Having lost her restaurant in a divorce settlement, Wally decides to buy an old Manhattan bar where she meets columnist Jack. Though they are complete opposites they find each other interesting, even though she is preparing to ruin his favorite hangout.

Jack becomes acquainted with Kip, Wally's impressive ex-husband. Wally invites Jack to dinner but he misinterprets her intentions.

Jack and Wally have their first date at a new high-class restaurant and it does not go well, particularly when it comes time to pay the check. Meanwhile, Nadine tries to remake the Blue Shamrock's customers.

Jack is too tied up with work to attend the newly refurbished Shamrock's grand re-opening, but Wally's ex-husband Kip is there to make her feel better.

Jack asks Wally to accompany him to a press-club dinner where he is to receive an award, but asks her to wear something sexy.

Jack takes Wally on a weekend getaway to see the fall colors, but his obviously inadequate planning starts to drive her crazy.