Angelina Jolie, Jennifer Aniston, and Gwyneth Paltrow are just a few of the famous people who Brad Pitt has been linked to, or married to.

But before he became famous, Pitt dated other well-known celebrities, including Juliette Lewis. They dated for three years before they called it quits in 1993.

In 2014, Lewis reflected on that time in her life and revealed to People (via Huffington Post) that the majority of the headlines she generated at the time were “usually about Brad Pitt or drug addiction, which hasn’t been me since I was 22. I’m 40. I quit all my bullsh** at 22. There is growth. Get out of the past. I used to be really insular, really introverted. I couldn’t articulate myself.”

While Lewis was having a hard time with all of the attention she was getting for her romance with Pitt, there was another Hollywood star around the same time who dated Pitt – Christina Applegate. She decided to unexpectedly dump Pitt before they were supposed to hit the red carpet of the 1989 MTV Music Awards together.

In 1989, Christina and Brad started dating. He was 25 while she was 17. They were still trying to establish themselves in Hollywood at the time.

She claimed that Pitt and television actor Jason Priestly used to visit her home in the Hollywood Hills for barbecues, as reported by More magazine (via USA Today). She recalled her carefree childhood and said, “All the moms kind of let us do whatever we wanted to do. There weren’t a lot of rules, but there was a lot of mutual respect. I always made sure she knew where I was, and I would always be home by a reasonable hour.”

She was also beginning to gain recognition for her performance as Kelly Bundy in Married…with Children.

Despite the fact that Applegate and Pitt were a rising golden couple in the world of celebrities, she allegedly dumped him on the red carpet at the 1989 MTV Music Awards.

The Breakup: Applegate revealed to Watch What Happens Live host Andy Cohen during a 2015 appearance that the rumors about her leaving Brad Pitt the night of the 1989 MTV Video Music Awards were true.

Andy posed some follow-up questions to Christina in an effort to extract some juicy details about the incident.

While Applegate did acknowledge that she left the awards ceremony with another man, she refused to identify him and instead tried to plead the fifth. She did, however, acknowledge that their relationship was totally over because she never met Pitt again after that evening.

Applegate reportedly left that night with a mysterious man who later revealed himself in another interview, despite the fact that she would not give any names or additional information about what transpired.

According to reports, he discussed the pair’s “brief fling” while promoting his memoir 18 and Life on Skid Row on the radio show Elliot in the Morning, saying, “[Christina] was interviewed recently on, like, Entertainment Tonight, or something, and they said, ‘What was the dumbest thing you ever did?'” and she continues ‘One night I ditched Brad Pitt for this other dude.’ And that dude would be me. So there was a time on this earth when Sebastian Bach was, like, a hotter lay than Brad Pitt.”,