Drew is an assistant director of personnel in a Cleveland department store and he has been stuck there for ten years. Other than fighting with co-worker Mimi, his hobbies include drinking beer and not being able to get dates. To make a few extra bucks he has a micro-brewery going in his garage with his buddies.
Drew and Oswald get a little too competitive as they try to set up their mothers with an attractive eligible widower.
After learning that Gus's soccer team is in a league that has set things up to make sure that no one ever loses (to keep the kids from feeling bad), Drew tries to butt in, leading to disastrous results for his nephew. Lewis and Oswald make the mistake of getting involved with Kellie's cousin, who turns out to be a kleptomaniac.
After Evan leaves for a yoga retreat, Traylor begins a romance with Scott as part of a power play to seize control of the office. She puts an end to the laid-back work environment; and worst of all, takes away the foosball table! Meanwhile, Lewis gets involved with the Warsaw's new cook.
Drew is thrilled when he and Kellie decide to exchange keys. However, he nearly thwarts the progress in their relationship when he ends up letting Scott use Kellie's place to cheat on Traylor.
Drew hopes to make a commitment to Kellie after they learn that she is pregnant. However, she is unsure if this is the right decision. Drew seeks her parents' help to change her mind, only to find that they are not exactly thrilled with the idea of having him as their son-in-law.
While taking a pregnancy quiz with Kellie, Drew recalls his father's death in a fall from the roof. Drew was horrified to discover that he was never even mentioned in his dad's diary, and tried to prove himself by arranging for a lavish military-style funeral. However, disaster struck when George accidentally wound up with a casket featuring the logo for the band Kiss.
Kellie is furious with Drew after he blows off an appointment to see their baby's first sonogram to go drinking with the guys.
Kellie's fears about Drew's inability to be a good father grow after Gus suddenly begins misbehaving every time he is around his uncle. Inspired by Mimi's romance with a widower, Oswald and Lewis hope to set themselves for life by picking up wealthy widows.
As a sign of support, Drew pledges to stop drinking for the duration of Kellie's pregnancy, but soon finds it very difficult to keep his promise. Meanwhile, Mimi has the hots for a handsome delivery man; and Oswald becomes part-owner of the Warsaw.
Kellie tries to convince Drew to become friends with a new neighbor, but it all blows up in her face when the man turns out to be a clingy pest who just will not leave Drew alone.
Drew turns to a shady travel agent for help when he is unable to put together the funds to finance Kellie's dream vacation in Italy.
Kellie tries to get Drew and her father to overcome their differences by having them work together to fix up an old house for sale. Mimi turns to Larry's matchmaking service in her quest to find a new man.
Drew tries to make some extra money for the baby by betting on a greyhound that has been enhanced as part of a DrugCo project.
After Tony the bus driver gets into an accident, he pleads with Drew to keep it a secret because he is close to retirement and doesn't want to risk being fired and losing his benefits package. Drew cannot do this because he fears for the passengers' safety, so he tries to convince Scott to give Tony another job.
Drew has trouble getting romantic with Kellie after a photo of the baby puts a lot of very strange ideas in his head.
In the aftermath of his disastrous marriage, Drew heads off alone on his honeymoon to try to define his feelings for Kellie. Oswald and Lewis head to Mexico ahead of Drew, where Oswald accidentally falls for a hooker, unaware of her identity because he doesn't know how to speak Spanish.
Mimi encourages Drew to make friends with the gay parents of Gus's friend. However, Drew winds up inadvertently splitting up the couple and finds himself as the "other man."
Drew resorts to drastic action after Mimi's latest boyfriend moves into the house and begins mooching off of him.
Mimi blames Drew after her house burns down, apparently as the result of a gift given to Gus by his uncle. Oswald starts a change machine business.
The gang tries to teach Gus to lie to an insurance adjuster so that Mimi can receive the claim on her house and be able to replace it.
Drew and Kellie's new relationship is threatened by their strong political differences.
Lewis is depressed due to breaking up with his girlfriend so Drew and Oswald take him to a strip club where he suffers a breast related injury. Drew gets caught lying to his girlfriend about the club when Lewis sues the dancer.
Drew receives a letter from Steve with a check to help since Mimi lives with him. He wants back with Mimi but she is dating Larry so Drew arranges a meeting. Then a one-night stand Steve had in his world travel arrives and Steve tells Mimi.
Drew puts his plan to propose to Kellie on hold when he finds out her parents are getting a divorce.
Drew comes up with a plan to open a retro store, and seeks a partnership with the now-wealthy Wick. However, all of Wick's funds come through his father-in-law, so Drew must help cover up Wick's extra-marital affair or lose his financial backing.
Kellie finally agrees to marry Drew, but their wedding plans are thrown into disarray when she goes into labor.
