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.

George goes to war when a bookstore chain sets up shop on the island, offering 10,000 titles, CD-listening booths and cappuccino, and the owner vows to put George out of business. When Pendragon's, the flashy new bookstore with cappuccino and CDs, opens on Martha's Vineyard, George isn't worried about the competition. That's until Pendragon's manager May informs him that she's planning to run him out of town, which forces him to activate his secret weapon — Leo, and all his boyish charm.

While he is reminiscing about Casey's childhood on the eve of her baby shower, Leo remembers that he convinced his old friend Robert Goulet to sing her a song on her seventh birthday. Eager to make a big splash at the shower, Leo tries to get Goulet, who is making a guest appearance at George's bookstore, to sing for Casey again. Unfortunately, this time, the song produces more than just applause.