Britney Spears' Sons Pose With Jamie Lynn's Daughter Maddie in Rare Family Photo

Britney Spears’ kids made a rare appearance on social media.

Sean Preston, 20, and Jayden James, 19 — the pop star’s sons whom she shares with ex-husband Kevin Federline — stepped out for to cheer on their cousin Maddie Watson, 17, at her high school baseball game.

In a heartwarming photo shared on Instagram on September 17, Maddie — daughter of Jamie Lynn Spears and Casey Aldridge — smiled in her athletic gear, even with her right arm in a sling. Standing proudly with her were Sean, Jayden and her little sister, Ivey Watson, 7, whom Jamie Lynn shares with husband Jamie Watson.

The cousins kept things casual for the big day. Sean rocked a fitted white tee with baggy jeans and a pair of headphones hanging around his neck, while Jayden went with an oversized beige T-shirt and dark denim.

Maddie sported her sash, while Ivey held onto a stuffed toy. Behind them, a banner read, “We Love You Senior 2025.”

The family outing comes as Britney works on repairing her bond with her boys after years of ups and downs. Despite long-standing concerns about her mental health, insiders said she’s been making progress in reconnecting with Sean and Jayden.

“The boys are maturing, and they want their mom in their lives, and Britney is really happy about that,” one source told a news outlet. “She’s so grateful to have them in her life. She feels whole again.”

Jayden, in particular, has been spending more time with the “Sometimes” star.

Between January and April, he stayed at her Los Angeles home.

“He always knew they’d find their way back to each other eventually, but he’s grateful that it happened sooner than later. They fell right into the swing of things like the old days,” a second insider said.

Sean, however, has been more cautious about making amends with his mom.

“[He and Britney are] slowly building more trust. Britney respects his wishes and is being very thoughtful of his [feelings],” the first source explained. “They’re focusing on communication without judgment of one another.”

The insider added, “They’ve both been through different challenges with Britney. Jayden’s healing process is a little further along than Preston’s.”

Even so, both sons want what’s best for their mother.

“Preston and Jayden do feel concerned about their mom at times. They’re aware of her struggles, both past and present, and they want the best for her and know that having a relationship with her will help matters,” the source continued.

On the family front, Britney and Jamie Lynn have been working on mending fences.

“[They] are doing better, and they are planning on getting together soon,” another source revealed. “The girls decided to keep their relationship problems out of the public eye. They FaceTime every few weeks, and Jamie Lynn is planning on visiting Britney next month in L.A.”

Britney has stayed closest to her brother, Bryan Spears, who moved into her home following her split from Sam Asghari in August 2023.

“[The two] are still close,” the insider shared. “He stays out of her issues with the rest of the family.”

And while she works on family ties, Britney hasn’t given up on her love life. On September 7, she revealed she went on a sushi date — but admitted it was “absolutely horrible.”