Love is in the air for Kendall Jenner! The 24-year-old Keeping Up With the Kardashians star recently made her followers go “awww” with her strawberry emojis for Devin Brooker. But before her new rumored NBA player beau, there was another pro baller Ben Simmons. And although many say that their on-off relationship ran its course, is there a chance for Kendall and Ben to get back together? It’s time to trace the timeline of their sweet romance to see if the KUWTK sister will ever date the 23-year old “exclusively” again.
Kendal Jenner’s dating life has always been fodder for the rumor mills just like it is for the rest of the Kardashian-Jenner clan. Although the young model tries her best to keep her romantic alliances under wraps, it’s the pictures that do most of the talking. And not unlike her sisters who have an affinity for NBA stars, so does this KUWTK celeb. The speculations of Phoenix Suns guard Devin Booker being Kendall’s someone special are rife right now. The recent flirty messages were a follow up of the two taking a road trip to Sedona in April and a mysterious Van Nuys Airport pickup in May. But with Kendall not making things with official yet, could it have something to do with Devin’s predecessor and fellow NBA athlete Benjamin “Ben” Simmons?
Originally from Australia, Ben Simmons is one of America’s rising basketball star players. A member of the Philadelphia 76ers, Ben met the KUWTK model via mutual friends sometime around June 2018. Page Six reported that the young pair was spotted on a lunch date and right after, a shopping trip together in Beverly Hills followed for Kendall and her basketball player. The link-up did raise a few eyebrows back then as it was just days ago that Kendall was captured during quite a heavy make-out session with Gigi and Bella Hadid’s brother Anwar at an after-party in NYC. But sources claimed it was Kendall “just having some fun” as by July 2018, Kendall and Ben’s relationship status was confusingly described as “dating and exclusive, though not ‘official.'” A day later, eagle-eyed fans caught Kendall snuggling up to Ben Simmons during Khloe Kardashian's Fourth of July pool party in Southen California. The pair was instantly dubbed an “item” before they were photographed yet again as they celebrated Ben’s 22nd birthday. August 2018 saw the couple vacationing with Khloe and baby daddy Tristan Thompson at a resort in Puerto Vallarta, Mexico. However, this apparently wasn’t the first time the couples were double dating as Kendall and Ben had earlier accompanied her sister to Dave Chappelle's family and friends-only private show at the Peppermint Club. But tragedy struck when September arrived and Kendall and Ben seemed to become history as the KUWTK star was spotted kissing Anwar Hadid again.
According to TMZ rumors were reignited for a round 2 when Kendall showed up at Ben's game at Wells Fargo Center in November. Kendall boo-ed Tristan at another game and sister Khloe defended her on Twitter by referring to Ben as “HER man.” Come December, the Keeping Up with the Kardashians regular was seen bonding with the NBA player’s mother Julie Simmons in Philadelphia as the Philadelphia 76ers, took on the Washington Wizards. The couple displayed tons of PDA at Drake’s New Year’s Eve party even amidst people talking about his rumored beef with Kendall’s brother in law Kanye West. January 2019 saw Ben feeding the fire of their link-up with some not-so-subtle Instagram flirting. "I do my own stunts," Kendall captioned her bikini photo with to which Ben replied with a "Come here .." comment. By late January, Kendall again enjoyed her NBA superstar’s mom’s company a second time in Philadelphia. Valentines Day 2019 had the couple step out for a dinner date at Zuma in New York City, but by May, Kendall spoke about her “uncertain” relationship with Ben to Vogue Australia while confessing, “I don’t want to bring too much attention to something if you don’t really know long term.” Kendall was very much single by the end of May as the two were reportedly, “on a break.” But right when KUWTK fans thought that Kendall and Ben had gone their separate ways, she was spotted yet again, at his basketball game in December 2019. The couple brought in the New Year together for a second time when the 76ers star rented out rooftop restaurant Attico in downtown Philadelphia. In February this year, the two attended Super Bowl 2020 at Had Rock Stadium in Miami following a low-key lunch date at New York City’s Bubby’s in January. Since then, Kendall and Ben seemed to have opted for a much more casual, “no-strings-attached” relationship owing to their busy schedules, as per US Weekly.
Now, with tittle-tattle of the Keeping Up with the Kardashians celeb getting close to new beau Devin Booker doing the rounds, and with the Instagram comments to prove them, Kendall and Ben seem to be over in all likeliness. But since Kendall is never one to squash or accept gossip related to her personal life, the rumor mills can be expected to keep on running.
Source: Page Six, TMZ, Vogue Australia, Us Weekly
