See Britney Spears’ Sons in Rare Pic With Jamie Lynn Spears’ Daughter

Britney Spears’ sons Sean Preston and Jayden James, whom she shares with ex Kevin Federline, reunited with their cousin—Jamie Lynn Spears’ daughter Maddie—in a rare appearance at her baseball game.

Britney Spears’ sons wanna scream and shout for one of their own.

The “Gimme More” singer’s kids Sean Preston, 20, and Jayden James, 19—whom she shares with ex-husband Kevin Federline—made a rare appearance to cheer on their cousin Maddie Watson, 17, as she competed in a high school baseball game.

In a photo shared on Instagram Sept. 17, Maddie—whose mom is Britney’s sister Jamie Lynn Spears and dad is Casey Aldridge—posed in her athletic gear with her right arm in a black sling. She was joined by Britney’s sons as well as her sister Ivey Watson, 7, whom Jamie Lynn shares with husband Jamie Watson.

For the leisurely outing, Sean kept it casual in a fitted white T-shirt and baggy dark wash jeans with a pair of headphones around his neck. Jayden opted for a similarly laidback style, sporting an oversized beige top and dark denim.

While Britney, 43, has had a complex dynamic with her sister—which she described in her 2023 memoir The Woman in Me—she and Jayden reunited last December after a lengthy estrangement.

“I hadn’t seen him in 2 and half years or maybe 3,” she wrote on Instagram at the time alongside three photos of her youngest son. “I’m in shock !!!”

In fact, the pop star couldn’t help but gush about how much Jayden had developed during their time apart.

“He came back and he feels older and smarter than me !!!” she continued. “He’s a man and I cry everyday of my life because of the miracle and genius he is !!!”

Since then, the mother-son duo appear to have continued working on their relationship. In June, Britney shared a clip of Jayden behind the wheel of her convertible in a since-deleted Instagram post, followed by a mirror selfie of the two a few days later.

The Grammy winner has also praised her son’s musical abilities, offering her fans a glimpse of his piano skills in March. Alongside the Instagram video, which she later took down, she simply wrote, “WOW WOW WOW!!!”

Keep scrolling to see more of Britney with her boys…

“It’s so crazy how time flies …. My boys are so big now!!!!” Britney wrote in a March 2021 Instagram post. “I know … I know … it’s very hard for any mama especially a mama with boys seeing them grow up so fast !!!! Talk about enough to make you go to your knees … GEEZ  !!!! I’m extremely lucky because my two babies are such gentleman and so kind that I must have done something right !!!! I haven’t posted pictures of them for some time cause they’re at the age where they want to express their own identities and I totally get it.”

“Great time at Disneyland today …. but I don’t remember ever getting that wet on splash mountain!!!” the “Stronger” star captioned an August 2019 Instagram photo series. “Geeez …. anyhow my boys are older now, so they don’t like their picture taken ever… so I was thrilled today when they said SURE!!!!! Such a great place!!!!!”

Spears shared a video of arts and crafts time with her sons in 2018.

“Getting silly with my kids on our day off from tour!” the artist captioed the 2018 post.

“This was from our lil trip to see Aladdin,” Spears captioned the 2018 photo. “What a great show!!!!”

 

“Love when we go to our favorite spot on Sundays,” she wrote on Instagram in 2018. “The boys are bigger than me now!!!!!”

The family enjoyed a trip to London during Spears’ Piece of Me Tour. 

The boys and their mom did a little surfing during their 2017 trip to Hawaii.

“Going for a walk with my son and the dog always does wonders for my mood…” she wrote in 2017.

The dynamic duo saw some aquatic creatures in Las Vegas in 2016.

Spears and her boys celebrated Thanksgiving with their family members, including her sister Jamie Lynn Spears.

“Happy gobble gobble!” the Grammy winner writes in 2015.

The “Oops…I Did It Again” star celebrated July 4, 2015 at the Happiest Place on Earth. 

The “Toxic” singer shared a picture of her enjoying “the mermaid life” in 2015.

Spears’ boys are all grown up.

The artist’s sons helped her hold up her surfboard at the 2015 Teen Choice Awards.

The terrific trio shared a sweet smile in this 2015 pic.

Look at these cuties!

The singer and her two boys went all out for Halloween 2014.

“I’ve got the two cutest boys in the world!” she captioned the 2013 pic. “I hope y’all are having as nice of a #mothersday as I am!”

The proud mama took her boys to see the Los Angeles premiere of Smurfs 2 in 2013.

The boys enjoyed a sweet treat with their mom at this 2013 game between the Los Angeles Dodgers and the San Diego Padres.

The singer took her sons to the Broadway production of The Lion King in 2011.