Jessica is concerned when she learns that Evan's got a girlfriend (played by Julia Garcia), worried it will affect his grades. Meanwhile, after Honey and Emery convince Louis to see You've Got Mail, he admits a shameful secret from his past.
- Bait-and-Switch: In The Tag, Louis makes various "You've got mail" puns, such as putting on a documentary about sea life to say "You've got whale". But when the actual mail arrives, he just says "Mail's here", to everyone else's confusion; when Jessica reacts by asking if he's serious, Louis just points to the envelopes Emery picked up and says the mail is indeed here.
- For Your Own Good: Jessica convinces Evan not to have a girlfriend at his age because of this. However, when Evan becomes despondent enough to completely wreck a perfect recreation of "A Sunday Afternoon on the Island of La Grande Jatte" he'd painted on a mug, Jessica realizes the emotional harm she's done and gets them back together.
- Gaslighting: Jessica is concerned that Evan having a girlfriend will distract him from his studies, so she takes his report card and lowers his grades to convince him it's already happening. She admits the truth after seeing how devastated the resulting break-up has made Evan, which infuriates him until he sees that she's also helping get them back together.
- My Greatest Failure: After seeing You've Got Mail, Louis admits that, when he founded Cattleman's Ranch, he unintentionally ran a different, smaller-scale restaurant out of business, comparing the situation to the struggle between "Fox Books" and "The Shop Around The Corner" from the movie.
- No Good Deed Goes Unpunished: Determined to do right after admitting his greatest regret, Louis tracks down and hires his former competitors...only to learn that they are horrible cooks whose restaurant was closing regardless of his presence. And when he has to let them go, they try to file a wrongful termination lawsuit against him, requiring him to keep them around and pay them for odd jobs for at least a few more weeks.
