Jenner and Simmons’ Up and Down Relationship: A Timeline

– Jenner and Simmons had an on-and-off relationship for two years.
– They took breaks due to their careers and distance.
– The couple likely broke up in early 2020 before Jenner began dating Devin Booker.

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Kendall Jenner’s on-again, off-again relationship with Ben Simmons has been nothing short of a rollercoaster. The couple, who began dating in 2018, has taken multiple breaks during their two-year relationship. Almost a year into dating, the duo went on their first break, as reported by E! News. However, the split was short-lived, as Jenner confirmed her relationship with the 76ers basketball player during an appearance on “The Ellen DeGeneres Show.”

Nevertheless, the couple decided to hit the pause button again in May 2019, just after Jenner spoke highly of Simmons during an interview with Australian Vogue. In the interview, Jenner stated that she could envision herself getting married to Simmons someday. But, as fate would have it, the couple went their separate ways. Despite the many pauses in their relationship, the couple rekindled the romance just in time for the 2019 holiday season, as reported by People.

“They’ve been on and off, and there are periods where they definitely lost touch, but they’ve always had their eye on one another,” said an anonymous source to People. Adding further, “Their breakup always seemed more like a break because of careers and distance.” However, the couple likely called it quits in early 2020, right before Jenner started seeing Devin Booker.

The reality TV star has been romantically linked with multiple celebrities in the past, including Harry Styles and ASAP Rocky. Nevertheless, Jenner’s relationship with Simmons has been one of the most talked-about due to their multiple breaks and rekindled romance. With both the celebrities currently dating other people, it remains to be seen if they will ever reunite for the third time.