Clutch features numerous types of handbags that the designer Caroline Johnson creates. It is the name of her designer handbag company, she started after graduating Harvard MBA program. During her graduate program, she meets Mike Barnsworth or as his family calls him Michael Fredrick Barnsworth the Third, whose family owns the largest brokerage firm in New York–Barnsworth Brokerage Firm. Mike doesn’t want to follow in his father or grandfather’s footsteps instead Mike wants to own a bar–just like in the move Cocktail that he used to watch with his favorite nanny.
Each chapter is a different type of handbag–backpack, messenger, doctor bag, diaper bag, briefcase, wallet, cosmetic bag, and clutch. Each type of bag represents the various men that Caroline is dating. Through all the types of bags, men, and business meetings, Caroline and Mike maintain their friendship. Caroline goes to Mike’s bar on a regular basis even bringing her dates to the bar for Mike’s opinion of the men. While Mike is a love ’em and leave ’em mode especially with the women in his bar. Caroline doesn’t understand why one of the waitresses that Mike has “dated” refuses to be friendly with her until the head bartender informs Caroline that the waitress thinks that Mike is in love with Caroline that why none of the women have a chance with him. Will Caroline see how Mike really feels?