Oswald fails the Nurse exam again and needs a job. One has opened up at Drew's work but Drew doesn't think Oswald can do the job. When Oswald is offended Drew gets him the job and Oswald trains well. Mimi vs Traylor fighting escalates.
Drew's bosses ask him to do a live commercial for the website during the Super Bowl broadcast, which results in a disgusting mishap that is aired worldwide.
Matchmaker Larry holds a "no fatties allowed" mixer so Drew can't go, so he starts a drastic fast to lose enough weight and starts having weird hallucinations.
After the gang buys a trip to Florida, Drew decides he needs to attend a computer-programming class to earn better money. He changes his mind and tells his bosses his grandma died so he can go, but then he's sick the whole time.
At karaoke night at the Warsaw, Kellie tries to sing but needs Drew's help. They are told of a karaoke contest with $1,000 and an Olympic gold medal for winning. Drew and Kellie prepare to compete but for some reason Drew pushes too hard.
Drew bumps into his former pastor and his daughter Elaine at the Warsaw. Drew asks her out and she accepts. Drew finds out she's gay and she reveals she wants him to play along to quiet her parents. Then they start vying for the same woman.
Kellie says her "birthday is next week and I have nothing to be happy about." Lewis and Oswald have termites and give Drew an invitation to a mountain condo so they can stay at his house. At the condo when staff hits on Kellie, trouble.
Evan gives Drew an old rundown Rolls Royce, but Drew can't afford to restore it so he gives it to Lewis. But Lewis goes power-mad and thinks himself above the "mortals," so Drew must somehow take back the Rolls.
Drew gives away his dog to a dying, elderly woman that has less than a month to live as a nice gesture to impress the woman's granddaughter, then regrets it.
When Drew throws out some mugs given to him by Lewis and Oswald, it sets off a prank war that includes moved furniture, painted bar stools and ends in an unneeded colonoscopy, which costs Drew a shot with his new doctor.
Oswald and Lewis put Drew's picture and number on Buzz beer bottles to get a wife. A bottle ends up in New Orleans with a woman with whom Drew has an immediate connection. Road trip.