Although relationships in Hollywood often take unexpected turns, few have gripped the tabloids with the same fervor as that of Brad Pitt and Jill Schoelen.

Their relationship was actually clouded by betrayal, heartbreak, and an unexpected turn that shocked everyone.

Despite the fact that Pitt has a long list of notable films to his credit, including Troy, Mr. and Mrs. Smith, Legends of the Fall, and Once Upon a Time… in Hollywood, his personal life frequently receives more media attention than his professional endeavors.

Today, he is well known for his two notoriously publicized marriages, to Jennifer Aniston from 2000 to 2005 and to Angelina Jolie from 2014 to 2016.

Jill Schoelen and Brad Pitt

But did you know that Pitt was engaged to someone else prior to meeting Jolie and Aniston?

He met Jill Schoelen while still working his way up the Hollywood ladder, and this was a really strange short-lived love story for the Fight Club actor.

Jill Schoelen Dumped Brad Pitt For A Director?

The 1989 black comedy horror film Cutting Glass, which starred Jill Schoelen and Brad Pitt, debuted to negative reviews.

The film depicted Pitt and Schoelen as a high school couple, which may be where the ex-couple’s romance began. A short time after the movie, the two began dating, and things progressed pretty quickly.

Jill Schoelen and Brad Pitt

Also note that before Pitt, she dated Keanu Reeves, with whom she appeared in the 1986 film Babes in Toyland. Then, she reportedly became engaged to the Babylon actor for three months in 1989.

But why did Schoelen turn down one of Hollywood’s most eligible bachelors? Pit recalled in a statement to The Sun (via Cosmopolitan U.K.):

“She called me up in Los Angeles and was crying on the phone. She was lonely and there was a huge drama. At this point I had $800 to my name and I spent $600 of it getting a ticket from Los Angeles to Hungary to see her. I got there, went straight to the set where she was filming and that night we went out to dinner. She told me that she had fallen in love with the director of the film. I was so shocked I said, ‘I’m outta here.’”

Who Did They Date After Their Breakup? 

Jill Schoelen’s relationship with her director was short-lived; after their breakup, the actress married Anthony Marinelli (musician, composer, and conductor).

But she was married to Marinelli from 1993 to 2002. In terms of her professional career, she did not achieve the same level of fame as Brad Pitt after Cutting Glass, but she is recognized for her work in The Stepfather, The Phantom of the Opera, Rich Girl, and Popcorn.

Jill Schoelen

On the other hand, Pitt got engaged to Gwyneth Paltrow, his Seven co-star, after a highly publicized relationship that lasted from 1994 to 1997.

Then, in 1998, he started dating actress Jennifer Aniston; they got married on July 29, 2000. However, they declared their separation in January 2005, and two months later, Aniston filed for divorce, citing irreconcilable differences.

Following this, after seven years of dating, Pitt and Angelina Jolie alleged their engagement in April 2012. They later tied the knot on August 14, 2014, however, they got legally separated on April 12, 2019.

Brad Pitt

In terms of his professional career, Pitt will next be seen in Tim Burton’s upcoming fantasy comedy Beetlejuice 2, which is a sequel to Beetlejuice (1988).

Beetlejuice 2 will be released on September 6, 2024. Meanwhile, you can rent Beetlejuice on Apple TV.