As Janeway and Tuvok leave for a diplomatic mission aboard a Kadi vessel, Neelix is left in charge of the Kadi ambassador on Voyager. Meanwhile, the Doctor determines that Seven of Nine needs the experience of dating in her socialization training. When he takes her to a holodeck bar for some practice making small talk with men, Seven buys a prospective suitor a drink in her usual dry manner. Once Paris learns what is going on, he makes a bet with the Doctor that Seven can't find a date for the Kadi ambassador's reception, and keep him for the entire night.
Knowing he has his work cut out for him, the Doctor tries to show Seven the importance of shared interests with a potential date. When he discovers Seven has a beautiful singing voice, the two engage in a duet of "You Are My Sunshine." Once her interests are determined, Seven peruses the ship's manifest for a suitable male and chooses a lieutenant whom she has worked with before in Engineering. Startled by her directness, the crewmate agrees to meet her in the holodeck for dinner.
When the Doctor tells Paris about Seven's progress, he realizes the Doctor is infatuated with her. The Doctor denies it, but he helps Seven fix her hair and pick out a dress to wear. In the holodeck simulation, he plays the piano as Seven and her date awkwardly navigate through a lobster dinner and a turn on the dance floor. When Seven takes the lead and tears a ligament in the man's arm, the evening is cut short, and she is ready to give up on dating altogether. However, the Doctor persuades her to keep trying and takes her onto the dance floor for a lesson.
Seven and the Doctor decide to attend the Kadi ambassador's reception together, and Seven displays all of her newly learned social skills. This prompts Paris to admit the Doctor has won the bet, which angers Seven. She accuses the Doctor of not having a sincere interest in her development and storms out of the party. Meanwhile, Neelix is losing control of the ambassador, who has had too much to drink and makes a scene before passing out.
The ambassador has a mighty hangover when his superior returns the next day, but he and Neelix manage to cover up what has really happened. The Doctor prepares to tell Seven about his feelings for her, but she comes to him first to thank him for his guidance. She announces that she will no longer require his lessons because there is not a suitable mate on board. Crushed, the Doctor hides his true emotions and returns to the holodeck bar for a lonely piano tune.