I'm With Lucy is a 2002 romantic comedy starring Monica Potter in the title role, with Henry Thomas, David Boreanaz, Anthony LaPaglia, Harold Ramis, Julie Christie and John Hannah.
Lucy is a journalist who is dumped by her "perfect" boyfriend and then goes on a series of dates with five different men - Doug, an entomologist; Gabriel, a playwright; Bobby, a baseball player; Barry, a computer store owner; and Luke, a doctor. She acts differently around each of the men - she is drunk on her date with Doug; she uncharacteristically jumps into bed with Gabriel; she is, at first, irritated with but then moved by ex-baseball star Bobby; her date with Barry gets off to a rough start, but then while on their date, they run into her parents and end up having dinner with them; and her date with Luke is sidetracked when they see a colleague of Luke's who is with his daughter, Eve, who appears to have her own eye on Luke.
She doesn't connect with Doug, but she does get him to come out of his shell by the end of the date. She takes Bobby to several places that put him completely out of his element and then he takes her to a baseball card show where she discovers a different side of him. Her date with Gabriel essentially becomes a one night stand when she realizes he isn't what she wants in life. She becomes serious with Luke, but an incident at a restaurant in which he is rude to one of the waiters makes her realize he isn't the one she wants, either. Barry surprises her several times throughout the movie with touching and thoughtful gestures, which of course win her over in the end.