In 1998, Gosling enthusiastically revealed that he finally started getting leading roles at 17 years old.
"I've never played the hero or the cool guy. I've always been the loser, the goof, the geek, so just kind of getting used to that is weird. I like it, it's fun. I get to kiss the girl and win the fights, which is what I've always wanted to do," he confessed.
Just a few years later, Gosling was dating Sandra Bullock -- and a few years after that, his Notebook co-star, Rachel McAdams.
"I was like, 'Hey Rachel, we should go out. She was like, 'Oh, take off, you hoser. I'm not attracted to you, eh?' I'm like 'Oh, OK.' So that was how that worked," he laughed to ET in 2004 -- one year before he and McAdams stole the show at the 2005 MTV Movie Awards after winning Best Kiss.
By 2011, Gosling was dating another co-star, Eva Mendes, and while the pair (who share two young daughters) have remained private about their relationship, Gosling's mom has been a great stand-in at events.
One awards show companion Gosling wasn't so hyped about? That would be his former Mickey Mouse Club co-star, Timberlake.
"[Mendes] is at home with our girls," he explained to ET's Nancy O'Dell at the 2017 Golden Globes, adding that he wasn't "really" excited to be seated next to Timberlake instead. "It will be lovely to see him, but he's certainly no comparison. He'll understand."
Timberlake will be featured next week on When We First Met. Head over to Facebook and like When We First Met, so you don't miss any of the latest episodes!