In 1990, Roberts starred in the movie “Flatliners,” where she met her co-star actor Keifer Sutherland. Sparks immediately started flying, and it was less than a year until the two got engaged. However, their relationship didn’t last, and the pair broke things off just three days before their wedding date.
This engagement only lasted for about ten months, so it was clearly not meant to be. On top of that, a day before the scheduled wedding, Roberts traveled to Ireland. She did that with the actor Jason Patric (Sutherland’s friend), and the two later had a short relationship that followed.
The Best of the Best
With an acting career in Hollywood that stretches over more than three decades, it's no surprise that Roberts has had the chance to work with the creme de la creme of the Hollywood gentry. She is one of the best faces in Hollywood and therefore, has been paired with no less than the best of the best.
Other than Richard Gere, Roberts's line of impressive co-stars includes Catherine Zeta-Jones and George Clooney ("Ocean's Eleven"), and most recently (“Ticket to Paradise”), Denzel Washington ("The Pelican Brief"), Brad Pitt ("The Mexican"), Owen Wilson (“Wonder”), Natalie Portman (“Closer”), and Tom Hanks ("Charlie Wilson's War").
Off-Screen Romance
Roberts has had a slew of hunky co-stars to play her characters' love interests. As it happens in the entertainment industry, sometimes their names have been romantically linked to hers off-screen life as well. Like many Hollywood stars, Roberts began mixing with her own kind of Hollywood icons.
In 1988 and 1996, she acted alongside Liam Neeson in the romantic comedy "Satisfaction" and the biographical thriller "Michael Collins" (respectively), and the two became romantically involved in real life following their on-screen involvements. Her subsequent dating pool was mostly comprised of actors such as Dylan McDermott, Jason Patric, and Matthew Perry.
Loving Lovett
In 1992, after seeing some significant ups and downs in her love life, Roberts was cast in "The Player." Working on this movie had a very unexpected ending, and Roberts got more than just a great role.
Her co-star in the film was country musician Lyle Lovett, in his very first film role, and we have a feeling you already know where this is going. Lovett and Roberts fell deeply in love. It was so intense that they were married in three weeks. Or shall we say eloped, because how can you possibly plan a wedding in less than a month?
But They Didn't Last
Allegedly, Roberts was a fan of his music before the pair met, and she would play his tapes in the early 90s. During their two years together, they co-starred in a second film together — "Ready to Wear" (1994). Roberts and Lovett's romance ended just about as quickly as it started. In fact, the two got divorced after only two years of marriage.
The assumption today is that the thing that broke the two apart was career pressures. Two Hollywood stars, each outdoing the other, we can confidently say that it wasn't meant to be. Luckily, it was an amicable split so there were no hard feelings when they ended things in 1995.