Newly unemployed Drew invites an old girlfriend from highschool to stay with him when he finds she needs a place to live, but Nikki doesn't take kindly to her presence. Meanwhile, Kate announces that she is to be married to a guy she met in New York.
With Kate's impending marriage, a desperate Drew uses a plethora of tactics to stop to stop the wedding.
Kate's wedding is causing nightmares for Drew but not as scary as when Lewis take Nikki out on a date.
In an effort to fit in with Drew's friends, Kellie steals a cut-out of local baseball legend, Jim Thorne resulting in legal trouble.
Drew double dates with Kellie so he can have some support while on a quest for his perfect mate while Oswald is wrought with guilt after "defacing" his mother.
Drew's mother attempts to set him up on a date with her notion his ideal woman.
Drew's brother Steve reveals his affair with a hairdresser to Drew and needs his help hiding it from Mimi.
A former co-worker turned matchmaker tries to help Drew find a wife. But despite his success in finding the perfect woman, Drew still isn't interested.
Drews meets a woman on a bus who may be "the one" but he must contend with her dating history and free spirit.
Drew must hire a teenager to teach him how to do his job after the other person who does the mystery job gets fired and Oswald and Lewis let Steve stay with them after he is kicked out by Mimi.
Drew takes salsa lessons and is attracted to his teacher but after practicing his moves with Kellie, new feelings start to brew for her.
As Drew prepares to tell Kellie how he feels about her, she becomes distracted by the sudden arrival of her apologetic ex-husband who was injured in an accident.
When Oswald doesn't pass his nursing exam, Drew takes pity by getting him a job in the mailroom at his company and Drew slowly realizes why Oswald has trouble finding a job.
Drew's stage fright interferes with a chance to be the star of his company's Super Bowl commercial.
Drew goes on a crash diet to get into one of Larry's singles mixers, but his food depravation causes him to hallucinate.
To try to get ahead at work, Drew takes a summer course in computers.
The gang enters a big karaoke contest and Drew drives Kellie crazy when he teams with her for the competition.
Drew falls for a bisexual woman who is also dating his friend, Elaine. When complications arise, the woman suggests a solution - a threesome.
After Drew buys an engagement ring for his unknown future bride, he has no money for Kellie's birthday, so, pretending to be husband and wife, Drew and Kellie go for a free weekend in a mountain condo
After Drew gives Lewis a used Rolls Royce, Lewis thinks he's too good to hang out with the gang.
Drew gives his dog, Speedy, to an old woman who is at death's door.
Lewis and Oswald plot revenge when they discover that Drew gave the Christmas mugs they made him to the Salvation Army.
A woman responds to an ad that Oswald and Lewis put on Buzz Beer bottles with Drew's picture and phone number, so Drew and the gang go on a road trip to meet her.
Drew has to cope with his new girlfriend's disorder - screaming and flailing in her sleep.
Drew proposes to Lily. Also, Mimi sets Kellie up with the headmaster of an exclusive school.
As Drew and Lily's wedding approaches, Drew's mother realizes that Kellie is the woman who really loves her son.