Selena Gomez's Rollercoaster Relationship with the Kardashian-Jenners
Selena Gomez's rollercoaster relationship with the Kardashian-Jenners: From fleeting friendships to defending Taylor Swift during a feud with Kim Kardashian Discover the timeline of their ups and downs
Selena Gomez has a longstanding connection with multiple members of the Kardashian-Jenner family and their interconnected social circles.
The singer of "Lose You to Love Me" began being seen in public with Kendall and Kylie Jenner in 2014 after the sisters became fans of Gomez. This friendship blossomed during the peak of Gomez's on-again, off-again romance with Justin Bieber. (Gomez and Bieber were first rumored to be dating in 2011 but experienced multiple breakups before finally ending things for good in the spring of 2018.)
After posting several photos together at Coachella in April 2014, Gomez made headlines for unfollowing Kendall and Kylie a few weeks later. Sources revealed that Gomez felt the Jenner girls were getting too close to Justin and his friends, causing tension. Amid the drama, Khloé Kardashian weighed in with a tweet that seemed to defend her younger sisters, warning Gomez not to mess with them.
The drama eventually calmed down. According to another source at the time, "Selena has no problems with the Jenner girls. They had a conflict, but they've resolved it. She has always been fond of the Jenner girls."
In the years that passed, the Kardashians stars were seldom seen with Gomez. Both Kendall and Kylie's older sister, Kourtney Kardashian, and their close friend Hailey Bieber (formerly Baldwin), were associated with Justin during his breaks from the Only Murders in the Building actress.
After getting back together in late 2017, the "Peaches" singer and the actress split again in May 2018. Two months later, Justin and Hailey (who has remained close with Kendall and Kylie) got engaged, and were married in September 2018. Over the years, there were assumptions from fans that Hailey was indirectly criticizing Gomez in her various social media posts.
However, during an appearance on the "Call Her Daddy" podcast in September 2022, Hailey addressed the accusations for the first time, stating, "I was never with him when he was in a relationship with anybody. That's the end of it. That was a situation where I know for a fact that it was the right thing for them to close that door."
Gomez's ties to the family extend beyond Kendall, Kylie, Hailey, and Justin. In 2016, she defended her longtime friend Taylor Swift when she ran into trouble with Kim Kardashian and her husband Kanye West. Gomez spoke out when Kardashian leaked footage of West's conversation with Swift about using her name in his song "Famous."
Three years later, Gomez reaffirmed her loyalty to the singer by declaring herself on Swift's "side for life" when she posted and then deleted a picture showing support for Kim's brand Skims.
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In February 2023, Gomez found herself engaging in commentary on various videos depicting past drama, including one where Hailey shaded Swift, on TikTok. This social media scandal led to Gomez distancing herself from the app, sparked by allegations that Kylie and Hailey had made fun of Gomez's eyebrows, which the Life of Kylie star denied. For a detailed timeline of Gomez's connections to the Kardashian-Jenner family, continue scrolling.
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Selena Gomez’s Ups and Downs With the Kardashian-Jenners
Selena Gomez has a lengthy history with several members of the Kardashian-Jenner family — and their overlapping inner circles.
Singer "Lose You to Love Me" began publicly hanging out with Kendall Jenner and Kylie Jenner in 2014 after they became fans of hers. Their friendship started during the height of her on-again, off-again relationship with Justin Bieber. After sharing photos together at Coachella in April 2014, Gomez made headlines by unfollowing Kendall and Kylie a few weeks later, with sources reporting that it was because she felt they were flirting with Justin and his crew.
Amidst swirling drama rumors, including speculation that Gomez disapproved of Kendall and Kylie's influence, Khloé Kardashian chimed in, 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 mess with my little sisters!"
The drama eventually subsided. "Selena has no problems with the Jenner girls. They had a disagreement but they've resolved it," another source stated at the time. "She has always been fond of the Jenner girls."
