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Kim Kardashian and Britney Spears Cozy Up With Khloe at Pajama Party: ‘Calabasas Nights’

By Eric November 16, 2025

On November 14, 2023, pop icon Britney Spears and reality star Kim Kardashian delighted fans with a cozy pajama party, showcasing their friendship and a fun-filled night in a series of Instagram posts. The gathering, which also included Khloé Kardashian and Spears’ longtime manager Cade Hudson, was a heartwarming display of camaraderie. Kim shared a snapshot of the group lounging on a bed, with Spears playfully sticking out her tongue and flashing a peace sign while wearing a vibrant yellow off-the-shoulder top. Khloé, dressed in festive holiday-themed pajamas, added a cheeky smile to the mix, creating an atmosphere of warmth and joy. The caption for the post, “Calabasas Nights,” set the tone for a relaxed evening among friends.

The following day, Britney shared a delightful video of herself nestled between Kim and Khloé, where they shared giggles and affectionate kisses. The playful banter continued as Khloé humorously referred to their lounging arrangement as a “geriatric bed,” while Britney expressed her surprise at the vibrating mattress, exclaiming, “What the f—k!” The video also featured Khloé’s daughter True and Kim’s daughter Chicago showing off their dance moves, further highlighting the family-friendly nature of the gathering. Britney expressed her gratitude in the caption, writing, “Such a warm, beautiful, kind family… Thank you for allowing me to play with your kids and dinner!!! It was an honor to spend time with you guys!! Happy Holidays.” This heartfelt sentiment underscores the supportive environment that both women have fostered, especially in the wake of Britney’s recent challenges.

The friendship between Britney Spears and Kim Kardashian dates back to the early 2000s, a time when both women were navigating the complexities of fame. Kim previously expressed her empathy for Britney in response to the 2021 documentary “Framing Britney Spears,” which shed light on the intense media scrutiny that Spears faced throughout her career. Kim noted the trauma that such treatment can inflict, emphasizing that no one deserves to be subjected to cruelty for entertainment. Recently, Spears has been in the headlines due to the release of her ex-husband Kevin Federline’s memoir, which contains sensational claims about their marriage. After a brief hiatus from Instagram, she returned to share her thoughts on the tumultuous year, hinting at the importance of self-care and boundaries. This pajama party not only highlights their enduring friendship but also serves as a reminder of the strength and resilience found in supportive relationships, especially during challenging times.

Britney Spears
and
Kim Kardashian
reunited for what appeared to be an epic pajama party.

On Friday (Nov. 14), the Skims mogul shared a glimpse of the group getting cozy on a bed with Khloé Kardashian, along with the pop star’s longtime manager, Cade Hudson.

Related

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Britney Spears Vows to ‘Bring Substance to the Table’ in Post About Pushing Back Against ‘Garbage’ Comments About Her

“Calabasas Nights,” Kim captioned the first snapshot on her
Instagram Story
.

In the image, Spears sticks out her tongue while Kim puckers her lips and flashes a peace sign, with Khloé and Hudson looking on. The “Toxic” singer wore a yellow off-the-shoulder top, while Kim sported a dark hooded jacket.

A
second photo
shows the quartet playfully posing under dark pink lighting, as Khloé dons festive holiday-themed PJs and flashes a cheeky smile.

The next day, Spears shared a video of herself nestled between Kim and Khloé, planting a kiss on each of their cheeks as the trio giggled.

“Oh, we’re just chilling,” Britney says in the
Instagram
clip, prompting Khloé to joke that they’re lounging in their “geriatric bed.” The “Slumber Party” singer then reveals that the mattress vibrates, before panning the camera to the edge of the bed and shouting, “What the f—k! What the f—k!”

The brief video also showed Khloé’s daughter True and Kim’s daughter Chicago performing a little dance for her.

She captioned the post, “Such a warm, beautiful, kind family… Thank you for allowing me to play with your kids and dinner!!! It was an honor to spend time with you guys!! Happy Holidays.”

View this post on Instagram

Britney and Kim’s friendship dates back to the early 2000s. In 2021, the
Keeping Up With the Kardashians
star
reacted to the
Framing Britney Spears
documentary, which exposed the misogynistic media scrutiny Spears endured for years.

“So I finally watched the Britney Spears documentary this week and it made me feel a lot of empathy for her,” Kim wrote on Instagram at the time. “The way the media played a big role in her life the way it did can be very traumatizing and it can really break even the strongest person. No matter how public someone’s life may seem, no one deserves to be treated with such cruelty or judgement for entertainment.”

In recent weeks, Spears has made headlines after
deactivating
and then
reactivating her Instagram
amid drama surrounding the release of her ex-husband Kevin Federline’s tell-all memoir,
You Thought You Knew
, which contains several sensational claims about their two-year marriage.

“So much has happened this year, it’s crazy …,” Spears wrote on IG in early November after reactivating her account. “I try to live within my means and the book, ‘Draw the Circle’ is an incredible perspective. Get your ballerina 🩰, circle, and own your boundaries.”

She added, “It’s incredibly strict and somewhat of a form of prayer but with so many endless possibilities in life, it’s important to do you and keep it simple. I know there is a confusing side too. The devil is in the details but we can get to that later 😳😂🤧.”

Check out Kim’s selfies
here
and
here
on her Instagram Story.

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