The family heads to the mall to pick up costumes for Hilary's Halloween party, while Will and Carlton place a bet to see who can find a date for the party. Philip gets held up at a gadget store. Vivian sings in a recording booth, where she receives positive feedback and a large audience standing outside listening to her. When Hilary forgets to take a hat off of Ashley and walks out of the store with it, they are accused of shoplifting. Will and Carlton both spot a woman, Melinda, and run to her, ending the episode on a cliffhanger.

It is Geoffrey's birthday and Will decides to set him up on a blind date with an English woman named Helen as a gift. Will, thinking she is better for him, figures she will be turned off by his stodgy attitude. However, Geoffrey ends up having a great time with her. Geoffrey also gives Will an insight about prejudging others and that some men view birthdays as a time to reflect on one's life, not party.