mind BLOWN.

chocolate79 5 years

some of this is just very funny.... matt damon and winnona ryder! ha.. that's old school

jmhendricks88 5 years

I used to love Jake Gyllenhaal and Kirsten Dunst together. They were so cute!

popfaninMD 5 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 5 years

Colin and Busy??? ah ah ah! (terrible 90's or early 00's)

ModernGraceKelly 5 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 5 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 5 years

Each couple is more surprising than the last!

Anna-Monette-Roberts 5 years

Really funny and freaky!