At the Krusty Krab, Frankie is ordering food for Evelyn. He does not realize that Squidward was on his break and cannot read his sign. Evelyn sees that he cannot read and reveals that she can't read either, so they comment that they were meant for each other. Learning that his books about love are only "torturing" him, the depressed Squidward throws away his book and impacts on evil widsom SpongeBob. When SpongeBob tries returning the book, Squidward claims the book is "just a cruel reminder that I'm single, and likely to remain that way." SpongeBob tries cheering Squidward up by pointing out that while he's currently never found true love, that doesn't automatically mean he won't ever find it, and says, "There's a squid for every pot!," but Squidward complains about that being a very clichéd saying.
Just then, a female customer walks in and Squidward becomes instantly smitten with her. The woman admires the "decor" and Squidward believes that she's perfect since they seem to have the same interests and hobbies. Squidward decides to ask her out on a date, but when she comes up to the register, and Squidward's too nervous to ask her out on a date. Just as the woman is about to leave the restaurant, SpongeBob turns on the motor that's in the boat containing them and the register, and manages to prevent her from leaving. Squidward's still too nervous and love struck to say anything to her, so SpongeBob introduces them to each other, during which it's revealed that the woman's name is Squilvia. After SpongeBob tells Squilvia about Squidward, she agrees to go on a date with him later that night.
After she leaves, SpongeBob points out that Squidward was pretty nervous back there and asks him about the last time he actually went on a date. Squidward gets even more nervous when he realizes just how long it's been since the last time he actually went on a date, so SpongeBob offers to help him prepare for it by making him go on a "practice date." As practice for the real date, he was tested at SpongeBob's House on complimenting about his date, giving flowers, driving to dinner, and having dinner which all annoy him. He was driving in a circle from and to SpongeBob's house (which would be where the restaurant is). At the "restaurant" (SpongeBob's roof), Patrick is serving plastic dinner which he literally took a bite on. When Squidward had enough, he left and shouted angrily over how it was pointless. He went down the stairs, and SpongeBob convinced Squidward to come back, but his shoe gets caught, causing him to fall down the stairs, revealing his true identity.
Squilvia showed up and reveals that Squidward's true personality was better than what she expected. SpongeBob comments that his work was done, only to find Patrick in drag, demanding a movie and plastic popcorn.