During the annual Jellyfish Festival, which welcomes back the Stinging Red Jellyfish to the shores of Springfield, Ned Flanders becomes depressed because he is alone. The other adults have partners with whom to spend a romantic evening at the Jellyfish Cotillion, and this is Ned's first festival without his wife Maude.
Ned returns to the Leftorium to work on his taxes and take his mind off things. There he meets a woman named Sara Sloane, who is after a pair of left-handed eyelash curlers. After chatting with Ned she asks him out on a date. After she leaves Ned notices a movie poster with Sara's face on it, which she is a movie star.
Sara and Ned hit it off, with Sara loving Ned's simple, quaint lifestyle and honesty. They go on several dates and encounter some problems, especially from tabloid reporters following them. Also, Sara is more uninhibited than Ned, causing some tension.
When her movie wraps, Sara asks Ned to return to Hollywood with her. Ned has a horrible dream about the bad things of Hollywood in a sequence that includes a cameo by series producer James L. Brooks, and also the "Hollywood" sign reading "Hollyweird", and refuses. Sara therefore tries staying in Springfield, to be with Ned. She slowly starts settling in with the locals, joining Marge's book club hosted by author Helen Fielding and going shopping with Ned.
At a concert, to which Sara wears a low-cut dress, Sara tells Ned she wants to have sex with him. Ned eventually relents, but insists on marriage if they are to continue a sexual relationship. Sara is unwilling to get married, and they break up and she returns to Hollywood. She gets a quickie marriage and divorce to Bob Balaban. Ned finds that he is now more attractive to women because of his famous relationship.