Halle Bailey Seen at the Women's Singles Figure Skating Event During the 2026 Winter Olympic Games, Igniting Buzz Over Her Companion

The Grammy-nominated singer made an icy arena feel suddenly very warm when she stepped out in Milan with a very rakish actor by her side.

On February 17, 2026, Halle Bailey attended the Women's Single Skating Short Program during day 11 of the Milano Cortina Winter Olympic Games in Italy.

But while the skaters dazzled on the ice, her companion attracted the most attention. He's someone audiences already know very well as the Duke of Hastings, and after a trouble few years with her ex, many of Bailey's fans couldn't be happier at the possibility of a new relationship.

A Glamorous Entrance That Stole The Chill

Although the tournament was at the Milano Ice Skating Arena, Bailey did not dress for the cold. She dressed to standout.

Wrapped in a voluminous white shaggy faux-fur coat, the "angel" singer embraced full high-glam drama. The coat's long, wispy fibers and oversized collar framed her face beautifully. Underneath, she had a white outfit, featuring a buttoned top and short shorts. She was also in sheer pantyhose and white stilletos.

Even seated, she commanded attention. A striking ring with green and white gemstones flashed on her right hand whenever she applauded, paired with a white clutch purse and crisp white nail polish that completed the snow queen look.

Then there was the man seated beside her.

A Familiar Face In Neutral Tones

While Bailey opted for statement glamour, her companion leaned into structure and restraint.

Regé-Jean Page, best known to many as the Duke of Hastings in Netflix's "Bridgerton," wore a light beige utility-style jacket with a contrasting black collar and visible vertical stitching.

Large chest pockets added a casual edge, layered over a white turtleneck sweater that softened the look. Dark charcoal trousers grounded the outfit, keeping it sleek without trying too hard.

He and Bailey were seen talking throughout the event, leaning in close as skaters performed. A friend sat on the actress's other side, but it was the back-and-forth between the two A-listers that caught cameras again and again.

And fans noticed immediately. As photos from the Olympic outing began circulating online, the reactions were instant and enthusiastic.

One commenter wrote on Instagram, "They are fitting for each other." Another chimed in, "Baby girl raised her standards!! Good for her! Upgrade!!"

The buzz did not slow down on a second post, where one person gushed, "Best looking couple! 🥰🥰🥰." Another observed, "These two nearly look like family.. 😍"

"They look great together ❤️," read one comment. And perhaps the boldest message of all stated, "They are both so beautiful, just imagine what their children would look like 🤩."

Fans were not just casually intrigued. They were fully invested.

Of course, the actors may just be promoting their new rom-com "You, Me & Tuscany." But this appearance comes after a very ugly chapter in Bailey's personal life.

A Relationship That Made Headlines

Back in October 2024, it was announced that Bailey and rapper DDG, whose real name is Darryl Dwayne Granberry Jr., had split. The social media star shared a statement on Instagram Stories confirming the breakup.

"Dear friends and supporters, After much reflection and heartfelt conversations, Halle and I have decided to go our separate ways. The decision was not easy, but we believe it's the best path forward for both of us. I cherish the time we've spent together and the love we shared."

The rapper maintained that their love stayed deep and true even as their relationship changed. He also vowed that they would remained best friends who adored one another.

The former couple, first romantically linked in January 2022, welcomed their son Halo in late 2023.

While announcing their split, DDG even explained that they planned to concentrate on their separate paths and their duties as parents. He also sought compassion from the public as they navigated that period of change.

But things soon grew more complicated.

A Legal Battle That Turned Serious

In May 2025, Bailey was granted temporary sole legal and physical custody of her son, according to court documents obtained by People.

The outlet reported that the "Little Mermaid" star alleged physical and emotional abuse and was granted a temporary restraining order requiring DDG to remain 100 yards away from her and Halo. The order was set to expire at a court hearing scheduled for June 4, 2025.

In the paperwork, Bailey detailed several instances of alleged mistreatment and concluded her statement by explaining that she tried every possible alternative to avoid a legal battle. She also shared her realization that she could not satisfy or calm her ex, nor could she tolerate the ongoing cycle of abuse any longer.

But DDG tried to fight back.

In June 2025, a judge denied his request to prevent Bailey from taking their son out of the country. According to court documents also obtained by People, his emergency motion and request for a restraining order were both rejected.

He had asked the court to restrict international travel with their son, specifically a vacation to Italy. Bailey filed a request to deny his motion and to grant her permission to travel. Representatives for both parties did not immediately respond for comment at the time.