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Jack is worried because his marraige to Carly is entering the ""red zone,"" the fourteen-month mark around which her other two marriages began to fall apart. At this inopportune time Gail, a woman who Jack once had a short, scary relationship with, shows up. Gail announces she's getting married and wants back a watch of hers that Jack kept when he fled from her. Jack tries to get the watch back from Will, to whom he gave it as a gift, but Will gave it to his father Dante. Trying to hide it all from Carly, Jack folows the torturous route the watch has taken from a pawn shop to Stephanie to Sheldon to Sarah. When he finally gets his hands on it, both Carly and Gail see it, too.