While the group discusses homeless and unemployed transgender people, Jenner says, "Don't, a lot of times, they can make more not working with social programs than they actually can with an entry-level job?"
"I'd say the great majority of people who are getting help are getting help because they need help," a friend answers.
"But you don't want people to get totally dependent on it. That's when they get in trouble. ‘Why should I work? I got a few bucks, I got my room paid for,'" Jenner responds, while the rest of the group appears visibly uncomfortable.
"Now I'm worried," LGBT activist Jenny Boylan later tells the camera.
"Caitlyn has every right to be just as conservative as she choses, but many transgender men and women need social programs to survive, and that's nothing to be ashamed of," Boylan says. "Living in the bubble is an impediment to understanding other people. Cait's going to be a spokesperson for the community. This is something she's going to have to understand."
In Jenner's revealing "20/20" interview with Diane Sawyer in April, the former Olympian said she is a Republican. When Sawyer asked Jenner if she cheered on Obama after he recognized the transgender community during a State of the Union address, Jenner replied:
"He actually was the first one to say the actual word transgender, I will certainly give him credit for that. But not to get political, I've just never been a big fan -- I'm kind of more on the conservative side," she said.
UPDATE: This post has been updated to reflect that the episode aired on Sunday, Aug. 2.
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