Is 2020 the Year Kendall Jenner Will Finally Stop Running Back to Ben Simmons?

Kendall Jenner isn’t the only person in her family who seems to be constantly embroiled in relationship drama. For Jenner, however, much of the drama centers around one particular basketball player: Ben Simmons.

The two have been in an on-again-off-again relationship since 2018, although by May of 2019 it seemed that their relationship was over. But recent events have called that into question yet again. Will Jenner and Simmons ever figure out what they want?

Kendall Jenner and Ben Simmons have a long, complicated timeline

Kendall Jenner attends the Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute Gala
Kendall Jenner | Matt Winkelmeyer/MG18/Getty Images for The Met Museum/Vogue

Jenner and Simmons have surprised people by showing up together at more events than there’s space here to cover. Their volatile relationship seems to have started somewhere around the beginning of June 2018. They were seen being cozy and shopping together, which fans found a little confusing, considering that around the same time Jenner had been kissing Anwar Hadid.

The relationship with Simmons seemed to be enduring, though, and the two were spotted together many times over the summer. They even went on a vacation together in August. That made it even more surprising when rumors went around in September that she was again seen making out with Hadid. She was definitely hanging out with his sisters.

Whatever may have happened with Hadid, throughout the winter Jenner and Simmons spent a lot of time together. She showed up at several of his basketball games, sometimes with his mom. They went to Drake’s 2019 New Year’s Eve party together, and they celebrated Valentine’s Day together. 

Kendall Jenner and Ben Simmons’ relationship gets even more complicated

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In May, Jenner appeared on the cover of Vogue Australia and spoke to the magazine about her relationship with Simmons. She gave some mixed messages about it, hinting that an engagement ring might be in her future someday, but also saying that she didn’t think it was fair to talk about what was happening because she didn’t know exactly where it was going. 

The confusing statements soon became clear when the couple broke up shortly after that interview. Sources close the couple said their “relationship ran its course.” That sounds pretty definite, and you might expect the next scandal would make that breakup permanent. 

Kendall Jenner was accused of dating too many basketball players

That summer a rumor circulated that Jenner was dating an L.A. Lakers star, Kyle Kuzma. Simmons’ sister, Liv Alice Simmons, tweeted that Jenner was too active in the romantic lives of basketball players, saying: “I just wouldn’t wanna be known for dating athletes. Like imagine working your way through a league. Not a team a LEAGUE!”

It turned out that Jenner and Kuzma weren’t dating at all. They’d just been at the same party, but the damage was done.

A meme circulated saying that Jenner had dated five basketball players. She clapped back, saying that she’d only dated two. 

Kendall Jenner and Ben Simmons might have reunited

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With all this history behind them, you’d expect the two would stay away from each other. However, in December of 2019, Jenner was seen at Simmons’ basketball game. That raised eyebrows, but what came next was even more surprising.

On New Year’s Eve, Simmons rented out a rooftop restaurant in Philadelphia to ring in the new year. Reports soon went around that he and Jenner arrived about a half an hour before midnight and stayed long enough for the countdown.

That hardly sounds like the behavior of two people whose relationship has run its course. If history tells us anything, Jenner and Simmons are back together again. Will this time lead to “happily ever after,” or will they finally call it quits for good? We’ll just have to wait and see.