Courting Disaster is the eighteenth episode of the sixth season and the 140th overall.


Searching for a movie-watching pal after Stuart opts out, Jack invites Grace for an afternoon at the theatre. However, when the duo discovers Stuart and a young

"Meet license and registration."

mystery man secretly catching a matinee, Jack is left questioning their relationship.

Elsewhere, Will attempts to teach Karen the skills of driving, but the road warriors have a run in with the law their first trip behind the wheel, prompting Will to fight the ticket in traffic court.





  • This is the first appearance of Vince, Will's new love interest. Vince is a friend of Joe and Larry. They have allegedly been trying to set up Will and Vince for years.
  • In the DVD commentary version of The Finale, the producers revealed that Vince was only supposed to appear in this episode, but they liked Bobby Cannavale's performance so much they decided to bring him back for future episodes.
  • The song Grace is singing (badly) is Hey Ya! by OutKast. Karen is later seen singing the same song in the outro.


Ladies and gentlemen, I find myself in a situation similar to the one Drew Barrymore is going through on the screen. Although, unlike her, I am not overacting. Jack

Vince:You know how fast you were going?
Karen:How could I? I'm inside it.
Karen getting pulled over for speeding

This isn't happy hour at the Cockpit. This is a court of law. Now get your ass out there and litigate, bitch! Karento Will

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