Jimmy meets Gretchen's parents, against her wishes. Gretchen breaks up with Jimmy, after she had secretly found an engagement ring she believed was for her.
When Gretchen's parents pay her a visit, she attempts to conceal them from Jimmy, first by pretending to leave town to see them, and then by persuading a random couple at an art exhibit to pose as them. She concocts an elaborate lie about them having to return home so her father can have a back operation.
After she leaves Jimmy realizes, in a sequence parodying The Usual Suspects, that she used cues visible in the gallery to invent the lie.
Lindsay, guilty over having cheated on Paul, spends a day with him. Edgar attempts to get medication from the VA office to help him sleep, but finds the caseworker is trying to avoid helping him.
Following Gretchen to an expensive country club, Jimmy is shocked to learn that she had a strict upbringing and her parents still think she is a goody-two-shoes.
Jimmy "outs" Gretchen to her parents, causing a fight with Gretchen at Jimmy's house. Sneaking into Jimmy's room, Gretchen accidentally finds the ring Jimmy originally bought for Becca. Thinking it is for her, she announces she is done with Jimmy and runs out.