Britney Spears appeared to be living out the lyrics of her own song “Slumber Party” on Friday night, when she cozied up in bed with Kim Kardashian and Khloé Kardashian during what looked like an intimate late-night hangout in Hidden Hills. The two playful selfies, shared to Kim’s Instagram Stories, instantly sparked fan frenzy across social media (Page Six).

The “Toxic” singer, now 43, was joined by her longtime manager Cade Hudson as the group settled into Kim’s luxurious Calabasas-area home. “Calabasas nights,” Kim, 45, wrote over the first photo, striking her signature pout while Britney stuck out her tongue in a cheeky, carefree pose. The relaxed and playful vibe seemed worlds away from Spears’ often scrutinized public life (People Magazine).

A second image — this time snapped by Hudson — revealed the full group sitting shoulder-to-shoulder on the bed, illuminated by a large pink mood light in the background. Kim wore a sleek black robe with her hair pulled back into a bun, while Khloé, 41, opted for festive Christmas-themed pajamas and loose wavy hair. Spears sported a yellow-and-white outfit that fans described as “classic Britney cozy style” on X (formerly Twitter).

Representatives for the Kardashians and Spears did not immediately respond to media requests for comment (Rolling Stone).

Longstanding connection between Kim Kardashian and Britney Spears

While their spontaneous sleepover surprised many, the connection between Spears and Kim actually stretches back decades. The two moved in overlapping celebrity circles in the early 2000s, with both sharing a close friendship with Paris Hilton. The pair were last photographed together at Clive Davis’ annual pre-Grammy gala in 2012 (WireImage; E! News).

Kim has also publicly supported Spears during some of the most difficult chapters of the pop star’s life. After watching the 2021 documentary Framing Britney Spears, which explored the harsh media scrutiny and legal saga surrounding Spears, Kim wrote that she felt “empathy” for the singer. “The way the media played a big role in her life the way it did can be very traumatizing,” Kim said on Instagram at the time, adding that no one deserves to be treated “with such cruelty or judgment for entertainment” (BBC News).

Later that year, reports surfaced claiming Kim had privately reached out to Spears to offer support as the singer fought to end her 13-year conservatorship. According to Closer magazine, an insider claimed Kim told Britney she would help in “any way possible” after hearing her emotional court testimony. Spears allegedly asked Kim to connect directly with her attorney, Samuel Ingham, expressing gratitude for the reality star’s willingness to help (The Guardian).

Judge Brenda Penny ultimately terminated the conservatorship in November 2021, granting Spears full legal freedom for the first time since 2008 (AP News).

A friendship renewed?

The sleepover, complete with purple lighting, cozy blankets, and casual outfits, marked one of the first times in years that Spears has been seen privately socializing with major Hollywood figures. Fans quickly speculated online whether the gathering hinted at a strengthening friendship between the women — or even a possible collaboration in the future.

Both Spears and Kim have recently been in the public eye: Spears following the release of her bestselling memoir The Woman in Me, and Kim with the ongoing success of The Kardashians reality series and her global fashion brand SKIMS (New York Times).

Whether the evening was simply a nostalgic reunion or the start of something more, the images certainly captivated fans — a reminder that even in the ever-evolving landscape of celebrity culture, some star connections endure across decades.