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.

In a flash-back, after being jilted by Mira, Malcolm & Eddie meet each other for the first time at Eddie's wedding. Malcolm consoles a jilted Eddie after his bride-to-be left him standing at the altar, by relating his own disastrous trip to the altar.

Business partners Malcolm and Eddie open a jazz club with Malcolm's money. And after Malcolm throws it up in Eddie's face and wants to make all the decisions, Eddie looks for ways to raise his share of the money.

Malcolm and Eddie each meet the girl of their dreams. Malcolm's girl is sweet & demure and likes to cook for him. Eddie's girl is a ""straight-up hood-rat"" that likes to drink 40 ounce bottles of beer. The men eventually find out that their dream girls are one and the same, as she is someone who takes the concept of ""I'm Every Woman"" to the extreme.

Malcolm's estranged brother comes to town, igniting old tensions, but reviving old family ties. Meanwhile, Nicolette takes a job in a bowling alley, and tries to get along with unruly customers.

Nicolette stays with Malcolm & Eddie while her place is being painted and her quirks & habits drive the guys crazy.

Its Nicolette's 30th birthday, and the gang decides to have a surprise birthday celebration for her. But the thought of turning 30 without ever having had a baby is too much for her to handle. So Nicolette asks Malcolm to father a child for her, and to do it via artificial insemination.

Eddie seeks justice on a televised court show ""Citizen's Court"" after Malcolm allows his hats to be stolen from his car, while taking them to the cleaners. Malcolm had left the windows down and the car unlocked.

Malcolm and Eddie receive tickets and all expense paid trip to New York to appear on a panel for a sports fanatic show, on the Jerry Stein show. So the guys show up for the taping dressed in weird sports-fan attire, but are unaware that they are actually on a talk show about devil worshipers. They can't understand why the audience is jeering and booing them, until the rest of the panelists come out on the stage.

The Fifty/Fifty Club is ransacked after the guys refuse to pay protection money.

Nicolette prompts the guys to offer a ladies night, including male strippers.

A contractor (Coolio) consults Malcolm and Eddie about building a club in Chicago.

The staff of the Fifty-Fifty club goes on strike and Malcolm and Eddie refuse to budge on their labor negotiations. But chaos soon ensues in the club, forcing the guys to give in to their worker's demands.

As the profits from the 50/50 club begin to grow larger and larger, Malcolm and Eddie clash over whose money-making strategy is best. Malcolm believes in investing his money in the stock market, while Eddie believes in betting on horse races.

A gorgeous bandleader (Cindy Herron) breaks up Malcolm and Ashley.

Ashley catches Malcolm kissing Olivia. After their breakup, Malcolm goes into a funk and Eddie goes to extraordinary lengths (and heights) to pull him out of it. Eddie tries taking Malcolm on a hot-air balloon ride.

The duo agrees to listen to a realty sales pitch in order to get a free seven-day cruise.

Dexter returns and asks Eddie for another loan—it seems he's been evicted from his apartment yet again. Heeding Malcolm's advice, Eddie doesn't give him the loan but takes a stand to help Dexter back on his feet. However, the situation changes once Dexter gets coffee spilled on his lap at the club.

The guys deal with a new rival for their business, a beautiful buxom woman who opens a dance club down the street from the Fifty-Fifty Club, by holding a bogus contest to attract new customers. The trouble comes when the guys decide to fight fire with fire, and rig a bogus contest of their own, but with disastrous results.