Drew and Kate and Kate's Mom was the 20th episode in Season 1 of The Drew Carey Show, also the 20th series episode overall. Originally aired on February 27, 1996 on ABC-TV, the episode, was directed by Brian K. Roberts, and was written by Jeff Lowell.
Kate tries to conceal from her mom that she is dating Jay, since she is always disapproving of her boyfriends. But when the truth comes out, she has to make up by inviting Jay over for dinner at her mom's house. Just as Kate suspected, her mom worries Jay is on the rebound and tries to convince Kate that Drew is the right man for her.
Kate's mother Lynn (Susan Saint James, in guest appearance) takes Kate, Drew and Lisa (Katy Selverstone) all out to dinner to celebrate Kate's birthday. Kate does not tell her mother that she's seeing someone, because her mother never approves of any of her boyfriends.
Mrs. O'Brien learns of Jay's recent divorce, and worries that he is on the rebound. She fears that Jay will hurt Kate, and asks Drew to try to convince Kate to stop seeing him. Kate panics when Jay has to break a date because of work, and pressures him about the future of their relationship.
Jay and Kate wind up breaking up. Kate confronts her mother, who insists that she has been overlooking the perfect man: Drew. Kate is incredulous. The gang gets drunk at the Warsaw in an attempt to cheer up Kate. Drew and Kate ride around in a cab talking until the car gets a flat tire. Kate tries to kiss Drew, as she tells him what her mother suggested in the two of them possibly dating, as he's flattered, but dissuades her of the idea, as he refuses to take advantage of her as well.
Later, at work, Drew calls Kate to his desk, as moments later, Lynn and Jay walk in to invite Drew to lunch, as they also reveal that they had been talking about the crazy way Kate had been acting, as Jay told Lynn that he loved Kate, and reveals that Drew got he and Kate's mom to talk, as Kate and Jay reconcile.