Rob Lowe and Sheryl Berkoff’s Relationship Timeline

Living their best lives! Rob Lowe and his wife, Sheryl Berkoff, have been happily married for more than 30 years — a rarity in Hollywood.

The couple first met in 1983 when they were set up on a blind date. While they didn’t initially hit it off, the Parks and Recreation alum and the makeup artist reconnected several years later on the set of 1990’s Bad Influence, which is where their romance blossomed.

The film may have been called Bad Influence, but the St. Elmo’s Fire star has frequently praised Berkoff for having an incredible, life-changing impact on him.

“[Our relationship] made me examine how I was living my life,” the “Literally! with Rob Lowe” podcast host told Haute Living in March 2014 of the beginning of his romance with the jewelry designer. “That led me to getting sober, which led me to changing my life — giving me everything I now have.”

Lowe has long been open about his battle with substance abuse, and he frequently discusses how being in recovery — he’s been sober for more than 30 years — has made his life rich and plentiful.

“One of the great gifts of recovery is that you start living your authentic life,” the Outsiders star told Variety in February 2021. “You start living your actual values and living as who you truly are.”

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Prior to dating, both Lowe and Berkoff had been in relationships with other famous faces.

The 9-1-1 Lonestar lead dated Melissa Gilbert for seven years between 1980 and 1987, proposing in 1986. The two called off their engagement, and the Little House on the Prairie star wrote in her 2009 memoir, Prairie Days, that she had suffered a miscarriage. “I had lost my baby and my relationship with Rob … and it hurt like hell,” she revealed. Lowe was rumored to have dated Winona Ryder from 1986 to 1988.

For her part, Berkoff reportedly dated her future husband’s fellow “Brat Pack” member, Emilio Estevez, in the 1980s. She went on to romance Keanu Reeves a few years later, according to Gwyneth Paltrow. The Goop founder was a teen on the set of a TV movie (starring her mother, Blythe Danner), when she first met the industry professional, who was doing makeup for the film.

“[Berkoff] was dating Keanu Reeves, who was my celebrity crush,” the Oscar winner told Lowe on his podcast in July 2020. “And she was so cool. … I just worshipped her. I thought she was literally the coolest chick of all time.” Paltrow isn’t the only one; the actor has done his fair share of gushing about his wife, as well.

Scroll down to see Lowe and Berkoff’s relationship timeline:

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Rumored to have been introduced by Estevez, Lowe and Berkoff met on a blind date, but nothing became of it until a few years later.

The couple began dating in 1990, after reconnecting while working on the set of Bad Influence.

The actor has been in recovery from substance abuse since May 10, 1990, and credits his romance with the jewelry designer as part of what led him to seek help. Lowe later told Entertainment Tonight that “[Berkoff] may have saved my life, really.” He continued: “I mean, she met me when I was at the end of my ’80s run of wild boy craziness and she was worth changing my life for.”

The pair tied the knot in the summer of 1991.

Lowe and Berkoff welcomed their first son, Matthew.

Two years after Matthew’s birth, the Sheryl Lowe Jewelry founder gave birth to the couple’s second son, John.

Rob revealed via Instagram that he and his family had to be rescued while on vacation in France after their residence was submerged with water due to heavy flooding.

Rob once again praised his partner in an interview with Haute Living. “Day in and day out, I choose to be with my wife,” he explained. “I know I’m never going to find anyone I love more, who’s sexier or a better mother.”

The West Wing alum celebrated the pair’s wedding anniversary via Instagram. “27 years ago today I was blessed (and lucky) to marry my gorgeous, smart, funny and powerful best friend Sheryl,” he wrote. “If you’d have told me then, what we would accomplish together, I would’ve never believed it. It continues to be a dream.”

When speaking about the “biggest influence” on his life, the Grinder alum told Men’s Journal, “It has to be my wife. We’ve known each other for well over 30 years, and the number of times where she has helped me make better decisions than I would’ve made on my own is innumerable.”

In addition to gushing about Berkoff on “Literally! with Rob Lowe,” Paltrow also revealed that the jewelry designer “taught me how to give a b–wjob, and you know, all the classic Sheryl stuff.”

The Shakespeare In Love star added: “It was so cool to have someone treat me like an adult and see me as like a young woman and someone who is sexual. She just made me feel so free.”

The actor surprised Berkoff with her “dream” of competing on Celebrity Family Feud. “Oh, I’m so happy!” she cried on set.

During an appearance on Jimmy Kimmel Live!, the movie star referenced those … skills Berkoff passed onto Paltrow — “Or, as I like to say, Chris Martin and Brad [Falchuk], you’re welcome,” he joked, referring to both the Glee alum’s ex-husband and current husband.

What better day than Valentine’s Day to express your love for your significant other? “I am so blessed to have this wonderful, surprising, inspiring, beautiful woman as my Valentine,” Rob shared via Instagram. “The best sweetheart I could hope for. Love you, Love Bug! Xoxox.”

“Happy Birthday to the love of my life,” the “Literally!” podcast host gushed in a sweet Instagram tribute to Berkoff. “You are the whole package, and I am blessed. Here’s to many more years of love and fun! Xoxo.”

The 9-1-1: Lonestar actor took to social media to celebrate over three decades of marriage with his love. 

“Happy 31st Anniversary, baby,” he wrote via Instagram on July 22 alongside a black and white photo of Berkoff. “Your love has made my world. You are as beautiful, knowledgeable, fascinating, kind, and hilarious as you were so many glorious years ago. Partners in love for life!!”