Britney Spears was once incredibly close to Jamie Lynn Spears’ daughter, Maddie Aldridge. Their special bond began on Maddie’s first day in this world, in 2008, as Britney carved time out of her busy schedule to fly to Mississippi and meet her in person. The gesture was made even sweeter by the fact that the two sisters weren’t close throughout Jamie Lynn’s pregnancy. In the “Toxic” hitmaker’s bombshell memoir, “The Woman In Me,” Britney revealed that she only learned she was expecting in the press because her loved ones kept the pop star in the dark.

Meanwhile, in Jamie Lynn’s own memoir “Things I Should I Have Said,” she asserted, “To this day, the hurt of not being able to tell my sister myself lingers.” The former child star later shared her perspective on the situation at the time, acknowledging, “[My team] went so far as hiding my pregnancy from my sister, claiming, ‘It’s too risky to tell Britney about the baby.’ I needed her more than ever, and she wasn’t able to help me in my most vulnerable time,” (via Us Weekly).

Britney more than made up for the lost time by solidifying her bond with her niece through the years. In 2015, paps caught the “Perfume” songstress carrying her niece while her son walked closely behind (via YouTube). In 2018, Jamie Lynn shared a sweet photo on Instagram showcasing how her entire family, including Britney and her kids, showed up to celebrate Maddie’s birthday. Another video from the happy day sees the family singing “Happy Birthday” to the 10-year-old.

Britney Spears couldn’t bear the thought of losing Maddie Aldridge

In February 2017, 9-year-old Maddie Aldrige nearly lost her life when the ATV she was riding on flipped into a pond. In a series of since-deleted tweets posted to X, formerly known as Twitter, in 2022, Britney Spears recalled that her mom, Lynne Spears, was the one who informed her about the accident. However, in all her understandable confusion and grief, Lynne failed to mention that doctors were trying to revive Maddie, leaving the pop star to think that she had passed away.

Thus, after the call ended, she “started throwing things,” (via Page Six), confessing, “My mind was completely and absolutely gone […] I lost my mind at that moment.” Then, the “…Baby One More Time” singer wept until she was finally reassured that there was actually still hope for her niece’s survival. Elsewhere in 2017, Britney took to X to request her fans keep Maddie in their prayers. As her niece’s condition improved she thanked everybody for their well wishes. The iconic pop star celebrated Maddie’s recovery in style by taking her and her sons out on a special day to Planet Hollywood in March.

Two years later, Jamie Lynn took to Instagram to share that she and her big sis had bought all of their children together for a fun vacation. The since-deleted video showed the kids curiously watching fish at the aquarium, go-karting, and enjoying some fast food. In 2019, the reality TV star posted a candid pic of her two young daughters lying on the floor with their aunt to further cement their closeness.

Britney Spears and Maddie Aldridge sadly don’t seem close anymore

Britney Spears and Jamie Lynn Spears’ feud had a heartbreaking effect on Maddie Aldridge. While speaking to Variety in 2023, the “Zoey 101” alum divulged that her family drama had thrust her into the spotlight against her will and gravely affected her wellbeing. When the interviewer asked how she spoke about Britney to Maddie, Jamie Lynn answered: “I say, “‘You should be so proud. Look at what your family’s done and accomplished.'”

The former Nick star also noted that she explained that their family would always be a hot topic, but encouraged Maddie to see things in a different light. Jamie Lynn recalled her sweet words: “‘Look at what an example of a strong female you have. You have something to be proud of, and you should have pride in that.'” The feud naturally seems to have impacted Maddie and Britney’s relationship since the duo hasn’t been spotted together in years. It’s worth noting that their bond seemingly survived the early days of the drama, though.

While Britney publicly made some of her shadiest jabs at Jamie Lynn in 2021, she privately treated her nieces to a care package consisting of adorable stuffed toys and a fancy purse. Interestingly, fans believed that Britney’s gifts were actually a message to them. The “Womanizer” hitmaker reportedly remained close to Maddie throughout her conservatorship battle (unlike Jamie Lynn). In April 2021, a source told E! News that Britney consistently checked in with her nieces because she took great interest in all the little developments in their lives.