George is so desperate to get Ted and Casey married that he turns to Leo for help. Minutes before vows are to be exchanged, Casey's mother decides to tell her the real story behind her brief marriage to Leo, which so discourages Casey she goes running from the altar. George, who is even ready to accept a roller-blading priest to get the deed done, has to turn to Leo, a one-man fidelity wrecking crew, to set things straight.

In order to prove to Ted and Casey that he'll be a good grandfather and help out financially when their baby is born, Leo ""borrows"" some of George's things and takes them to a pawn shop. When this scheme doesn't work, Leo lands a job in the restaurant industry - working a drive-through window dressed as a crustacean. Meanwhile, the islanders misinterpret the live-in relationship between George and Leo, but their open-mindedness helps Bob sell more books. An angry George kicks Leo out after catching him pawning items from the bookstore, but when he discovers that Leo was putting the money towards a trust fund for the baby, he relents and tracks him down to apologize.

Ted and Casey hire a nanny to care for their new baby, Alice, who seems to be the perfect person to care for the new baby. She's a registered pediatric nurse, warm, smart and loving. The problem is she's a little too loving when it comes to Ted. When Alice, mortified by her crush, decides to quit, it's up to George to figure out a way to keep her on the island and away from Ted.

Leo talks George into visiting his new love Tasha, a massage therapist, but Leo fumes when he's convinced that their session turned out to be more than professional. (Part one of two)