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.

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.

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.