In the mid/late 90s Gwyneth Paltrow and Winona Ryder were BFFAE, with totes teenage girl best friend vibes..I love that they were dressing the same, with matching short haircuts and bad mid-length slip skirts (more VERY REAL but not-so-cute 90s fashion!) At one point they were double dating male BFFAE duo Ben Affleck and Matt Damon (Gwyn n Ben, Matt n Winonna) and I always always thought they had the pairings wrong- doesn’t Matt Damon seem way more Gwynnie than Nones?
Anyways, my favorite moment for the 4 of them was the Golden Globes in 97 (?) when they were all clearly wasted and having the best time ever. Every time they said Ben & Matt’s names for nominations, the girls were giggling and clearrrllyyyyy drunktown. I bet they were pretty fun to hang with back then. None of the relationships lasted very long, G & W had an alleged falling out over Shakespeare in Love and after breaking up with Gwynnie, Ben Affleck created the monster that was BENNIFER. But still…it was a golden 90s moment for a while there, celeb couple-wise.
Gwyneth had a pretty epic list of 90s boyfriends, best probs being Brad Pitt (matching haircuts) and Winona obviously never did better than Johnny Depp (Winona Forever!) but I don’t care- have a real soft spot for that foursome. Who does WInona date now?!?