Caitlyn Jenner Struggles to ''Flirt'' With a Man, Admits She's Afraid of Rejection: ''That's Why I Didn't Date That Much''

See what happens when the E! star tries to mingle

By Jess Cohen Mar 18, 2016 4:02 PMTags
Watch: Caitlyn Jenner Struggles With Flirting Game

Caitlyn Jenner doesn't know how to "flirt."

When the I Am Cait star and her squad visit Chicago on Sunday's episode, they hit up the hotel bar to mingle and have a good time.

While at the bar, Caitlyn admits that she's "uncomfortable" because they're "in the middle of such a public place."

Caitlyn then reveals that the problem she has is "rejection" and explains "that's why...probably one of the reasons I didn't date that much."

She then tries to mingle with a man named Joe, but Candis Cayne doesn't think Caitlyn's very good at talking to men.

"Caitlyn doesn't really know how to talk to guys at all," Candis reveals in the video above. "With a flirt, with something more than who she is and so she doesn't know how to follow, she wants to lead."

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

Take a look at the video above to see what happens when Caitlyn attempts to mingle with Joe!