Kendall Jenner & Tyga Party at Usher’s 40th Birthday Party Along With Chris Brown — Was It Awkward?

There were two coincidental names on Usher's birthday party guest list: Kendall Jenner and Kylie's ex, Tyga. Find out how they reacted at the venue, and the surprise 'life of the party,' which HL has the EXCLUSIVE scoop on!

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October 16, 2018 2:34AM EDT
Tyga & Kendall Attended Usher's Birthday Party
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Image Credit: Courtesy of The h.wood Group

A parade of celebrities crowded in Los Angeles’ Delilah restaurant to ring in Usher’s 40s on Oct. 14, but two of them had an interesting history together! Kendall Jenner, 22, and her little sister’s ex-boyfriend Tyga, 28, were among the partygoers. Would this mark Tyga’s second time he’s had a publicized run-in with Kylie Jenner’s family, following his breakup with the Kylie Cosmetics CEO in early 2017? We learned what really went down. “Kendall and Tyga didn’t interact, basically they were on opposite ends,” an eyewitness at the party EXCLUSIVELY shares with HollywoodLife. And our source spills if that was intentional.

“They weren’t really avoiding each other, they were just occupied by their own friends and didn’t interact,” our eyewitness adds. “Kendall, Luka [Sabbat] and Justine [Skye] arrived together with a couple other friends and stayed for an hour, then left.” Meanwhile, Tyga arrived with a surprise guest: hip hop legend Chris Brown! Even if Kendall and Tyga didn’t use the party as a reunion, we learned even more details about the star-studded bash! “Chris Brown stole the mic to personally wish Usher a very happy birthday and Kevin Hart and Diddy [Sean Combs] each gave a speech as well,” our source goes on. “Usher was seen dancing and socializing often with his friends and family and even gave a thank you speech. Guests received baseball caps with an A on them as party favors as Usher blew out the candles on his chocolate cake with guests singing ‘Happy Birthday’ as a sendoff into the evening.”

The party favors were a tribute to Usher’s new album A, released on Oct. 11, which the DJ span tracks from. “His new album got everyone dancing as well as his older hits including ‘Yeah’ and ‘You Make Me Wanna.'” But there was one person who especially partied it up! “The life of the party was Chris Brown who was dancing and smiling with friends well into the evening,” our eyewitness reveals, whom Tyga was seen dancing with, alongside other friends, “in front of the DJ by Usher’s table.” Our source points out Chris was in a “great mood” and “seemed very happy.”

Courtesy of The h.wood Group
It’s no surprise that Kendall and Tyga didn’t make a big deal about their shared dance floor space. The “Taste” rapper, who once performed at Kendall’s Sweet 16, was put in a much more awkward situation after he bumped into Kim Kardashian and Kris Jenner at Beyonce and JAY-Z‘s On The Run II Tour on Sept. 23! Instead of making a scene, Tyga went in for a hug with Kylie’s older sister and mom. And we learned why Kylie’s OK with her ex-boyfriend turning up at the same events as her family! “Kylie has no problem with her family remaining on good terms with her ex, Tyga,” a source close to Kylie EXCLUSIVELY told HollywoodLife on Sept. 24.“He was such a big part of her life and her family’s life for so long, and she understands why they are still amicable with him.”
Tyga, Diddy, Chris, and Kevin were photographed taking a celebratory shot with the birthday boy, as you can see above! We also learned that Scooter Braun, the manager of Ariana Grande and Justin Bieber, and Dawson’s Creek star Joshua Jackson, were also in attendance.