Jimmy starts his new career as a full-fledge building contractor. His first client: game show host Alex Trebek. With the help of his architect partner, Jimmy learns that there is a special way of dealing with celebrity clientel. Jimmy also coaches Gene in the art of making moves on women. It seems Gene has it together when it comes to approaching people in the Jaguar showroom where he works, but with women, he hasn't got a clue. However, after selling a beautiful woman a new car, Gene musters up the courage to ask her out. Meanwhile, Wendy gets a dog from the pound that is anything but a ""standard"" poodle.

Jimmy and Donna are in a continual amorous mood and at every turn, someone manages to walk in on them while they're ""getting close."" Afraid they've scarred Wendy for good from this experience, they attempt to broach the subject of the birds and the bees but realize that she's still too young to even care to hear it. Jimmy makes his first appearance on-site as the building contractor at Alex Trebek's house. It seems our celebrity client has some pretty outrageous ideas for his home and it's up to Jimmy and Sabrina, his architect, to try and make them happen. A woman named Mel Hanlon, who used to live in what is now Jimmy and Donna's house and who also happens to be an ex-therapist, arrives on Donna's doorstep in the hopes of taking a nostalgic look at her old home. A friendship strikes up between the two and it appears we may see Mel more in the future.

Having not had a sit down dinner with the entire family in quite a long while has gotten to both Donna and Jimmy. They decide to set up a new rule, which is that the family will start eating dinner together more often. No more nights out with friends, no more excuses for having other things to do. However, one thing after another keeps this from happening and the evening keeps getting pushed back.

Jimmy is crushed when Bonnie decides to break up with Mitchell after developing a crush on the hunky guy who delivers their water. Meanwhile, despite Jimmy's advice, Gene continues to stalk Terry.

The adults attend a speed-dating session, including Donna and Jimmy, who are trying to gauge their appeal at middle age.

Jimmy and Donna learn that Bonnie, despite failing her driver's test three times, has been borrowing their car at night; Wendy finds out she was born out of wedlock.

Jimmy fears that Chester will grow up to be gay because of all the females in the house; Gene learns Terry still isn't over Elliott.