When Helen has another audition and is not chosen; Brian points out that she dresses too conservatively and that she should consider sexing it up a little. Meanwhile, Fay is attracted to a man who has been traveling around the world and is on the last leg of his journey. When Fay asks him why doesn't he complete it, he claims that if he does he will die.
A pilot who knows Brian has a layover at Nantucket and tells him that his ex-wife, Carol, is moving to London. Brian learns that she'll have a layover in Boston so sends her a message asking her to meet him. When Joe learns of this he tells Brian she won't be there. But Brian decides to go even with a fog covering the island. Joe and Helen decide to follow him.
Brian asks a girl out and she agrees on the condition that he find someone for her friend Cindy. And he volunteers Joe. Joe initially refuses but Brian guilts him into it. Later he learns that Cindy is very "popular", which makes him reconsider, but then Helen guilts him. And at their date one of her exes shows up and when he treats her crudely Joe stands up for her.