Filburt decides he is going to pop the question to the woman of his dreams, Dr. Hutchison, in spite of Hutchison's Mom and a possible romantic rival for the Doctor's affections. So Rocko tells him to call her on the telephone to do so. But as he does, Dr. Hutchison decides to do it tomorrow since she is having her high school reunion tonight. But Rocko tells him to do it now and plan to head to Hutch's house. He, Heffer, and Filburt drives to Dr. Hutchison's house so Filburt could pop the question to her, only to discover that she is leaving on a motorcycle with Tiger. Rocko, Heffer, and Filburt then come across Widow Hutchison, who tells Filburt to stick with his own kind and throws the car onto the O-Town freeway, where Filburt compels Rocko to follow Dr. Hutchison and Tiger.
Although they fight over directions before taking the wheel (as advised by Rocko,) they follow them to the parking garage of Waldoon's Department Store and end up in the elevator, which they take to the bridal boutique shop, where they spot Dr. Hutchison and Tiger. A nervous Filburt slowly walks towards Dr. Hutchison at an attempt to ask her to marry him, but ends up hallucinating. When he wakes up, he finds himself in Rocko's garage and Rocko tells him that Dr. Hutchison left without seeing him. When Heffer tells him that Dr. Hutchison went to the high school reunion, Filburt and Heffer implement a plan to sneak into the reunion to pop the question to Dr. Hutchison.
Rocko spontaneously shows up and Filburt gives him a disguise as the three sneak inside the reunion. They peek through the window to find Dr. Hutchison sitting at a table with Tiger. Rocko names the code Table 5 and the three sneak inside the gymnasium while under the table. Heffer leaves to set the Conglom-O Cake Detonator on the cake and shouts out "Cut the cake!" As Tiger leaves to cut the cake, Heffer returns under the table to inform that the cake is cut by the prom king (who is Tiger) and the detonator will cause the cake to explode as Tiger slices it. As he experiences the humiliation, Filburt will have time to pop the question to Dr. Hutchison. Rocko encourages Filburt to do it now while she is alone, but he decides to carry on their plan to stop Tiger. Rocko, urging Filburt to abandon the plan, demands that Tiger would never pass up an opportunity to marry Hutch, and neither should he, for they are together.
But just as Filburt is about to propose to her, Dr. Hutchison is called by Tiger because she was crowned by Prom Queen in high school. She walks to the cake and cuts it herself. Filbert tries to stop her, but it's too late, as the bomb causes the cake to explode through the gymnasium. When Filburt finally comes face-to-face with Dr. Hutchison, the latter offers him an engagement crown and asks him to marry her, which Filburt agrees to. It turns out that Tiger had instead encouraged Dr. Hutchison to propose to Filburt, and Filburt offers her an engagement hook. As Widow Hutchison chases after Heffer, thinking he is her former husband, everybody at the gym cheer for Filburt and Dr. Hutchison's engagement as the episode ends.