When it comes to public appearances, Britney Spears’ sons Preston, 19, and Jayden, 18, are notoriously private. However, they just made a joint appearance for a family reason, and the rare new photo shows how much they’ve grown up!
The boys, who Britney shares with ex Kevin Federline, attended their 17-year-old cousin Maddie’s senior night for her high school softball team. Maddie, Jamie Lynn Spears’ daughter, shared photos from the special game on Wednesday.
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It included a snap of Maddie standing in between her two cousins, with her little sister Ivey, 7, in the picture as well. The teens were both dressed in dark blue, baggy jeans and t-shirts for the game. (Jamie Lynn shared the same photo and others of her daughter’s senior night on Instagram too.)
It’s so cool to see these cousins reunited, and it makes us believe there might be some healing in the Spears’ family rift.
After the “Toxic” singer’s 13-year conservatorship was ended by a judge in 2021, Britney was estranged from her sons, who moved to Hawaii with their father. She reunited with her son Jayden in Dec. 2024, nearly three years after last seeing him. “He came back and he feels older and smarter than me !!!” Spears wrote. She added, “He’s a man and I cry everyday of my life because of the miracle and genius he is !!!” she wrote on Instagram at the time.
In August 2025, Britney reflected again on being estranged from her kids. “We’re just people so fragile and human,” she wrote on Instagram, per Us Weekly. “The hardest years of my life were my two sons gone for those 3 years … I was cut off from calling or texting and I remember in shock my secret to survival was denial and a lot of tears.”
Britney was also estranged from her sister Jamie Lynn after the Zoey 101 star released her memoir, Things I Should Have Said. However, a source recently told Us Weekly, “Britney and Jamie Lynn are doing better, and they’re planning on getting together soon. 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.”
Another source added, “They really love one another, but they can be hardheaded siblings.”
It’s unclear if Britney attended Maddie’s senior night, but the fact that her sons were there showed some healing in these relationships. And we could’t be happier for Britney!
Before you go, check out Britney Spears’ best quotes about motherhood.
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