Georgiana is embarrassed about her inability to flirt. Because she grew up in such a sheltered bubble, she never learned how to date men who were not already part of the social fabric of her life. Due to her inexperience, she is unsure how to handle her crush on Brady. One afternoon, as she leaves work and heads out to play tennis, Brady stops her so that they can walk together and invites her to play a tennis match with him the next evening. They start playing tennis together on a regular basis and learn more about each other. Georgiana is impressed and intimidated by Brady because he has more practical experience of the world. Georgiana is close enough with Cord to hint at her new romance at work. When Georgiana meets her parents at the townhouse, she is annoyed that Sasha is there because she thinks that Sasha tries too hard to be liked. In an attempt to start clearing out the house a bit, Sasha asks Georgiana to organize the childhood items that she wants to keep.

After a two-weeks business trip, Brady returns and plays tennis with Georgiana again, kissing Georgiana for the first time. After their next tennis match, Georgiana invites Brady over to her apartment, and they have sex.