Rebecca tries to stick to her plan for happiness while Nathaniel and Maya bond over their feelings of unrequited love.
"Gratuitous Karaoke Moment" (sung by Scott Michael Foster and Esther Povitsky)
- Hollywood Tone-Deaf: Lampshaded."Relatably, we're both off-key
But it's the part of the film
That everyone likes"
- Musical Pastiche: Of "The Start Of Something New" from High School Musical.
- Bromantic Foil: In the romcom fantasy, George is cast as the confident jock best friend to Nathaniel's homely dork.George: Only things I care about in this world: sports, your love life.
- Disposable Fiancé: The romcom fantasy casts Greg as Rebecca's douchey, shallow boyfriend whom Nathaniel seeks to undermine. Marcy (Maya's ex's new girlfriend) is the personality-less one.
- Genre Deconstruction: The entire episode is a Deconstructive Parody of romantic comedies, to the point of practically being a Deconstructor Fleet. Nathaniel and Maya start out as "uggos," try to woo their exes back by pretending to go out, go through a magical makeover, actually start to have feelings for one another, have a gratuitous karaoke scene, and then have a big moment where Nathaniel realizes that he's in love with Maya...except not really, because "Maya" is still just a stand-in for Rebecca and he learns that for her to be happy, he has to let her go.
- The Glasses Gotta Go: Maya has to lose her glasses as part of her makeover. In an exaggerated example, Nathanial now has glasses just so he can lose them as part of his makeover.
- Grand Romantic Gesture: Fantasy!Nathaniel plans to interrupt Greg's restaurant opening with a big speech telling Rebecca how much he loves her, but he backs out at the last second because he realizes Maya is the one for him.
- I Want My Beloved to Be Happy: What Nathaniel ultimately realizes he has to do.
- Makeover: Both Nathaniel and Maya have one in the It Was All A Dream rom com parody.
- Mean Boss: The normally amiable Bert is cast as a snobby Amoral Attorney and overall Miranda Priestly-esque harsh boss.
- Operation: Jealousy: In the parody, Maya and Nathaniel pretend to date to make Rebecca and Maya's ex Joanne both jealous.
- Opposites Attract: Parody!Nathaniel and Maya.Nathaniel: We're that mismatched couple from different worlds that can make it.
- Purely Aesthetic Glasses: Maya doesn't need glasses, she just wears them to honor Velma from Scooby-Doo.
- Romantic FakeReal Turn: In the fantasy, Nathaniel and Maya start out fake dating but then Nathaniel catches feelings.
- She Cleans Up Nicely: Maya, after her makeover. It's even lampshaded early into the fantasy that she could be a stunner if she tried harder.
- Shout-Out: To many classic rom coms, including Bert as the "evil demanding boss" from The Devil Wears Prada. He asks for a sixth book in the The Millennium Trilogy series, similar to how Miranda asks for the as-yet-unpublished next installment in the Harry Potter series.