Selena Gomez has a lengthy history with several members of the Kardashian-Jenner family — and their overlapping inner circles.
The “Lose You to Love Me” singer started publicly hanging out with Kendall Jenner and Kylie Jenner in 2014 after the sisters were fans of Gomez. The friendship came amid the height of the Wizards of Waverly Place star’s on-again, off-again relationship with Justin Bieber. (Gomez and Bieber were first linked in 2011 but broke up over the years for different lengths of time before calling it quits for good in spring 2018.)
After sharing several snaps from Coachella together in April 2014, Gomez made headlines for unfollowing Kendall and Kylie weeks after the music festival. Sources told Us Weekly at the time that things got “messy” when Gomez felt “the Jenner girls were flirting with Justin and his crew.”
Amid various reports about the drama — including some claims that Gomez thought Kendall and Kylie weren’t good influences — Khloé Kardashian appeared to enter the chat, tweeting: “You want to play in the 20 year old pool …. Well I’m still in my 20s & I’m better at this game than you. Don’t f—k with my little sisters!”
The drama later settled. “Selena has no issues with the Jenner girls. They had an issue but they have cleared it up,” another source said at the time. “She has always liked the Jenner girls.”
In the years that followed, the Kardashians stars were rarely seen with Gomez and both Kendall and Kylie’s oldest sister, Kourtney Kardashian, and their close friend Hailey Bieber (née Baldwin) were linked to Justin during his off periods with the Only Murders in the Building star.
The “Peaches” crooner and the actress got back together in late 2017. Two months after they split again in May 2018, Justin and Hailey (who has consistently stayed close to Kendall and Kylie) got engaged. They wed in September 2018 and fans continued to read into Hailey’s various social media posts, assuming she was shading Gomez over the years.
“I was never with him when he was in a relationship with anybody. That’s the end of it,” Hailey said during an appearance on the “Call Her Daddy” podcast in September 2022, addressing the accusations of overlap for the first time. “That was a situation where I know for a fact that it was the right thing for them to close that door.”
Gomez’s connections with the family don’t stop with Kendall, Kylie, Hailey or Justin, however. In 2016, Gomez stepped in when her longtime bestie Taylor Swift had drama with Kim Kardashian and then-husband Kanye West. Gomez spoke out when the Selfish author leaked footage of the rapper’s conversation with Swift about using her name in his song “Famous.”
Three years later, Gomez declared she was on the “Midnight” singer’s “side for life” when she posted and deleted a pic supporting Kim’s brand Skims.
Things came full circle in February 2023 when Gomez found herself commenting on several videos about the past drama — including one clip of Hailey shading Swift — via TikTok. The social media scandal, which resulted in Gomez taking a step back from the app, was sparked when Kylie and Hailey were accused of mocking the Rare Beauty founder’s eyebrows, which the Life of Kylie alum denied.
Scroll through for a complete timeline of Gomez’s ties to the Kardashian-Jenner family:
Credit: Frank Micelotta/Shutterstock
June 2009
Khloé showed Gomez some love before she started spending time with the famous family. “Who thinks @selenagomez is the prettiest, sweetest girl?” she tweeted in June 2009. “I might be obsessed with her! LOL I’m serious. My little sisters love her!”
Credit: Courtesy of Kylie Jenner/Instagram
April 2014
Gomez hit Coachella with the Jenner sisters. “MY FAVORITE PEOPLE 🌼🌺🌸,” Kylie captioned a group snap.
Credit: Shutterstock (2)
April 2014
After the musical festival, the Disney alum turned heads when she unfollowed Kendall and Kylie via Instagram. “Selena said the Jenner girls were flirting with Justin and his crew. She was pissed and overreacted,” an insider told Us at the time.
Credit: Courtesy of Kris Jenner/Instagram
October 2014
Gomez shared a private plane with Kris Jenner after a trip to Paris.
Credit: Courtesy of Poppy Jamie/Instagram
November 2014
The “Dance Again” songstress was present at Kendall’s 19th birthday alongside Cara Delevingne.
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May 2015
Gomez appeared to look emotional as she chatted with and hugged Kris on the Met Gala red carpet.
Credit: Shutterstock (2)
November 2015
Insiders told Us that Justin and Kourtney had a fling following another one of his splits from Gomez. By the end of the year, the “Sorry” singer’s initial three-month romance with Hailey began.
Credit: Chelsea Lauren/Shutterstock
July 2016
Gomez made it clear she wasn’t impressed with Kim when she dropped the videos of West’s conversation with Swift.
“There are more important things to talk about. Why can’t people use their voice for something that f—king matters?” she tweeted at the time. “Truth is last thing we need right now is hate, in any form. … This industry is so disappointing yet the most influential smh.”
Credit: Shutterstock (2)
May 2018
Kylie and Gomez reunited at the Met Gala, posing for a photo together.
Credit: Courtesy of Selena Gomez/Instagram
October 2019
Gomez shared a pic wearing a black piece from Kim’s Skims line. “Legit So freaking comfortable @skims,” she wrote via Instagram Stories.
Hours later, she deleted the post and uploaded a pic with Swift.
“My ride or die I would die for this one,” Gomez captioned the selfie. “Thank you for forever being by my side. You have taught me so much, walked through all of this with me, STAYED and you remind me to be a better, human being. I’m on your side for life.”
Credit: Courtesy of Kendall Jenner/Instagram; YouTube
April 2021
Eagle-eyed fans noticed Kendall sported the pink Rodarte dress that Gomez wore in her “De Una Vez” music video earlier that year.
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February 2023
Gomez reacted to a TikTok video theorizing that Hailey and Kendall had subtly poked fun at her via a video lip-syncing to audio trend, “And I’m not saying she deserved it, but I’m saying God’s timing is always right.”
“I don’t let these things get me down!” Gomez responded to a fan theory calling the since-deleted video shady. “Be nice to everyone!”
Credit: Shutterstock (3)
February 2023
Kylie denied that she and Hailey were throwing shade at Gomez on social media after the three women shared posts about eyebrows around the same time.
“This is reaching. no shade towards selena ever and i didn’t see her eyebrow posts!” the reality star wrote via TikTok. “U guys are making something out of nothing. this is silly.”
Gomez responded at the time: “Agreed @kyliejenner it’s all unnecessary. I’m a fan of Kylie!”
Credit: Courtesy of kimandnorth/TikTok
February 2023
While Gomez announced she planned to step back from social media after the drama in the comments section, her little sister, Gracie, took to the app with Kim’s eldest daughter, North, to make “homemade pasta.” The two girls previously posted videos of their sleepover with Kourtney’s daughter, Penelope, in November 2022.
Credit: Francis Specker/CBS
January 2024
Gomez made headlines during the 2024 Golden Globes when she appeared to shade Kylie during an apparent gossip session with Taylor Swift and Keleigh Teller. Fans claimed to read their lips and speculated that the trio were discussing Kylie’s relationship with Timothée Chalamet. However, a source told Us Weekly that there was “never any drama” between Gomez and Kylie at the awards ceremony.
