Liz walks in on Jenna and Paul doing their makeup and trying to achieve a touchless orgasm. Jenna is excited that the two are celebrating their six-month anniversary. After a conversation with Jenna, Liz begins to question if the spark is gone when it comes to her relationship with Carol.
Tracy's "son" Donald has come up with the idea to open a new themed restaurant in Times Square. Now he just needs the money. He propositions Jack to invest in his restaurant, where guys dressed as monsters from old Japanese movies will attack each other as people eat and watch. Jack is appalled.
Jack tells Liz that it's time for her to seek a therapist and work through her relationship issues. She confides in Kenneth and begins to open up about where all of her issues with men stem from, going back to her childhood when she found out Santa was a "fat fraud."
Jenna fears her relationship with Paul is going downhill because he wants her to meet his parents. Liz tells Jenna that she's only freaking out because she's in love with Paul. Later that evening, Jenna tries to set up a sex tape with Paul but it backfires. Paul calls Jenna out on her fear of commitment. Paul decides to end his relationship with Jenna. He'll pick up his panties the next day while she's at work.
Jack has his own breakthrough moment after talking to Kenneth. Jack realizes that all his personal issues stem from his father, who always tried to crush his dreams. Jack rushes to Tracy and tells him to not follow his original advice of crushing Donald's dreams, but instead, Tracy should support them, no matter how crazy they sound.
