‘KUWTK’: Khloe Kardashian Dares Kris Jenner to Chat Up Strangers and She Hilariously Accepts the Challenge

Leave it to the Kardashian-Jenners to always know how to have the best time, no matter where they go. In the latest Keeping Up With the Kardashians promo video, they decide to bring joy to others during a wine tasting and even dare Kris Jenner to chat up some people who end up being huge fans.

Kris Jenner, Kim Kardashian, Khloé Kardashian, and Kourtney Kardashian accept The Reality Show of 2019 for 'Keeping Up with the Kardashians' on stage during the 2019 E! People's Choice Awards
Kris Jenner, Kim Kardashian, Khloé Kardashian, and Kourtney Kardashian | Christopher Polk/E! Entertainment/NBCU Photo Bank

KUWTK goes to wine country

In the newest KUWTK teaser for season 18, some of the family chill with wine in Napa Valley. Rather than keeping to themselves, however, they decide to mix in a bit with the other people at the winery. It starts with Khloe Kardashian paying a sweet compliment to another patron about her colorful hat and outfit.

Khloe quickly discovers the power of giving a compliment to a stranger and how it can brighten their day so much. She tells the woman, “I love your beret so much,” to which the stranger says, “Oh my god, you’re so beautiful.”

She pays another compliment, saying, “You’re so beautiful, you look so fabulous.” and they trade sweet comments to each other.

“You guys gotta start complimenting people, it makes them feel so good,” Khloe tells her family.

Khloe dares mom Kris and she runs with it

Discovering that giving a stranger some praise makes them happy, Khloe challenges her mom Kris to do the same. “This is your dare: I want you to go up to someone at a table, stand up, and I want you to go give them a compliment,” she states.

Kris didn’t find the dare to be that much out of her comfort zone, as she shared she’s always talking with people and complimenting them.

The momager starts by yelling from her seat, “You look beautiful,” which elicits a response, so she gets up to get some face to face time with her new friends. The woman, it turns out, is a fellow Scorpio whose birthday is one day after Kris’ and they share a hug. The matriarch then pays a compliment to a man wearing a cowboy hat and sleeveless shirt, telling him, “You look stunning.”

She even takes a cigarette out of his shirt, gets a light, and takes a puff. Bold!
 
“My daughter and wife just love you all to death,” the man tells Kris and then shouts to Kim, Khloe, and Kourtney, “Damn good-looking family! Almost as good looking as we are.”
 
“Almost!” Khloe replies. “We’re not there yet.”
 
Kris leaves her cigarette behind, but calls it “the greatest puff in the world.” “You’re a sweetheart, I’ll tell you what,” the man tells Kris. “And just prettier in person.”
 

Kris returns to her family, proud that she handled the dare with ease and asks, “who’s going to be next?” She then tells Khloe and Kourtney to share their wine, which they do with another group, and it’s all slightly awkward but they pull it off.

Kim isn’t game for a dare

When Khloe and Kourtney return, they think it’s Kim’s turn to step up, but she’s not having any of it.

“No, the dare is that I’m coming on a wine tasting trip,” she says as she looks at her phone. It’s clear from her body language that she wants no part of this family activity.

As the family gets up to leave, Kris cautions Khloe about her coat and potentially knocking over wine — and, sure enough, she breaks a glass. Kris turns to see what happened and Khloe tells her to keep walking!