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Sep 9, 2002-Aug 27, 2003
26 episodes
- Drew's mother concludes Kellie is the one who truly loves her son, not the bride.
- Drew gets an unexpected answer to his proposal.
- Drew's new girlfriend's sleeping disorder makes him want to scream.
- Drew organizes a road trip to meet a girl who responded to an ad Lewis and Oswald placed.
- Lewis and Oswald seek revenge when Drew gives away the Christmas mugs that they made for him.
- Drew gives his dog, Speedy, to an elderly woman who is at death's door.
- Drew gives a used Rolls Royce he received as a bonus to Lewis.
- Drew and Kellie pretend to be married in order to spend the weekend at a mountain condominium.
- Drew falls for a bisexual woman who is also dating his old friend Elaine.
- Drew and the gang enter a big karaoke contest.
- Drew takes a summer course in computers to try to get ahead at work.
- Drew goes on a crash diet to get into an upcoming singles mixer.
- Drew tries to overcome his stage fright and do a commercial during the Super Bowl.
- After Oswald fails his nursing exam, Drew gets him a job in the mail room of Neverendingstore.com.
- Kellie's ex-husband absorbs her attention just as Drew is ready to reveal his feelings.
- Drew finds himself attracted to his dance teacher, then realizes his true feelings for Kellie.
- Drew must hire a computer-savvy teen (Lacey Chabert) to teach him how to do his job.
- Drew falls for a beautiful woman but must contend with her ex-boyfriends.
- A matchmaker (Ian Gomez) finds Drew a prospective mate (Lori Loughlin), but Drew cannot commit.
- Steve asks Drew for help in hiding his affair with a hairdresser (Jeanetta Arnette).
- Drew's mother (Marion Ross) fixes him up with "the perfect girl."
- Drew asks Kate to double-date with him while he searches for a bride.
- Trying to fit in with the guys, Kellie steals a life-size cut-out of baseball player Jim Thome.
- Drew has recurring nightmares about Kate's wedding; Lewis asks Nicki out on a date.
- Drew resorts to desperate measures to prevent Kate from marrying a fighter pilot (Cameron Mathison).
- Unemployed Drew tries to make ends meet, while Nicki continues to mooch off him.