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Things could have gotten awkward in the early morning hours of Thursday (June 6) when Kylie Jenner was briefly at the same club as her famous sisters’ exes!

Kylie was hanging out at Delilah nightclub in West Hollywood, California when Khloe Kardashian‘s ex Tristan Thompson and Kendall Jenner‘s ex Ben Simmons both stopped by.

The pair arrived shortly before 2 AM, which is around when the club would close.

It’s unclear if they ran into each other, though TMZ notes that Ben left about five minutes after arriving and adds that it could be because of an awkward run-in.

Head to TMZ to watch the video.

If you don’t know, Tristan and Khloe split earlier this year after he cheated with Kylie‘s BFF Jordyn Woods. Kendall and Ben reportedly took a break from their relationship last month.

Kendall Jenner is having some fun in the sun with Luka Sabbat.

The 23-year-old Keeping Up With The Kardashians star and model and the 21-year-old The Dead Don’t Die actor and model were spotted sunbathing on Thursday (May 23) during the 2019 Cannes Film Festival in Cannes, France.

PHOTOS: Check out the latest pics of Kendall Jenner

Kendall looked hot in a polka dot bikini while she enjoyed some downtime.

This is the first time Kendall‘s been spotted since news broke of her reported “break” with Ben Simmons.

“The relationship ran its course. She’s spending time with her friends and back to being in fun mode,” a source says of their relationship. Click here for more!

FYI: Kendall is wearing a Wanderlust bikini.

Kendall Jenner and Ben Simmons are slowing things down.

The 23-year-old model and the 22-year-old Philadelphia 76ers player are “on a break,” a source told People.

PHOTOS: Check out the latest pics of Kendall Jenner

“The relationship ran its course,” the source added. “She’s spending time with her friends and back to being in fun mode.”

The news comes just a few days after Kendall opened up about her relationship with Ben with Vogue Australia.

Kendall and Ben have been linked to each other since May 2018.

Kendall Jenner holds hands with boyfriend Ben Simmons as they arrive at dinner at Zuma restaurant on Wednesday night (February 13) in New York City.

The 23-year-old model tried to keep a low profile under a black, leather bucket hat along with a matching leather jacket while the 22-year-old NBA player kept things cool in a black sweatshirt for their Valentine’s Day Eve date.

PHOTOS: Check out the latest pics of Kendall Jenner

The couple also stopped by Marquee New York for an early Valentine’s Day celebration.

The following day, Kendall looked pretty in a red blouse and black jeans as she was spotted leaving her hotel as she stepped out for the day.

Kendall Jenner and Ben Simmons are still going strong!

The 23-year-old model and the 22-year-old NBA player were spotted leaving The Mercer hotel on Friday (February 8) during fashion week in New York City.

Kendall, wearing a black and tan ensemble, made her way to Root Studios.

That same day, Kendall changed into a neon green top with matching printed pants, a black jacket, and red and yellow sneakers while going shopping with Kourtney Kardashian at What Goes Around Comes Around.

Kourtney looked chic in a black and white outfit featuring a long coat and heeled boots.

The night before, Kendall and Ben coupled up for a dinner date.

FYI: Kendall is wearing a Claudia Li leather jacket. Ben is wearing Burberry pants and Nike Jordan sneakers.

Kendall Jenner heads out for dinner with boyfriend Ben Simmons on Thursday night (February 7) in New York City.

The 23-year-old model is in town with sisters Kim and Kourtney Kardashian for fashion week. Ben joined her for his day off from playing in NBA basketball games.

The couple kept a low profile while arriving at the Mercer Hotel earlier in the day.

Ben and his team, the Philadelphia 76ers, will be facing off against the Denver Nuggets on Saturday night. They then will play against the Los Angeles Lakers on Sunday afternoon.

30+ pictures inside of Kendall Jenner and Ben Simmons out for dinner… More Here! »

Kendall Jenner makes a quick dash out of her ride as she arrives at the Mercer Hotel with boyfriend Ben Simmons on Thursday night (February 7) in New York City.

The 23-year-old model tried to keep a low profile under a Dsquared2 hat, sunglasses, and a black puffer jacket while the 22-year-old NBA player looked cool in an acid-washed denim jacket and white sweatpants as they arrived in the city for NYFW.

PHOTOS: Check out the latest pics of Kendall Jenner

The day before, Kendall joined younger sis Kylie Jenner for a photo shoot at Milk Studios in Los Angeles.

10+ pictures inside of the couple stepping out…More Here! »