After this, the Kardashians stars were rarely seen with Gomez, and both Kendall and Kylie’s oldest sister, Kourtney Kardashian, and their close friend Hailey Bieber (formerly Baldwin) were linked to Justin during his off periods with the Only Murders in the Building star.
In late 2017, the singer and the actress got back together. Two months after they split again in May 2018, Justin and Hailey (who has consistently stayed close to Kendall and Kylie) got engaged. They married in September 2018 and fans continued to analyze Hailey’s various social media posts, assuming she was throwing shade at Gomez over the years.
During an episode of the "Call Her Daddy" podcast in September 2022, Hailey addressed the accusations of overlap for the first time. She stated, "I was never with him when he was in a relationship with anybody. That’s the end of it. That was a situation where I know for a fact that it was the right thing for them to close that door."
However, Gomez's connections don't stop with Kendall, Kylie, Hailey, or Justin. In 2016, Gomez supported her longtime bestie Taylor Swift during the drama with Kim Kardashian and Kanye West. She spoke out when the footage of the rapper’s conversation with Swift about using her name in his song "Famous" was leaked by the author of "Selfish."
Three years later, Gomez announced her unwavering support for the "Midnight" singer, stating she was on her side for life when she posted and then deleted a picture endorsing Kim's brand Skims.
In February 2023, Gomez found herself engaging in various TikTok comments about past drama, including a video in which Hailey appeared to criticize Swift. The social media scandal prompted Gomez to take a break from the app and was ignited by accusations that Kylie and Hailey had ridiculed the founder of Rare Beauty's eyebrows, which the Life of Kylie star denied.
Scroll through for a complete timeline of Gomez’s ties to the Kardashian-Jenner family:
Credit: Frank Micelotta/Shutterstock
June 2009
Khloé expressed her admiration for Gomez before she began hanging out with the well-known 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.
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April 2014
After the music festival, the former Disney star grabbed attention by unfollowing Kendall and Kylie on Instagram. According to an insider who spoke to Us at the time, "Selena claimed that the Jenner sisters were flirting with Justin and his group. She was angry and reacted strongly.”
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.
Credit: Shutterstock (2)
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
Us sources revealed that Justin and Kourtney had a brief relationship after he broke up with Gomez. Later that year, Justin started a three-month romance with Hailey.
Credit: Chelsea Lauren/Shutterstock
July 2016
Gomez expressed her disappointment in Kim when she released the videos of West's conversation with Swift. "There are more pressing issues to address. Why can't people speak out about something that truly matters?" she tweeted. "The last thing we need right now is more hate, in any form. This industry is incredibly disheartening yet also the most influential, shaking my head."
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.
She removed the post hours later and shared a photo with Swift.
In the caption of the selfie, Gomez wrote, "My loyal friend, I would do anything for this one. Thank you for always being there for me. You have taught me a lot, been with me through it all, and stuck around, reminding me to be a better person. I will always be on your side."
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 responded to a TikTok video speculating that Hailey and Kendall had indirectly teased her by participating in a video lip-syncing to the 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 throwing shade at Gomez on social media with Hailey, after the three women shared posts about eyebrows around the same time. She wrote on TikTok, “This is reaching. no shade towards Selena ever and I didn’t see her eyebrow posts! 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
After the controversy in the comments section, Gomez stated her intention to take a break from social media. Meanwhile, her younger sister Gracie and Kim’s eldest daughter, North, teamed up on the app to share their experience making “homemade pasta.” In a previous post, the two girls had shared videos of their sleepover with Kourtney’s daughter, Penelope, in November 2022.
Credit: Francis Specker/CBS
January 2024
During the 2024 Golden Globes, Gomez sparked controversy when she was seen apparently gossiping with Taylor Swift and Keleigh Teller, leading fans to speculate that they were discussing Kylie's relationship with Timothée Chalamet. However, a source informed We that there was no actual drama between Gomez and Kylie at the awards ceremony.
