#TBT 2003: Remember When Demi Moore Made Cougars Cool?

Once upon a time, Ashton Kutcher tricked celebrities on television and helped make trucker hats a national epidemic. From his shaggy hair to his dopey grin, Kutcher was very much considered a Hollywood prankster — who just so happened to win the affection of a woman 15 years his senior.

The Punk’d star began dating Demi Moore in 2003, and together the duo shocked fans and inspired a slew of pro-cougar trend pieces. We know, it’s hard to accept this considering he’s currently engaged to and expecting a child with Mila Kunis, but 11 years ago he was prime red carpet arm candy belonging solely the flawless Ms. Moore. I Love The 2000s is breaking down their glorious relationship — including the stepchildren and one overly chill ex who was always down to hang — in hilarious fashion, as well as the entire decade, year by year. Get nostalgic with us! Tune in when the series premieres on Tuesday, June 17.