Mystery writer Ben Coleman develops writer's block after falling for a woman--a fictional character in his latest detective story. He briefly bumps into caterer Laura Kelly at the supermarket, and becomes convinced that she is the fantasy woman he had conjured up in his story. The two finally meet formally at a wedding (she is catering the affair for the groom--her ex-boyfriend; he was dragged there as a favor to his best friend Richard), and immediately hit it off.

During the reception, Ben sends the busy Laura a romantic poem written on a napkin, and then joins her in the kitchen. They share a dance at the end of the evening. A few days later, Ben calls and sets up a date, thrilling both Laura and her overly enthusiastic sister Jane. Richard--who has forgotten his anniversary--pleads with Ben to double-date with him and his fuming wife, Linda, in the hopes that the other couple's presence will cause her to show some restraint. Richard and Linda wind up getting into a screaming match in the restaurant and later make up (and make out) in the car in front of a bewildered Ben and Laura. Ben later calls Laura, and they are able to salvage the evening by continuing their date over the phone.

Ben and Laura spend three hours talking on the phone before finally saying good-night. Ben is so ecstatic that he races over to Laura's apartment the next morning with gifts. Laura find this a bit off-putting, and is disgusted to learn that he called her ex-boyfriend Kevin to get tips on Laura's likes and dislikes. She wants nothing to do with Ben, but Jane tries to convince her to give him another chance. Ben apologizes, and they decide to begin dating. Laura wants to take things slow, but they wind up going out every night for a week. Laura fears that she will lose her independence and tells Ben that she wants to back off for a while. Both are left lonely and miserable, and Ben drives Richard and Linda crazy as he spends all of his time with them. Laura comes over to tell Ben that she has changed her mind, and they share a kiss.

A beautiful ""old friend"" of Ben's comes to town and wants to stay at his place.

Linda goes into labor and freaks out once she's at the hospital.

The guys blame Richard's terrible play for their lack of success on the softball field, and pressure manager Ben to ask him to leave the team. Ben cannot bring himself to do this because softball seems to mean so much to his friend. The other players also fail in their attempt to give Richard the boot (because he feeds them seafood), and the team continues to rack up losses. After an especially embarrassing outing, Richard realizes that he is a horrible player and offers to leave. The team's fortunes don't improve after Richard's departure, so the guys ask him to come back. Meanwhile, a bemused Linda tries to fulfill Amanda's request that she sing to her.

Linda's wheelchair-bound sister comes to town to collect a Woman of the Year Award, but she decides to decline after helplessly witnessing a mugging.