Their previous relationships
After 2 years, Styles ended the relationship with Olivia Wilde. The two met on the set of the psychological thriller, Don’t Worry Darling. Jenner, who was dating NBA star Devin Booker has broken up for the second time. The two were also dating for 2 years.
Where the speculation started
Although there has been radio silence from both the supermodel and the singer, Twitter detectives have been hard at work piecing together the puzzle.
Jenner recently attended Harry Styles’ concert, and fans began speculating whether this was a love of his music or another matter of the heart. Video footage captured the model dancing alongside her longtime friend Hailey Bieber and sister Kylie Jenner, and one viral TikTok even alleged that the singer blew a kiss to Jenner during his song “Love of My Life” (which many believe is about her).
@jennas.house Hailey is kinda blocking her in the video but caught me so off guard #harrystyles #hslot #loveontour #kendalljenner ♬ original sound – jenna
The two have been romantically involved on multiple occasions from 2013 -2019 but found dating to be challenging and decided to end the relationship in 2019.
Through their break-ups, it appears that they have been learning on each other to process the splits, proving that even after their relationship with each other ended, they maintained friendship.
An inside source told The Sun: “Harry and Kendall have always stayed in touch, but in light of their recent splits, they have more time for one another.”
The source adds, “Close as they are, Harry and Kendall found dating difficult, and all of those practical problems they faced years ago are still there,” the source continued. “That said, their friends speculate that they might hang out over the holidays. In the past they have gone away together shortly after respective break-ups, so they could very well end up on a yacht soaking up the sun in the next couple of months.”
In 2019, Jenner even made a guest appearance on The Late Late Show when Styles filled in for host James Corden.
We have our eyes glued to see if this blossoms into a beautiful relationship again.
Featured Image: @kendaljenner/Instagram and @harrystyles/Instagram