Naive 20-something Josh Greenberg is in search of love. Things aren't exactly in his favor to find his ideal mate -- for he has a bad job and apartment and is afraid to approach women. But his best-friend/confidant Mike -- his polar opposite -- is a cool, confident bro with an expense account. Mike is also the proverbial devil on his buddy's shoulder, pushing him to engage in activities like sex and drugs. Also in Josh's life is his sister Liz, a corporate lawyer who wants him to get his act together. When Josh does finally find love, he tackles his toughest challenge to date: a serious, long-term relationship and all that comes with it, including anniversaries, merging friend groups, and learning to live their lives as a team.