Martin's divorced father Mickey comes back to live in New York. Martin fixes him up with Toby's mom Angie on a dinner date. He takes her home, but to Toby's irritation ‘does nothing' to her. Martin visits the one- bedroom apartment Mickey is sharing with apartment owner Roger.

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.

The beautiful widow of a famous author brings a new unpublished novel by her late husband to Martin with the one caveat that he cannot reveal the true origin of the book, thus giving Toby the opportunity to accept the kudos for the bestseller.

Under pressure from Gibby to get an elite writer, Martin attempts to lure the writer dating Toby (who coincidentally, is an award-winning author).

Toby is in a rut. Uses self-help book.

Martin's friend likes Toby.