The episode begins with Caitlyn sitting down with her assistant Courtney and her boyfriend Johnie. During a casual conversation, Caitlyn and Courtney begin questioning Johnie how he would react if someone he was dating came out as transgender. Courtney asks, “If I told you right now that I was [trangender], would it change us? And would you continue?” In which, Johnie answers, “Yeah (it would change us), but then we could choose to continue to be friends.”
Johnie makes it evident that society isn’t in a place where being transgender doesn’t change things when it comes to dating.
Afterwards, Caitlyn has a lunch with her transgender friend, actress Candis Cayne. At lunch, Candis talks about how nervous she is about her upcoming auditions she has for a role in a movie with Katie Holmes. She tells Caitlyn that she finds that she has a whole other layer of insecurities going into the movie business as a transgender.
Later, Candis convinces Caitlyn to go to The Abbey, a West Hollywood gay club. Here, Caitlyn expresses that she feels uncomfortable being around all the dancing and exposed male dancers. While the other trans-women playfully flirt and watch the male dancers, Caitlyn is visibly put-off by the club setting.
At this point, Candis tells the one-on-one camera that she is pretty certain that Caitlyn is attracted to women.
Soon after, Caitlyn sits down for lunch with her other trans-friend, Jenny Boylan. Here, Jenny tells Caitlyn that she seems much more at ease than she did when they first met about two months ago. She also questions Caitlyn on whether she has begun playing the field, in terms of dating yet. Caitlyn reveals that she hasn’t really even thought about dating, but tells Jenny that although she’s “always been with women,” she would be very attracted to a “guy [that treats her] like a woman.”
At this point, Jenny is worried about Caitlyn’s reliance on others to make her feel like the woman she is. Jenny tells her that she shouldn’t have to look to men to validate who she really is, telling her, “You are a normal woman. You don’t need a man to make you a woman.”
At dinner with her fellow female transgender friends, Caitlyn continues to discuss what dating is like in the trans-community. The women share different stories demonstrating the difficulties they face when trying to date. Many of them have been stood up on numerous occasions once they revealed that they are trans. They also express that as trans-women they are often taken advantage of, since often men believe that trans-women have lower standards.
Later in the episode, Candis tells her friend Chandi that she has pretty much given up on dating. She says she doesn’t feel any hope when it comes to finding a man who is willing to accept her despite her past struggles with gender. Jokingly, she tells Chandi that maybe “she should just date [Caitlyn].”
The show has been hinting at a romantic relationship between Caitlyn and Candis since the early promos. However, multiple sources close to Caitlyn claim that this is merely a stunt to draw in viewers.
At the end of the episode, Caitlyn and Candis visit a summer camp that is for transgender kids. At the camp, Caitlyn and Candis listen as many of the young campers open up about their struggles growing up as a transgender. They also express appreciation for the camp and being able to feel confident and normal as a transgender there. It is clear that listening to the young campers being open about their feelings and identities is inspiring to both Caitlyn and Candis.
After seeing the kids embrace their true selves, Candis and Caitlyn decide to seek the help of a matchmaker. However, Caitlyn makes it clear that she is just there as support for Candis, but eventually decides she will fill out a chemistry analysis for fun. While completing the survey she admits that in terms of physical attraction she is confused, saying, “Physically, I don’t know where I’m at.”
The result of the analysis reveals that Caitlyn should be dating someone who is also her best friend.
The show continues to push the idea that Caitlyn and Candis may develop a relationship that is more than just a friendship. This seems especially apparent when Caitlyn gifts Candis with a Lamborghini to drive around while her car is in the shop and says she “doesn’t know what the future holds when it comes to dating,” as her and Candis drive off into the sunset together.
Next week, Caitlyn’s ex Kris Jenner comes and visits her for the first time since her full transition. Caitlyn says she feels its finally time to talk things through, since her and Kris have been very distant for the past year or so.