Angela Tries to Kidnap Jimmy's Son (Season One, Episode 11)
It's not like Jimmy has been the portrait of fidelity since first meeting Princeton waitress Angela Ianotti, but she's hardly been a saint, either. Throughout both seasons, Angela has grappled with her budding bisexuality, seeking comfort in the arms of girlfriends in her common-law (and eventually, legal) husband's absence. Toward the end of Season One, Angela, uncomfortable with societal restrictions and dreaming of a more bohemian lifestyle for herself and her son Tommy, attempts to escape to Paris with her lover, Mary Dittrich. The plan is thwarted when Mary absconds without her. A shamed Angela, with nowhere else to go, returns home to Jimmy. Their future remains ambiguous until Season Two, when it's revealed that Tommy's parents have reluctantly married.