When Beulah realises that Kellie has feelings for Drew, she tries to derail the wedding to Lily.

Drew decides to propose to Lily.

Lily moves in with Drew, but this proves to be dangerous.

After Oswald and Lewis advertise Drew on Buzz Beer bottles, he meets a woman named Lily and makes a big decision.

Drew starts dating a doctor during a prank war with Lewis and Oswald.

Drew starts volunteering with Speedy at the local hospital.

Drew is given a Rolls Royce as a Christmas bonus.

Drew and Kellie go and stay in a fancy condo to celebrate Kellie's birthday, while Oswald and Lewis stay at Drew's.

Drew starts dating the lesbian daughter of his old Minister, before meeting a bisexual woman at a wedding.

The gang takes part in a karaoke contest.

When Drew realises how little money he makes compared to his co-workers, he decides to take a computer course over the summer. 

Drew resorts to drastic measures to lose weight for a singles mixer.

Drew has to do an ad for the store on Superbowl Sunday.

After Oswald fails his nursing exam, Drew gets him a job at the Neverending Store.

Kellie's ex-husband moves in with Drew while he recovers from an accident.

Drew takes Salsa lessons to prepare for his wedding, which stirs up feelings between him and Kellie.

When Drew's bosses fire the other Internal Expediting Analyst and require him to do his job, he hires a high school girl to help him out.

Drew breaks things off with Robin to start something with Dawn.

Drew runs into Larry at a wedding and Larry offers to set him up as he is now a successful matchmaker.

Drew's mother sets him up with a beautiful woman. There's only one problem.

Drew asks Kelly to accompany him on a double date to keep an eye on him.

The guys try to include Kelly in their group, with mixed results.

Drew is plagued by nightmares of Kate's wedding.

Drew tries everything he can to prevent Kate's wedding.

Drew, Lewis and Oswald meet a girl they used used to go to high school with and Drew invites her to move in. Nicki struggles with this adjustment. Meanwhile, Kate has some important news to announce. Winfred-Lauder has become an online store but Drew manages to secure a job when he decides he no longer wants to be a doormat.