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.

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.