Joe brings a guy to the island whom he hopes will invest in Sandpiper so that Joe can expand the business. But when the guy sees Helen, he asks Joe to fix them up. Joe asks Helen to go out with him and she reluctantly does. It's after that Joe realizes that he used Helen and tries to get her out of it but she's fallen for him.

Davis comes to the island and brings Helen out and invites Joe, Brian, and Alex to come along. They go back to his hotel room and while he goes to freshen up, Helen goes through his luggage and finds a present which she assumes is for her and sees it's something extremely personal. When he tells her that he has something for her, it's not what she saw. So she wonders if he's seeing someone else.

Davis cancels yet another date, so Helen decides to go out with another man. When Joe's date with Sandra suddenly comes into conflict with his date with Joy, Joe decides to lie his way out of his date with Sandra. Joe's lies come back to bite him, as Joy cancels on him. Davis shows up on the island after all, only to find out Helen is out with another man. So he treats Joe to a night out at the Club Car, where Helen and her date show up, followed quickly by Sandra. Joe ends up busted while Davis and Helen go elsewhere to reconcile.

Davis proposes to Helen and she accepts, re-igniting old feelings between her and Joe.

Brian creates a videotape wedding gift for Joe and Helen, including all the times they spent together.

Helen learns that her ex boyfriend Davis has been detained in Asia for over a year and is now on his way back to see her. She then tells Joe to go to Boston to get something. The guys are wondering what's up with Helen. She tells them that she didn't break up with him when she accepted Joe's proposal. She tells them that on the night she was going to see Davis, Joe proposed to her and she accepted. She told Joe that she has to see him alone but when she sees him, he surprises her with a surprise engagement party. And before she could tell Davis she accepted Joe's proposal he left for Asia. When he arrives she finds it difficult to tell him that she married Joe. And when Joe comes back the guys keep him from seeing Helen with Davis.