Kate's mother takes Kate, Drew and Lisa out to dinner to celebrate Kate's birthday. Kate does not tell her that she is seeing someone because her mother never approves of any of her boyfriends. Kate has led Jay to believe that her mother is in an institution. Lewis inadvertently tells him the truth, so Kate has to invite Jay to have dinner at her mother's house. 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. They 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, and suggests that they mi