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?!?


  1. lewzrb8be reblogged this from thereal90s
  2. jellysoap reblogged this from thereal90s and added:
  3. freesiafaces reblogged this from thereal90s
  4. goosebumpsfitsandmalaria reblogged this from thereal90s
  5. andarling reblogged this from thereal90s and added:
  6. tinytomato reblogged this from thereal90s and added:
    Brilliant! I had forgotten about this!!
  7. olympic--noodle reblogged this from thereal90s and added:
    Winona and Gwyneth were my favorite bff couple of the 90s! Remember when we all actually liked Gwyneth Paltrow?
  8. rachelanastasia reblogged this from thereal90s
  9. swipebook reblogged this from thereal90s
  10. thereal90s posted this