With nowhere left to turn, a worse for wear Claire lands on Loudermilk's couch. Deciding she needs to be taught a lesson, he and Ben take her on their version of a vision quest. Loudermilk also makes a play for his new neighbor, Allison.

Loudermilk goes to great lengths to get Claire to open up about her deep-seated issues, with mixed results. Mugsy reaches out to his estranged daughter and finds that some relationships are harder to fix than others.

Loudermilk is fed up with Claire's couch crashing and wants her gone, but her mother bribes him to continue to keep an eye on her daughter. Roger's conflicted when his old rock band is approached to use their music in a beer commercial.

A new member, Tom, joins the group who isn't all he appears to be. Cutter takes Tom under his wing to make sure his charge stays clean and sober, no matter what it takes. Loudermilk and Allison butt heads over her taste in music.

Cutter continues to make Tom's life a living hell, but no matter what he tries, Tom can't shake him. When he turns to Loudermilk for help, Tom quickly finds that he's on his own.

A visit from Loudermilk's alcoholic, philandering father opens old wounds and creates new problems.

Ben's secret life catches up to him, and Loudermilk is forced to confront the fact that he may not know his best friend as well as he thinks.

Loudermilk, Ben, and Claire hit the road for New Orleans with the intention of crashing a wedding. Left to their own devices, the group goes off the rails.

Loudermilk returns to Seattle and makes a huge decision that affects not only his life, but the lives of everyone in his world as well.