Liz searches for a man she met in her dentist's waiting room. Jack fears for the future when he learns a cable company may have its sights on NBC. Jenna helps Tracy try to get a Tony award.

Jack needs to reestablish himself within the new corporate structure. Liz and Wesley continually run into each other, making them consider fate's role in their lives. Tracy's nanny writes an exposé.

Jack becomes even more entangled in his love triangle between Avery Jessup and Nancy Donovan, and he turns for advice to Liz, who is focusing on her own romantic problems. When Liz can't find a date to Floyd's wedding, she revisits her old boyfriends in hope that a spark will reignite. Meanwhile, Tracy continues his journey to earn his egot.

Liz questions fate when she meets the man of her dreams, while Jack's love triangle between high school love, Nancy Donovan, and CNBC anchor, Avery Jessup, comes to a head. Meanwhile, Jenna's boyfriend is confronted with a similar dilemma when his desire for another woman threatens to ruin their relationship, and Kenneth, with the help of Tracy, tries to avoid a promotion that would land him in LA.