Brad Pitt and Jennifer Aniston had one of the most buzzed-about relationships in Hollywood history. From their ’90s dates (the matching looks!) to their five-year marriage and eventual split, it’s the couple we can’t stop analyzing. But in 2020, there’s actually reason to unpack this dynamic. They’ll be in the same room again this awards season for the Golden Globes and SAG Awards (he’s nominated for Once Upon a Time in Hollywood, she for The Morning Show). Plus, after reconnecting at Aniston’s holiday party last month, an Us Weekly source says the former husband and wife have a “wonderful connection that might seem flirtatious at times.” Below, a look back at the couple’s fashion when they were together and what happened to them after they broke up…then became friends again, years later.