After being told by Lydia (Krista Allen) and Jimmy (Nathaniel Buzolic) that he needs to loosen up, Nate (Josh Zuckerman) 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 (guest star Mircea Monroe). Elsewhere, Sam (guest star Emma Fitzpatrick) struggles to write the lyrics to her next song after Atticus (guest star Jay Ali) 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.
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