Jesse Williams Relationship History: All the Girlfriends and Children

Jesse Williams has a notable history of playing charming heartthrobs in film and television.

From his debut role as Leo in The Sisterhood of the Traveling Pants to his breakout part as the dashing plastic surgeon Jackson Avery in Grey’s Anatomy, and now his role as Tobert (that’s Robert with a T) in season three of Only Murders in the Building, Williams has consistently portrayed appealing characters.

In real life, the former school teacher is also considered a genuine heartthrob. However, his real-life love life mirrors the dramatic twists of his on-screen roles.

As a prominent TV star, Williams’s personal relationships often attract media attention. This was notably the case with his divorce from Aryn Drake-Lee, his partner of 13 years, and the subsequent extended custody battle over their two children.

Williams has also experienced other public leaks, such as the unauthorized release of photos from his Tony-nominated performance in the Broadway play Take Me Out.

Reflecting on the incident in a 2022 interview on Watch What Happens Live, Williams commented, “Everybody makes such a big deal. It’s a body. Once you see it, you realize it’s whatever. I just have to make it not that big of a deal.”

Despite such public scrutiny, Williams remains a significant figure, and many fans are interested in his dating life. While some of his romantic relationships have been kept private, others have been widely publicized.

Here is a detailed look at Jesse Williams’s dating history, including his current relationship status.

Jesse Williams and Aryn Drake-Lee (2004-2017)

Williams and real estate broker Aryn Drake-Lee first met in the mid-2000s when he was a schoolteacher in New York. After dating for over five years, they married in September 2012.

They welcomed their daughter, Sadie, in December 2013, and their son, Maceo, in October 2015. Their partnership extended into their professional lives as well, with the couple launching a production company called FarWord in 2012.

In a 2010 interview, Williams spoke about their supportive relationship: “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 thin. We know each other inside and out.”

Unfortunately, the couple divorced in 2017 after five years of marriage, citing irreconcilable differences. Their divorce was finalized in October 2020.

Since then, Williams and Drake-Lee have been engaged in a series of legal battles over custody of their children, with Drake-Lee seeking sole custody due to Williams’s demanding filming schedule.

They reached a custody settlement in March 2022 and continue to share custody of their children, though they have been advised to seek coparenting counseling to address post-divorce challenges.

Jesse Williams and Minka Kelly (2017-2018)

Williams and actress Minka Kelly first crossed paths while working on the video game Detroit: Become HumaN in January 2017.

Their relationship was confirmed in July 2017, amid ongoing rumors of infidelity related to Williams’s recent divorce.

In response to the speculation, Williams addressed the situation in JAY-Z’s “Footnotes for 4:44” visuals, saying, “I was in a relationship 13 years, 13 real years… All of a sudden motherf*ckers are writing think-pieces that I somehow threw a 13-year relationship… 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 private and reportedly ended it in January 2018. Neither party publicly discussed the reasons for their breakup.

Jesse Williams and Taylor Rooks (May 2018)

Williams and sports journalist Taylor Rooks sparked dating rumors in May 2018 when they were seen together during Memorial Day weekend at a Kevin Hart comedy show in Atlantic City, NJ.

The couple kept their relationship very private, and it is unclear when they parted ways, but it was before Williams began a new relationship in May 2019.

Jesse Williams and Taylour Paige (May 2019-2021)

Williams and actress Taylour Paige first generated dating rumors when they were seen together at the Sundance Film Festival in January 2019.

By May of that year, they made their relationship public at the Frieze art show in NYC and solidified it with a red carpet appearance at the Ozwald Boateng Harlem runway show later that month.

Williams and Paige had previously worked together when Paige appeared on Grey’s Anatomy in 2016.

In a joint interview in February 2021, they shared insights into their relationship, including Paige’s description of their first meeting as a romantic, almost predestined encounter.

They discussed their contrasting personalities and how it strengthened their bond, with Paige being more spiritually inclined and Williams being more practical and fact-based.

After more than two years together, Williams and Paige reportedly ended their relationship around mid-2021.

Their public appearances and social media interactions decreased significantly, and they eventually unfollowed each other on Instagram and deleted photos together, indicating their split.

Jesse Williams and Ciarra Pardo (2022-Present)

On June 15, 2022, Williams was spotted on a casual stroll with Ciarra Pardo in NYC. Pardo, who has worked as a chief creative officer for Fenty, and Williams appeared to have been friends before their romance, with photos of them together dating back to 2017.

Dating rumors about the pair began when they were seen holding hands during a lunch outing in June 2022.

While neither Williams nor Pardo has publicly confirmed their relationship, they have been seen together in public. Their latest appearance together was in June 2023 on a date night in LA.