Season 3, Episode 23
May 18, 1999
After offering some unsolicited advice about Nina's tendency to make bad choices, Maya sees that it hasn't sunk in after catching her making out with a deliveryman. But when Maya interrupts their passionate kiss, she discovers that it's really an old boyfriend of Nina's who's just escaped from prison. In an effort to keep Nina out of trouble, Maya suggests calling the police. However, Nina is in no mood to send Roy packing and even agrees to hide him in her apartment. Meanwhile, Jack, Finch and Elliott all start betting on each other's habits and idiosyncrasies. When Nina decides to take Maya's advice and not plunge into a sexual relationship just yet, Roy is frustrated. After FBI Agent Justin Morris shows up unexpectedly, Roy hides. And in an effort to help him escape the apartment, Nina invites Justin to join her for a dinner out. However, after Nina falls for the FBI agent, too, she comes back home and is surprised to find Roy has decided to stay with her, no matter what. Meanwhile, their constant wagering begins to interfere with everything Jack, Finch and Elliott are supposed to do. In love with both Roy and Justin, Nina turns to Maya for help. For Maya, the choice is clear. However, when Roy sneaks back into the office for some advice about a gift, Maya cannot resist helping him out. Meanwhile, their non-stop betting has ended with Elliott, Finch and Jack too reluctant to do anything. Finally, after receiving a beautiful new coat, Nina decides to stick with Roy. But when she tells Justin of her decision, the sexually frustrated Roy is hauled off to jail.