Eddie's luck seems to take a turn for the worse, each time Malcolm's luck takes a turn for the better, leaving Eddie battered & beaten. Malcolm meets a girl who he believes is the ""perfect"" girl, until Eddie tells him that he's already Been there, Done that! Meanwhile, Nicollette is exuberant about taking the exam for the Police Academy.

Malcolm's banker convinces him to hire his arsonist daughter as a waitress in order to have his loan for a new roof approved. Meanwhile Eddie sweet-talks Nicolette into continuing their secret love affair, in order to keep things spicy.

When their customers opt to go to a competing bar down the block, Malcolm decides to turn McGee's into a gambling establishment and save himself from bankruptcy.

Malcolm, his gay sister, and Eddie compete for the attentions of a new waitress.

Nicolette wants to make her relationship with Eddie a public one, while Eddie continues to want them to meet in secret. Nicolette is asked to the policemen's ball by another man, and feeling rejected by Eddie, she decides to go. Eddie gets jealous and tries to stand up for his woman, but he falls far short. Malcolm unwittingly buys stolen lobsters for the club's catering of the policemen's ball, and Simone does a fantastic job of making them a hit.

The guys may become family when Eddie's mother starts dating Malcolm's father.

After Malcolm and Eddie each make suggestions to the other about ways to improve each other's business, they decide to make a bet, which leads the guys to switch places and run each other's business for a week.

Simone tries to win Malcolm's heart through his stomach with some special chocolate cookies, but once Malcolm tastes them, he only wants to use them to go into the cookie business with. Meanwhile, McGinley tries to lure Simone away from Malcolm, to work in his bar.

Malcolm inadvertently places a large bet on Eddie when he competes in a NASCAR race. Nicollette fears a dream she had about Eddie might come true.

Eddie subs as coach of a peewee basketball team in order to show up a rival, and Malcolm worries that his trash-talk tactics will leave the team in the dumper.

The guys discover that baby-sitting Eddie's infant cousin draws women, but then they panic when they realize that the baby is missing.

Friends guide feuding Malcolm and Eddie down memory lane.

Malcolm acts as chef Simone's husband to fool her high-school nemesis.

Malcolm dreams about a distant future where he and Eddie are still roommates.

Malcolm uses tough love on his sister who gets fired and dumped in the same week.

Nicolette enlists Malcolm and Eddie to help her shy beau find the words to propose. So the guys devise a plan to help Stanley gain some confidence by encouraging him to become a lady's man. As his confidence grows, the plan begins to backfire, with disastrous results for Nicollette.

It comes as a shock to Malcolm and Eddie when they learn that their old pal, Nelson Carter, is getting married. After all, there was a better chance for the Pope to get married before Nelson ever decided to settle down. But on the day of Nelson's wedding—and after a wild night at his bachelor party—the two begin considering settling down themselves.

Malcolm, his sister Maura, Eddie and his mother Sheila are preparing a surprise party for Malcolm's father Marcus. Maura and Sheila start arguing over what they believe to be Marcus' favorite cake, but things really start heating up when Eddie's Grandpa, Aunt Ruby, Uncle Lud and Cousin Doyle make an unexpected entrance.

Everybody thinks Eddie's pal Rusty is crazy. During his career as a NASCAR driver, Rusty had one too many racing accidents that have left him short of a few lug nuts. His presence at Eddie's garage and Malcolm's bar has been good for business, though. However, Nicolette discovers that Rusty is really an alias and that he's a lot crazier than anybody originally thought....

Malcolm's dream to renovate McGee's into 1930s jazz club is in full swing when he discovers that the contractor he hired to build his bar turns out to be an old Navy buddy of Eddie's. Since he and Eddie did not get along in the Navy, the contractor leaves the job until Eddie gives him an apology, leaving Malcolm without a bar.

Needing Tim's help in getting a tattoo removed, Malcolm agrees to date Tim's feisty sister & really turns on the charm to soften her stoney heart. But Tim may not be too happy about the results. He threatens Malcolm that he should not hurt his little sister, or else! Now Malcolm must find a way out of this relationship, but he must be extremely careful.

Malcolm's life changes after meeting a spiritual counselor, falls in love with her, and decides to sell his bar. His wedding plans dissolve after she decides she's really in love with someone else. Meanwhile, Eddie decides to take an executive job in Pittsburgh.