Kim Kardashian and Britney Spears’ Friendship Through the Years: From Partying Days to 2025 Reunion

Britney Spears and Kim Kardashian may be two of the most well-known women on the planet, but they also share a decades-long friendship.

The pair is generally understood to have met in the early aughts, when they were both known for partying and enjoying a Hollywood lifestyle.

More than a decade later, in November 2025, Kardashian and Spears reunited in a selfie that threatened to break the internet. In the pic, shared via Kardashian’s Instagram Story, the pair could be seen posing with Khloé Kardashian and the “Toxic” singer’s manager, Cade Hudson.

“Calabasas Nights,” Kim captioned the post at the time.

The snap showed the group basking in pink light while sitting in a bed and making silly faces for the camera. Kim was wearing a black robe with her hair pulled back, while Khloé wore Christmas pajamas and Spears was decked out in a yellow-and-white outfit. Hudson wore a Mickey Mouse tee with a dark hoodie.

The photo was also the first time Kim and Spears have been photographed since 2012, but the pair have a relationship that dates back many years. Keep scrolling to read more about Kim’s friendship with Spears.

Spears and Kim Met Through Paris Hilton

Both Spears and Kim have a mutual friend who connected them: media mogul Paris Hilton, who was friends with both women in the late 1990s and early 2000s.

Spears Once Said She and Kim Have Different Aesthetics

In October 2012, Spears compared her fashion style to her friend Kim’s, who famously got her start helping Hilton when the hotel heiress hired her as her wardrobe assistant.

“I love my jeans and my sweats. I’m really just a tomboy at heart,” the pop star told Elle Magazine at the time. “So it’s really hard for me to be like Kim Kardashian.”

She added that having “makeup and hair ready every time I go out of my house. I’m not a believer in that, you know? On the other hand, when you do wear those sweats, you’re like, ‘Oh God, I should step it up a notch.’”

Spears Defended Kim During Her First Pregnancy

Kim weathered a slew of negative comments about her body while pregnant with her oldest child, daughter North West, in June 2013 Spears came to her friend’s defense, while discussing how she also faced similar criticisms in the media while pregnant.

“I see Kim and what she went through when she was pregnant — the tabloids were so mean to her because she was big. At one point in the show she was upset and said something like, ‘I would be lying if I said that the criticism from the paparazzi while I’ve been pregnant hasn’t taken a toll on me.’ And I was like, ‘Bless her heart,’ because I remember that time,” she told InStyle in the magazine’s January 2014 issue, per UPI.

She continued: “First of all, you are already emotional, and then the paparazzi are taking pictures of you pregnant. That should be the time when your body is the most treasured. I loved being pregnant for so many reasons, not to mention the sex is awesome then.”

Kim Defended Spears Following the Singer’s 2021 Doc

Kim returned the favor in 2021, when she spoke out in support of Spears following the release of The New York Times documentary Framing Britney Spears.

“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,” Kim wrote via her Instagram Story, per ABC. “No matter how public someone’s life may seem, no one deserves to be treated with such cruelty or judgment for entertainment.”

Kim added that she could empathize with Spears’ plight. She recalled that after the birth of daughter North West, she “cried every single day … mainly from the pressures of being constantly compared to what society considered a healthy pregnant person should look like — as well as being compared to Shamu the Whale by the media.”

She continued: “I was shamed on a weekly basis with cover stories that made my insecurities so painful I couldn’t leave the house for months after. It really broke me” and ultimately concluded, “You just never fully know what someone is going through behind the scenes and I’ve learned through my own experiences that it’s always better to lead with kindness.”

Kim and Spears Reunite in 2025

The duo met back up on November 14 for a sleepover at Kim’s house. They were joined by Kim’s sister Khloé and Spears’ manager, Hudson. Kim shared a selfie of the group lounging in bed via her Instagram Story and captioned it simply, “Calabasas Nights.”