 When Sam goes away on vacation, he chooses Woody to hold down the fort at the bar. Woody is prepared to do so, but unprepared for the Dear John letter he receives from Beth. Wanting to explain in person, Beth and her fiancé, Leonard Twilley - who Woody knows - plan on stopping in Boston on their way to Niagara Falls. Although Woody is sad, he is more fearful of looking pitiful in Beth s eyes by not having a girl on his arms. Seeing that Beth and Leonard s stopover is a short one, Diane thinks that making up a girlfriend for Woody is not a bad idea. However Beth and Leonard s stopover is a bit longer than either Diane or Woody thought, and Beth suggests that they, including Woody s girlfriend, go out for dinner. As a last resort, Woody picks a name out of Sam s little black book - Desiree Harrison - who, according to Sam "is the best" and has multiple stars next to her name. When Desiree comes to the bar at the appointed time, she is not what Woody expected. She is slightly older and a bit rough around the edges. She is, in fact, Sam s cleaning lady. But it s too late for Woody to back out of a date with Desiree as Beth and Leonard have arrived. After dinner, they return back to the bar. Diane thinks that it best that Woody tell Beth the truth. He does clear the air with her about his true feelings for her and Desiree s true identity. Beth likewise tells Woody that she still loves him but that a long distance relationship just isn t going to work, and she s not prepared to move to Boston just as Woody s not prepared to move back to Indiana. With Beth and Leonard on their way, Woody still has to deal with Desiree. He also clears the air with her. He did have a good time with her and just needs someone with who to talk. Desiree s there for him.