After being told by Lydia and Jimmy that he needs to loosen up, Nate reluctantly agrees to go on a series of dates with women they meet on a dating website. Quickly realizing that speed dating isn't for him, Nate throws in the towel, but Lydia urges him to go on one more date with a girl named Annie. Elsewhere, Sam struggles to write the lyrics to her next song after Atticus points out all of her songs are about Nate. Finally, when Jimmy makes a surprising discovery about Annie, he and Lydia disagree on how to break the news to a smitten Nate.