Just Shoot Me! (1997)

Season 3: Episode 23

After yet another relationship goes sour, Nina realizes that her lack of romantic success is probably due to her tendency to make bad choices in men. Her resolve to start making good choices is tested almost immediately when her old boyfriend Roy breaks out of prison and she falls in love with and begins dating not only Roy, but also the cop who is pursuing him. Meanwhile, Jack, Finch, and Elliott engage in a series of wagers on how predictable each other's behavior is.