Trouty, Kenny’s friend, joins the poker game. The guys don’t like Trouty and think he’s a bad hang. Meanwhile, PJ tries to get the guys to hang out with Hank. In return, PJ agrees to spend some time with Wendy.

When PJ tells the guys that she and Brendan made out back in college, things start to get weird between them. Meredith wants to throw Andy a surprise birthday party and asks PJ to keep him busy the day of so she can prepare. PJ and the gang surprise him when they take him to Wrigley Field. PJ realizes the horror stories Andy has been telling about Meredith aren’t true. And Brendan admits that he had feelings for PJ back in college. They sort things out and then he surprises her with a kiss.

The kiss that ended last episode seems to not have had any lasting effect as Brendon has moved on to another girlfriend. Kenny also has a new girlfriend who happens to have a bun in the oven. And Andy is getting used to live in the suburbs, including the long commute that comes with it.

Brandon is chosen as one of Chicago’s Top 50 Sexiest Bachelors while PJ contemplates an ethically questionable relationship with the new Cubs pitcher. And Trouty makes an appearance in an unexpected place.

Bobby's brother, Jack, shows up for Bobby's party and takes and interest in P.J. Stephanie meets a man named Warren at a bar and they strike up an informative conversation.

Tension between Jack and Bobby threatens the gang's weekend at a luxurious ranch; Mike connects with an older woman (Mimi Rogers); Kenny gets fashion advice.