Love is certainly a mystery, isn’t it? If you were to look back at your own exes, I’m sure you’d have at least one person who’d make you go, “What was that? What was I thinking?!” I know I do. But all we can hope for from past relationships is a catalog of fond memories, life lessons learned, and maybe even a lasting bond between you and _____.
I wonder if these nine couples have that feeling. Do you think they look back fondly at these crazy vintage hairstyles and surprising Oscar® companions? I’d like to think so. Some of them are so adorable! And some are….quite interesting. Let’s go back in time to nine of the unlikeliest Oscar couples.
1. Brad Pitt and Gwyneth Paltrow
At the time, these two made perfect sense, didn’t they? Seeing them now however, reminds of how on Parks and Rec, Anne Perkins changed herself into a female version of Chris Traeger and he immediately got bored dating her because he was essentially dating himself. Remember the matching short blonde bobs? RIP Bryneth. (Don’t think they ever had a celeb couple name – but this fits, eh?)
2. Sarah Jessica Parker and Robert Downey Jr.
OH MY GOSH, look at this two! This looks more like a prom picture than an Oscar photo, but I’m kind of obsessed with it. Before SATC, and before Iron Man, there was SJP + RDJ = 2Getha4Eva
3. Christian Slater and Winona Ryder
I suppose it isn’t unlikely that the most beautiful actress of the ’90s dated the dreamiest actor of the ’80s and ’90s, but it’s always fun to take a trip down celeb nostalgia lane, don’t you think? The two briefly dated in 1988 after filming Heathers together. And then came Johnny…
4. Julia Roberts and Kiefer Sutherland
What the WHAT? I mean, I knew this happened, technically, but it’s still such a surprising pairing. What did they talk about? Was it a classic case of ‘bad boy chases after the good girl’? Oh, Jiefer, you still baffle me.
5. Ben Affleck and Jennifer Lopez
I actually rooted for these two. She was Jenny from the Block after all! But alas, the NY girl and the Boston boy couldn’t make it work. Considering Ben’s love of the Red Sox, it definitely makes sense. #GoSox, and farewell, Bennifer.
6. Madonna and Michael Jackson
Though their love only lasted one week, it began at the Oscars! A match made in pop star heaven, many wondered if it was a publicity stunt. WHO CARES? It was a magical celeb moment, now frozen in time. One that we can always look back on. Fake or real, this was a surprising, but spectacular Oscar pair!
7. January Jones and Josh Groban
Well hello, Ms. Jones! My, how Betty Draper has grown. Groban looks the same though. Still swoon-worthy with those curls. Did anyone else know this coupling occurred?
8. LeAnn Rimes and Andrew Keegan
You would think with the number of times I scribbled, “Mrs. Chrissa Keegan” on my diary that I would’ve kept myself apprised of every one of his lady-friends. This one slipped past me though. And I gotta say, even as a married adult woman, this one bothers me a little. Back off, LeAnn!
9. Cher and Val Kilmer
Nothing Cher does really surprises me at this point. Same goes for Val Kilmer. They both have that ‘wild card’ vibe that’s so strong, it practically punches you in the face. They dated in the ’80s and she was 14 years older than him! We’ve been making Demi/Ashton jokes for how long? And Cher was the original celeb cougar. Way to go, girl.
Can’t wait to see how many new Oscar couples show up this year! Make sure you join our Oscar Night Twitter Party, Co-hosted by the lovely Shay Mitchell (@shaymitch)! Red Carpet coverage starts at 7pm EST / 4pm PST and we’ll be tweeting about the dresses, the speeches and all the other fun moments in between.
1. Best Red Carpet Pose
2. Best Fake Cry
3. Best Surprise Face
4. Best Framily Photo
Follow these hashtags to join the conversation: #Framily, #HGparty, and #Oscars!
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