After seeing how easily her father responded to a bumbling but beautiful delivery girl, Maya complains that good looking people get all the breaks. To prove her point, she suggests sending two men, one handsome but stupid and the other well qualified but homely, to apply for the same job. Meanwhile, as Jack struggles to assemble a toy for his baby daughter, Elliott enlists Nina in a practical joke on Finch. After meeting the handsome Derek and the well qualified Neil, Maya sends them out to interview for a job. But Maya's thesis quickly runs into trouble. When Neil returns with news that he's a shoe-in for the job and asks her out for dinner to celebrate, Maya is careful to turn him down, citing journalistic ethics as her reason. However, when Derek returns to announce that he got the job, she accepts his offer for a date. Meanwhile, as Jack struggles with the unassembled toy, Nina helps plan a practical joke that plays on a lifelong fear of Finch's. While at dinner with Derek, Maya runs into an old high school classmate who's impressed with her handsome date. After inviting Derek to her high school reunion, Maya does her best to cover their relationship at work. However, when she can no longer keep it under wraps, she must fend off accusations of hypocrisy. Meanwhile, as a safety recall of the toy gets Jack off the hook, Nina springs her surprise on Finch, only to discover that the joke was really on her. But when Jack sees what's happened, he sends Nina on a Caribbean vacation while giving her work to Elliott and Finch as Maya finally decides to break up with Derek.