After losing his roommate to marriage, ladies man Danny goes on the hunt for a replacement and ends up at a bar called Black Eyes listening to the owner, Justin, sing to himself with his headphones on. They have a natural rapport and become fast friends even though Justin's not as confident with women as Danny - exemplified by the ease with which Danny hits on Nicki, the beautiful bartender Justin has a crush on. In fact, Danny's moves impress the entire gang at the bar - Burski, Shelly and Brett - none of whom manage to score conversations let alone dates with prospective females (or in Brett's case, males).
Danny's quick to offer mentoring skills to his new roommate, which Justin rejects until he makes a total fool of himself trying to hit on Nicki. This sends Danny into action, and he invites all the guys to an event organized by his sister, Leslie, a wine representative. He attempts to correct their awkwardness as they approach other singles, but the big shocker comes the next morning when he learns Justin got lucky... with Leslie! Danny flips out and confronts her, only to discover they didn't sleep together at all.
Back at Black Eyes, Danny bursts in, angry at Justin for not sleeping with his sister. The two argue, exhibiting fundamental differences of opinion that appear to end their brief stint as roommates. But after Danny leaves, Burski, Shelly and Brett make a genuine appeal to Justin - they think Danny could be helpful to all of them. Justin eventually agrees, and when he returns to the apartment, he and Danny make amends, with Danny admitting he needs a friend just as much as Justin needs a dating coach.