Greg and Ellen Sawyer have been married for 19 years. Tess and Monica's assignment is to make sure they stay married well past twenty. Greg, a successful Portland developer, is often to preoccupied with his work to notice Ellen. But when securing a business deal takes precedence over their 20th wedding anniversary celebration, Ellen begins to question her marriage. When Monica, working as Ellen's assistant, helps her go through some old boxes, Ellen discovers love letters from an old boyfriend, a musician named Denny. The passionate letters reawaken Ellen's sense of romance and she begins to wonder if she made a mistake in marrying Greg instead of Denny. Meanwhile, Andrew refuses to sell Greg a lucrative piece of property that would cement Greg's plans for a waterfront condo. In the ensuing negotiations, Greg barely notices when Ellen leaves to celebrate their anniversary alone at their cabin in the woods. Instead of going to the cabin, Ellen detours to Oregon City, in hopes of