Overview: Jack is devastated when he receives a Dear Jack letter from Wally, leaving the Blue Shamrock in Abe's care.
Overview: With Jack still heartbroken over Wally, the gang holds a get-together hoping to put Jack and Dana together. But it is far too soon for Jack.
Overview: Jack thinks a woman is flirting with him, so he makes a bet with Dana that he can get the woman's phone number before she leaves.
Overview: After Kip is nominated for a daytime television award, he invites the gang to the ceremonies and asks Dana to be his date. Monty Hall makes a guest appearance as himself.
Overview: An old-fashioned barroom brawl breaks out at the Blue Shamrock: Jack takes a few punches after a couple of macho patrons hit on Dana.
Overview: Dana's dinner invitation to Jack is not just a kind gesture as she has a secret agenda—she needs help moving furniture.
Overview: Dana's best friend comes to town and warms up to Jack. When she feels a "spark" for another guy, she drop Jack cold and asks Dana handle the mess.
Overview: Much to his displeasure, Jack is temporarily assigned to his newspaper's style beat and covers the closing of a department store.
Overview: When Jack sees a doctor about a private problem, his agitation at having a female physician is worsened when he bumps into Dana in the reception area.
Overview: While attending the Macy’s Thanksgiving Day parade, the gang ends up doing some unexpected babysitting when a woman leaves her boy with Jack.
Overview: Jack and Dana go out as friends, and everywhere they go, they are mistaken for a romantic couple making it harder for them to keep things platonic.
Overview: Jack and Dana discover that their feelings for each other have reached a new level when they get stuck in an elevator at the Empire State Building.
Overview: Dana takes Jack shopping to convince him that salespeople discriminate against women.
Overview: Meg introduces her new beau to the Blue Shamrock group, who are all astonished by his resemblance to Jack.
Overview: Everyone thinks a college student has a crush on Jack -- except Jack.
Overview: Abe is visited by his ex-wife and before he knows it, he's ready to say "I do" again.
Overview: After lending Dana money for a down payment on a co-op, Jack discovers her spending habits may not be in his best interest.
Overview: Ray is angry with Meg when she blabs about his personal life after being sworn to secrecy.
Overview: Jack acts like a protective parent when his visiting mom has a night on the town with Dana's flamboyant father.
Overview: Nadine entertains the prospect of a relationship with a handsome literature professor.
Overview: Ray is left star-crossed after a date with Dana doesn't quite go as he had wished.
Overview: Murphy's Law is in full effect when Jack and Dana finally go out on their first "real date."