Tom Cruise and Cher — what the hell would these two even have to talk about together? The two apparently met at Madonna and Sean Penn’s wedding.
Cher e Tom Cruise pic.twitter.com/mj0yarWo28— 𝙴𝚜𝚝𝚎𝚛 𝙾𝚕𝚒𝚟𝚎𝚒𝚛𝚊 🤯 (@_ester_oli) January 20, 2020
John Cusack and Neve Campbell — This is weird, although the weirder pairing was John Cusack and Hillary Clinton’s chief of staff Huma Abedin or John Kerry’s daughter, Alexandra Kerry, but I don’t have any photos of those pairing, so we’re going go with Neve.
Nic Cage and Sarah Jessica Parker — It was brief, but before Sarah Jessica Parker married Matthew Broderick, she dated Nic Cage, though she broke that off to date John F. Kennedy, Jr.
Gina Carano and Henry Cavill — Before she went full, deranged Trumper (or at least, before she stopped hiding it), Carano dated Cavill for a full two years.
Chris Evans and Christinna Ricci — Evans’ relationship with the Addam’s Family star was actually a rebound off of Evans’ five-year relationship with Jessica Biel.
Will Arnett and Penelope Ann Miller — Whenever I think about these, “Oh, they used to date” stories, the marriage of Will Arnett and Penelope Ann Miller is what I always think of first. Miller was also involved with Al Pacino (makes sense) and Woody Harrelson (less so). We don’t have any photos of Penelope Ann Miller and Arnett, but here’s one with Harrelson, as well as a photo of Harrelson with Carol Kane (header), as those two also dated.
January Jones and Ashton Kutcher — Kutcher was Jones’ first boyfriend after moving to Hollywood, and according to her, he was kind of an unsupportive dick to her.
Bradley Cooper and Zoe Saldana — Bradley Cooper dated Renee Zellwegger for two years not that long ago (11 years ago), but their lives have gone in such different directions that it feels weird that these two were once a Hollywood couple (weirder still, Cooper was married briefly to Jennifer Esposito). After Zellwegger, Cooper dated Saldana for over a year, and they’d broken up by the time they starred together (sort of) in Guardians of the Galaxy.
Matthew McConaughey and Janet Jackson — They went out to dinner.
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