Everyone Jesse Williams Has Dated Over the Years

Williams and real estate broker Drake-Lee reportedly first met in the mid-2000s while he was a schoolteacher in New York. After dating for more than five years, the couple tied the knot in September 2012. They welcomed their first child, a daughter, Sadie, in December 2013 and a son, Maceo, in October 2015. Their romantic partnership also extended to their professional lives, as the duo launched a production company called FarWord in 2012.

In a 2010 interview with USA Today, the “The Cabin in the Woods” star opened up about meeting Drake-Lee and the supportive relationship they’d built together. “I was a teacher when I met her, so she’s been with me through all different facets of my career. She’s stuck with me through thick and thick and thick and thin. We know each other in and out,” he said.

Unfortunately, the couple split up after five years of marriage, citing irreconcilable differences. According to court documents obtained by People, Williams filed for divorce in 2017, and it was finalized in October 2020.

The former couple share joint custody of their children, but over the years since their divorce, they’ve entered into a series of court battles as Drake-Lee sought sole custody of their kids due to Williams’s hectic filming schedule. They settled their custody dispute in March 2022, thankfully, and continue to share custody of their children (though the exes were recommended coparenting counseling to navigate postdivorce issues).

Williams met Kelly while collaborating on the video game “Detroit: Become Human” in January 2017. Following initial dating speculation, People confirmed their relationship in July 2017. However, the two were constantly subjected to rumors of infidelity, given their relationship’s proximity to Williams’s divorce from Drake-Lee.

The “Secret Headquarters” actor finally seemingly set the record straight when he appeared to address the cheating speculation in JAY-Z’s “Footnotes for 4:44” visuals. “I was in a relationship 13 years, 13 real years, not five years, not seven years – 13 years,” he said. “All of a sudden motherf*ckers are writing think-pieces that I somehow threw a 13-year relationship. Like, the most painful experience I’ve had in my life like with a person I’ve loved with all of my heart – that I threw a person and my family in the trash because a girl I work with is cute.”

Williams and Kelly kept their relationship very private for its entirety, reportedly splitting in January 2018. Neither party ever publicly addressed the reason.

Williams and sports journalist Taylor Rooks first sparked dating speculation in May 2018 after they were spotted spending quality time together during the Memorial Day weekend at one of Kevin Hart’s comedy shows in Atlantic City, NJ. In May 2018, Us Weekly confirmed Williams and Rooks were indeed dating. The pair kept their relationship incredibly private, so it’s unclear when they split, but it would have been before Williams moved on with someone new in May 2019.

Williams and actor Taylour Paige first sparked dating rumors when they were spotted being chummy at the Sundance Film Festival in January 2019. That May, the two attended the Frieze art show in NYC and confirmed their budding romance and further solidified their romance when they made their red carpet debut at the Ozwald Boateng Harlem runway show later that month.

Interestingly, Williams and the “Zola” star had already worked together long before they began dating when Paige appeared on “Grey’s Anatomy” in 2016. In a joint February 2021 interview with GQ, the lovebirds spilled many swoon-worthy details about their relationship. The 31-year-old actress recounted their first rom-com-worthy meetup at the Emmys party, saying, “I had a dream that I was sleeping next to him . . . It was just like, ‘There he is.’ Almost like, ‘Where have you been?'”

The duo also opened up about their polar-opposite personalities and how that strengthened their bond. “Jesse can be very literal – facts, facts, facts,” the “Hit the Floor” actor shared. “We came from very different worlds. She’s very feminine and into spiritual planes, astrology. I’m very practical, fact-based, and masculine,” Williams added.

“I was having a wild, unfamiliar, uncomfortable experience because it was all just happening in a very spiritual way – a way that’s not how I usually arrange things in my life. But I’d been going through a lot of transitions in life, and I had deliberately positioned myself to be open to saying yes, to be available to whatever, more than I had in the past. I don’t often let things happen to me. But because I had decided I was going to be open, I didn’t pull the brake like I normally would. I didn’t try to control, or position, or take a breath, and I just went along for the ride, as scary as that was and has been,” Williams said.

After more than two years together, Williams and Paige reportedly broke up sometime around mid-2021, as their joint appearances in public and social media dwindled. The pair even stopped following one another on Instagram and deleted their pictures together at some point, seemingly confirming their split.

On June 15, 2022, Williams was seen on a casual stroll with Ciarra Pardo in NYC. Pardo has previously worked with Rihanna as a chief creative officer for Fenty. Williams and Pardo appear to have been friends long before they started dating, as they’ve been photographed hanging out together as far back as 2017, like in the above photo from the Opening Ceremony x Made LA fashion show that year.

Speculation surrounding the pair dating first emerged when they were seen holding hands as they grabbed lunch in June 2022, leading many to wonder if they are romantically linked. Neither Williams nor Pardo has ever publicly addressed their relationship, but they also aren’t shy about being seen together in public. They were last seen in June 2023 on a date night in LA in photos obtained by Just Jared.