'I Am Cait': Caitlyn Jenner Struggles To Flirt With Men In This Sneak Peek [VIDEO]

Caitlyn Jenner isn't quite ready to enter the dating world just yet. In a sneak peek for the Sunday, March 20 episode of her hit E! docuseries "I am Cait," Jenner opens up about what's holding her back from putting herself out there on the singles scene.

In a sneak peek for tonight's episode, Jenner and her girlfriends are visiting Chicago, and while they have some downtime, they decide to hit up the hotel's bar to mingle with other guests. Her gal pal Candis Cayne immediately surveys the crowd and then sets off on the prowl.

"There's a lot of boys around," Cayne says before heading off to go mingle with some of the well-dressed business men, setting her sight on a table full of men, but Jenner hangs back at the table with her other friends.

"Um," Jenner tells one of her girl friends in the clip. "I'm uncomfortable. It's in the middle of such a public place."

"For me, the big problem that I have in a lot of things is rejection," she reveals in her on-camera interview. That's probably one of the reasons why I didn't date that much."

Meanwhile, Cayne takes at seat at the head of a table, chatting with four men. Another friend sparks up a conversation with another man by the bar, and both ladies flirt and work their charm. While Jenner is still seated, a man walks up to her and introduces himself.

"What's your name?" Jenner asks the gentleman named Joe, who's dressed in a black suit, white collared shirt and black tie.

"She doesn't really know how to talk to guys at all," Candace tells the cameras. "With a flirt, with something more than just who she is and so, she doesn't know how to follow. She wants to lead."

The camera cuts to a shot of Jenner awkwardly noshing on some appetizers while making small talk with Joe.

"Well Joe, it was nice meeting you," Jenner says, extended her hand for a handshake and asks what he does for a living. He says he works in real estate, both commercial and residential.

"Wherever," she says, nodding. "Wherever you can make a buck."

"Sometimes when you're talking to guys, you have to take the backseat a little bit," Candace explains. "I don't know if she's ready to do that"

Watch the full sneak peek below and be sure to catch tonight's episode of "I Am Cait," airing at 9 p.m. on E!

Real Time Analytics