Lydia and Jimmy have been spending a lot of time binge watching TV together but have not gone out on a date. Nate thinks this means they aren’t sure that this relationship is going to last. Lydia insists that that isn’t the case. When Jimmy asks if she really wants to go out on a real date, she says yes.
Jimmy panics. He normally doesn’t date but rather keeps things casual and he wants to make Lydia happy. He asks Nate for advice. Nate suggests wine tasting and a fancy dinner but Jimmy can’t afford that. Nate is too uncomfortable to give him any further advice. Later, Jimmy goes to Atticus for advice but things just get weird. Instead, Jimmy agrees to do farm work to earn money in order to afford the date that Nate recommended.
Jimmy calls Nate out on not having sex with anyone over the last year, which just happens to coincide with when Sam began working at the restaurant. Nate claims he can hook up with someone at anytime but strikes out with the young woman at his restaurant. Then he catches the eye of Pepper, a cougar (played by Denise Richards) and the two plan to go out.
Nate and Pepper run into Lydia and Jimmy at the winery for their wine tasting. Jimmy’s reservation is actually for tomorrow night and there are no openings tonight so the four of them decide to share a table. It turns out that Pepper and Lydia have known one another for years but when Pepper starts making sexual comments about Nate, and infers that Lydia is only playing games with Jimmy, Lydia gets upset and calls off this evening out.
Nate decides that hooking up with Pepper isn’t something he really wants to do. Pepper ends up hooking up with Dylan, the young hot host. When Lydia explains why Pepper’s comments about Jimmy upset her, Jimmy has no trouble defining their relationship; he considers Lydia his girlfriend.
Back at the restaurant, Nate runs into his father. When Nate once again claims not to be in love with Sam, Harrison remarks that Nate isn’t in love with Sam the same way he isn’t still in love with Lydia. Sometimes the worst lies are the ones we tell ourselves.