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Selena Gomez vs the Kardashian-Jenners: A Veritable Rollercoaster of Highs and Lows

2014 marked a shift in Selena Gomez’s social circle. The singer began appearing publicly with Kendall and Kylie Jenner, who were previously fans of Selena’s work. This newfound friendship blossomed during a tumultuous period for Gomez—the height of her on-again, off-again relationship with Justin Bieber. (Their romance ignited in 2011, endured multiple breakups throughout the years, and finally ended, presumably forever, in the spring of 2018.) Whether seeking new connections or a distraction from the rollercoaster relationship, Selena found herself surrounded by the Jenner sisters, a dynamic that would play out in the public eye for years to come.

Scroll through for a complete timeline of Selena Gomez’s ties to the Kardashian-Jenner family in all its dramatic glory:

June 2009

Back in June 2009, Khloe Kardashian wasn’t shy about her admiration for the rising Disney star. A tweet gushed about Selena, calling her “the prettiest, sweetest girl,” even admitting a playful obsession. The mention of her “little sisters loving her” suggests a wholesome connection, perhaps built on shared experiences in the entertainment industry or through mutual friends.