Caitlyn Jenner Struggles While Attempting To Flirt With A Man On 'I Am Cait'

On season 2 of the reality show I Am Cait, which follows the life of newly transgender Caitlyn Jenner, formerly known as Bruce Jenner, the star is put to the test while finding her way in the world as a transgender individual. Most recently, Caitlyn admitted that she finds various parts of her new way of life quite daunting.

[Photo by Dimitrios Kambouris/Getty Images for Yeezy Season 3]
[Photo by Dimitrios Kambouris/Getty Images for Yeezy Season 3]On the upcoming episode of the reality show, Cait seems to be thrown into a very uncomfortable situation by her group of friends when they hit the bar scene. as the Daily Mail shares.
"Caitlyn Jenner is left feeling out of her depth as she is pushed into chatting to men in a sneak peak of I Am Cait released Friday. The 66-year-old only recently opened up about the possibility of dating men but in an upcoming episode she is thrown into the deep end of the pool - and she seems to sink far more than she swims."
The clip shows Caitlyn and her group of friends heading to a bar in Chicago. Her pals Candis Cayne and Zachary Drucker spot a group of men and encourage Jenner to make her move. Caitlyn is clearly not impressed with their urging in the given situation.

Jenner's friends mingle, but Cait seems to be out of her element entirely and tells her stylist just that.

"I'm uncomfortable. It's in the middle of such a public place."
Cait goes on to explain the difficulties she has in flirting and communicates that it's not a new issue.
"For me the big problem that I have, with a lot of things, is rejection. [It's] probably one of the reasons I didn't date that much."
While at the hotel bar, Jenner is finally persuaded to strike up a conversation with a man named Joe, but as the publication shares, it really does not come across as flirting. The transition to her new style of life has been far from seamless for the former Olympic athlete. The star seems to be struggling but slowly finding her feet regardless of the criticism she has met from individuals in the transgender community.

Another situation that has been emphasized on numerous occasions lately is how much ex-wife Kris Jenner actually knew about then Bruce's desire to go through the transition to become a woman. In the second season of I Am Cait, an argument is started over the subject and during a recent interview with E!, Caitlyn shared her frustrations over Kris alleging that she was not open about her desires to change gender.

"Everybody has a different … interpretation of what happened, but I was, I thought, probably very honest with her at the beginning, when we first met 25 years ago. Now did I probably downplay it? Absolutely. Did I ever think eventually it would come to where I am today? No."
As People shares, the 66-year-old talked about Kris and the years they spent together in a very positive light, stating they "had 23 great years together" and that Kris, 60, is "a great person."

Recently, as aforementioned, Caitlyn has come under fire from members of the transgender community for her comments about various politicians she is in favor of. Activist Zoey Tur had some biting words towards Caitlyn after she showed support for Ted Cruz, The Wrap shares her words.

"Someone needs to tell Ms. Jenner she's transgender. There's great disappointment among people in the community."
 [Photo by Gerardo Mora/Getty Images]
[Photo by Gerardo Mora/Getty Images]Sarah McBride, another LGBT activist, shared her own opinion of Jenner.
"I'm definitely seeing a growing frustration within the LGBT community with Caitlyn's positions and actions. Her most recent comments about Ted Cruz were, for a lot of people, the last straw."
It's all a part of the process and a learning experience for Jenner, but perhaps she will be more sensitive in future.

[Photo by Pascal Le Segretain/Getty Images]