Tired of the kids constantly asking him for money, Dave puts them on strict allowance. Vicky supports her husband until she, too, is put on a budget and is unable to buy the Prada boots she's had her eyes on for years. When Larry spends his entire allowance the first day at Medieval Times, he asks Mike for money and Mike turns into a loan shark, while Hillary starts an escort service for the nerdy boys at school to earn extra money.

Vicky's mom Betty and her boyfriend Sid (George Segal) announce their engagement and upcoming wedding in St. Martin and invite the entire family to join them. But when Sid goes too far with a stripper, Dave wonders whether or not to tell Betty and risk losing the free trip. Kenny goes on a date with an ex-boyfriend of Hillary's so Dave has an awkward conversation with him about gay safe-sex, while Hillary worries she may have a knack for turning men gay.