You’ve seen the headlines. You’ve probably seen the paparazzi shots of Jesse Williams walking through Rome or NYC. But honestly, trying to track a Jesse Williams relationship is like trying to follow a plot twist on Grey’s Anatomy—just when you think you’ve got the rhythm, everything shifts.
It's complicated. Really complicated.
The man who spent over a decade playing Dr. Jackson Avery has lived a life that is, in many ways, just as dramatic as the halls of Grey Sloan Memorial. Between a massive, multi-year divorce battle and a string of high-profile romances, Jesse Williams isn't just an actor; he’s a case study in how fame, family, and new love collide under the spotlight.
The Alejandra Onieva Era: Is It PR or the Real Deal?
Fast forward to late 2025 and early 2026. The internet basically imploded when photos surfaced of Jesse holding hands with Spanish actress Alejandra Onieva.
They were in Italy. Rome, specifically. They were there for the premiere of their Prime Video series, Hotel Costiera.
Now, some people are skeptical. You know how it goes—two attractive co-stars hold hands on a red carpet right as their show launches, and suddenly everyone smells a "PR stunt." But the chemistry? It’s hard to fake that kind of ease. They were spotted together in Milan before the premiere, looking way more casual than "business partners." Alejandra, who some might recognize from the Netflix hit Alta Mar, seems to be the latest chapter in Jesse’s evolving personal life.
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Moving on from Ciarra Pardo
Before Alejandra entered the frame, things seemed pretty solid with Ciarra Pardo.
They were together for years. Ciarra, a powerhouse creative director who has worked closely with Rihanna, was Jesse’s "longtime girlfriend." They were the low-key couple. You’d see them running errands in L.A. or grabbing sushi in West Hollywood, looking like a normal, albeit very good-looking, pair.
They even spent his 43rd birthday together in Paris during the 2024 Olympics. But as 2025 rolled on, the public sightings dwindled. Relationships in Hollywood often end quietly, without a big "we've split" Instagram post. By the time Jesse was seen in Italy with Alejandra, it was clear the Pardo chapter had closed.
The Aryn Drake-Lee Divorce: A Legal Marathon
You can't talk about a Jesse Williams relationship without talking about the divorce that seemingly never ends.
Jesse and Aryn Drake-Lee were together for thirteen years. They met when he was a schoolteacher in New York, long before the scrubs and the fame. They married in 2012. By 2017, the marriage was over, but the legal battle was just getting started.
It was brutal. Honestly, it was hard to watch.
- Child Support: At one point, Jesse was paying over $50,000 a month. That dropped significantly to around $6,400 after he left Grey's Anatomy.
- Custody: They share two kids, Sadie and Maceo. The court has seen countless filings regarding everything from vaccination schedules to FaceTime calls.
- Conflict: A judge even ordered them to attend a "high-conflict parents" program.
Even as recently as May 2025, Jesse was back in court. He was reportedly seeking more control over medical decisions for the kids. It’s a reminder that behind the red carpet smiles, there is a very real, very messy co-parenting struggle that has defined his life for nearly a decade.
The Dating History You Forgot About
Remember Minka Kelly? People went wild for that one. They dated for a few months in 2017 and 2018, right in the heat of his initial split from Aryn.
Then came Taylor Rooks, the sports broadcaster. That was a brief moment in the sun. And of course, there was Taylour Paige. They made their debut at a runway show in Harlem back in 2019 and were together for about three years.
Each of these relationships seemed to share a common thread: Jesse keeps things relatively private until he doesn't. He isn't the type to post daily couple selfies, but he also doesn't hide when he's happy.
What We Get Wrong About His Personal Life
A lot of fans think they know the "truth" based on a few court documents or a grainy photo. The truth is usually much more nuanced.
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When Jesse left Grey’s, he took a massive pay cut to do Broadway (Take Me Out). That move wasn't just about his career; it impacted his child support, his custody schedule, and his ability to see his kids. It showed a man willing to trade "easy" fame for artistic fulfillment, even if it meant more legal headaches.
People often paint him as the "villain" or Aryn as the "difficult" one. In reality, they are likely just two people who grew apart and are now trapped in a legal system that feeds off conflict.
What’s Next for Jesse?
If you’re looking for a takeaway, it’s this: Jesse Williams is currently in a "work-meets-play" phase. His relationship with Alejandra Onieva is the one to watch in 2026. Whether it lasts beyond the press tour for Hotel Costiera remains to be seen, but for now, he seems to be enjoying the international stage.
If you're following this saga, here are a few things to keep in mind:
- Watch the Court Filings: If history repeats itself, we haven't seen the last of the custody disputes. These filings often reveal more about his current status than any interview.
- Look for the "Hotel Costiera" Press: The way Jesse and Alejandra interact during interviews will tell you everything about their "vibe."
- Check Social Media (Carefully): He rarely posts about romance, but he does post about his kids and his work. That's where his heart is.
Jesse Williams continues to be a fascinator. He’s an activist, a father, and a man trying to navigate love under a microscope. It’s a lot for anyone. We’re just watching it happen in real-time.
Actionable Insight: To get the most accurate updates on Jesse's status, focus on reputable entertainment outlets like People or The Hollywood Reporter for verified legal news, rather than speculative "blind items" which often conflate his past relationships with his current reality.