Following directly from the previous episode, all of Martin's hopes seem shattered when Kate appears unimpressed, but, touched by his clumsy attempt at romance, she finally accepts his offer of a date . . .

Martin finds his bar mitzvah bonds in a closet and suddenly has extra cash. Toby encourages him to invest $5,000 in a fledgling business she is setting up offering stock tips over the phone, 555-TIPS. The business goes terribly, until a wrong number mistakes it for an S&M phone-sex chat line and stays on for hours. Seeing where the real money is, Toby employs the services of her family – Gina, Angie – in order to cover the phones.

Martin and Eddie attend their school reunion, where Martin is eager to make up for lost opportunities with a recently-separated old flame.

Martin dates a woman that acts strange in public, and yet, is an etiquette expert.