David and Skye ponder their respective futures, both romantic and professional, as they spend an evening in New York City. Wheeler and Misty spend the night driving around town and discussing life.

Skye talks David into joining an uncomfortable Father's Day brunch with a less than thrilled Getty. Sam wants to celebrate with some father and son time of his own. Nash sets his romantic sights on a wealthy widowed club member, and Wheeler launches a new moneymaking scheme.