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Rob Lowe and his wife Sheryl Berkoff are one of the longest-lasting celebrity couples in Hollywood. The pair have been married since 1991 and share two sons together. At this point, it’s clear that not many people can imagine them being with anyone else.

However, it might come as a surprise that before Berkoff fell for Lowe, she was romanced by a few guys in the film industry — one being the actor’s St. Elmo’s Fire co-star.

Rob Lowe and Sheryl Berkoff
Rob Lowe and Sheryl Berkoff |Arnold Jerocki/WireImage

Sheryl Berkoff dated Emilio Estevez in the early ’80s

A few years before falling in love with Lowe, Berkoff was romantically involved with his St. Elmo’s Fire co-star and best friend, Emilio Estevez, in the early ’80s.

Though it’s unclear how the two met or long they were together, a 2009 piece published in The Guardian said the entire situation was “terribly incestuous in a glamorous, Hollywood sort of way.”

After calling it quits from Estevez, Berkoff dated actor Keanu Reeves for a time in the late ’80s. However, the relationship between them didn’t last very long.

Sheryl Berkoff and Rob Lowe fell in love while working on a film together

Following her romance with Reeves, Berkoff started dating Lowe, whom she met a few years prior.

According to Bustle, the pair met on a “half blind” date back in 1983. Though they went on a few dates after that, both weren’t ready to be in a serious relationship. The two ended up not seeing each other again until 1989, when Berkoff was Lowe’s makeup artist on the set of his film Bad Influence.

Two years later, in 1991, Lowe and Berkoff got married. Though Lowe had suffered from alcoholism, unfaithfulness, and had an infamous sex tape scandal under his belt, Berkoff helped him overcome those obstacles.

Now, he’s happier than ever.

Rob Lowe and Sheryl Berkoff
Rob Lowe and Sheryl Berkoff | Diane Freed/ Getty Images
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“I had met my now wife, Sheryl, and was attempting my first try at monogamy — which was not really in my nature at the time — and I wasn’t able to do it,” the 9-1-1: Lone Star actor told Haute Living LA in 2014.

“It made me examine how I was living my life,” Lowe continued. “That led me to getting sober, which led me to changing my life — giving me everything I now have.”

Rob Lowe and Sheryl Berkoff are still happily married

After tying the knot, Lowe and Berkoff went on to have two sons together: Matthew Edward Lowe (born 1993) and John Owen Lowe (born 1995).

Today, the pair are still happily married.

While long-lasting relationships are rare to come by in Hollywood, Lowe and Berkoff have found the key to maintaining a successful marriage, which the actor revealed during a 2019 appearance on the Goopfellas podcast.

“People always ask, ‘Do you have any advice about marriage?’ and I’m reminded of when they asked Alfred Hitchcock about making a hit movie. He said, ‘It’s all about the casting,’ and that’s the same with marriage,” Lowe said. “It really is all about who you pick. I always say to people, ‘If there’s any way to marry your best friend, do it.’ ‘Cause the rest of it comes and goes, and I was very lucky there.”