An Official Timeline Of Kendall Jenner and Ben Simmons’ ‘Casual’ Relationship

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Unlike her famous sisters, Kendall Jenner’s rarely involved in relationship drama. Until now.

The 24-year-old has been in an on and off-again relationship with Ben Simmons since 2018. And right now, it looks like they’re on again (sort of!).

Simmons, 23, is a professional basketball player for the Philadelphia 76ers. So he’s no stranger to the spotlight.

Before entering a relationship with Jenner, he dated singer Tinashe until May 2018. The two weren’t together long. And it took Simmons no time at all to move on.

He started dating Kendall that same month.

Gettyimages | James Devaney

Simmons and Jenner were officially dubbed "an item" after they were seen cuddling in July.

(See video below.)

That same month, a source told Us Weekly, the two “are still hanging out quite a bit” and "are dating and exclusive, though not ‘official.’”

Confusing, right?

Whether the two were “officially” together at that point or not, they seemed tight. Especially when they celebrated Ben’s birthday together at the end of the month.

In August, the couple even went on vacation with Khloe Kardashian and her baby daddy, Tristan Thompson.

Gettyimages | Mitchell Leff

Things took a turn in September when Kendall was spotted making out with Anwar Hadid, the brother of Gigi and Bella Hadid.

The kiss seemed to confirm the end of Jenner and Simmons' relationship.

Their “break up” didn’t last long though. In November, TMZ obtained footage of the couple together, sparking reconciliation rumors.

The rumors only continued after Kendall attended several of Ben’s games with his mom. And in January, Simmons left the comment "come here" on Kendall’s Instagram post.

Gettyimages | Don Arnold

Unfortunately, the good times didn’t last. The couple reportedly took another break in May of 2019.

But, as of now, they’re back together...in a "casual" kind of way.

On New Year's Eve, they were spotted spending the weekend together in New York. And apparently, they looked very much like a couple.

But even with their public display of affection, it looks like their relationship isn't very serious.

“Kendall and Ben are not officially back together,” a source told Us Weekly.

Gettyimages | Vaughn Ridley

“They both like having a no-strings-attached type of relationship with each other, for the most part. They both work and travel frequently and don’t find it very realistic to be in an exclusive relationship with one another. They do really like each other though and love spending time together,” the source continued.

So while the couple might not be official, chances are, they will be soon.

And although their on and off-again relationship might seem messy, these two clearly have strong feelings for each other.

After all, Ben is Kendall’s most publicized relationship, not including her romance with Harry Styles back in 2013.