"Kimmy Kisses a Boy!" is the 5th episode of the Netflix original series, Unbreakable Kimmy Schmidt.
Kimmy's bunker-mate Cyndee visits New York with her new boyfriend, Brandon, whom Titus promptly outs. Charles makes his move with Kimmy.
Cyndee calls Kimmy one day to say that she’s coming to visit her in New York City. Kimmy tells Titus that he'll need to be especially helpful and nice to Cyndee. She reveals that she was kind of like Cyndee’s older sister in the bunker, and wants to look out for her. At the Voorhees’ house, Charles, Buckley’s tutor, kisses Kimmy, leaving her surprised and delighted. The next morning, Cyndee arrives, with her boyfriend Brad, whom she has had a crush on since middle school, when she was kidnapped. Once the two come inside, Titus pulls Kimmy aside to tell her that Brad is clearly gay. Kimmy laughs at his accusation at first, but Titus insists that he is, due to his gay-detecting skills. Later, Kimmy, Cyndee and Brad go out to lunch together. After a conversation, Kimmy learns that Cyndee has gotten everything she has so far by playing the sympathy card, telling everyone she is a mole woman. When she’s using the restroom, Brad daydreams out loud about other men. Kimmy accuses Brad of pretending to like Cyndee so he can share her fame, and is about to tell her, but Brad insists that he is only doing it because he’s a nice guy and he feels sorry for Cyndee. Kimmy reluctantly says she won’t tell Cyndee.
Later, Kimmy gets a call from Charles, who says that he’d like to go to the next level in their relationship and that he loves her. Kimmy agrees and says she loves him too.
While at the park with Cyndee, Kimmy is shocked when Brad proposes to her. She reveals Brad’s sexuality, but Cyndee admits she already knows, and that she just wants everything to be her way. Kimmy scolds her for cheating in life before leaving.
After a conversation with Charles, it turns out that he was accidentally butt-dialing Kimmy and that words he had said, he was saying to his friend while playing video games. Charles is surprised that Kimmy said she loves him, and says that they’ve only kissed twice and are going too fast. The two then break up.
Kimmy later apologized to Cyndee; she says that it’s not her place to tell her how to live her life. That’s the point of not living in the bunker. Kimmy tells Cyndee that she just used a shortcut, but that she’s taking a different route in life.