Jack is devastated when he receives a Dear Jack letter from Wally, leaving the Blue Shamrock in Abe's care.
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.
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.
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.
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.
Dana's dinner invitation to Jack is not just a kind gesture as she has a secret agenda-she needs help moving furniture.
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.
Much to his displeasure, Jack is temporarily assigned to his newspaper's style beat and covers the closing of a department store.
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.
While attending the Macy's Thanksgiving Day parade, the gang ends up doing some unexpected babysitting when a woman leaves her boy with Jack.
Meg introduces her new beau to the Blue Shamrock group, who are all astonished by his resemblance to Jack.
Everyone thinks a college student has a crush on Jack—except Jack.
After lending Dana money for a down payment on a co-op, Jack discovers her spending habits may not be in his best interest.
Jack acts like a protective parent when his visiting mom has a night on the town with Dana's flamboyant father.
Nadine entertains the prospect of a relationship with a handsome literature professor.
Jack and Dana's night together gives way to disappointment.
Jack gets into trouble for using the handicapped stall at a diner.
When Nadine hosts a birthday party for her husband in prison, Jack and Dana do some cell mating in the conjugal visiting room.
Jack and Dana's methods of relaxation clash during a Mediterranean vacation.
Jack watches as a long-lost love waltzes back into Dana's life during a dance marathon.
A wary Jack submit to a mammogram after Dana discovers a strange lump in his chest.
Jack moves in with Dana and reluctantly sublets his apartment to Ray.
Meg's relationship with a New York Knick becomes public domain after his performance on the court seemingly become linked to their performance in another arena.
Abe is outraged when a homeless man sues the Blue Shamrock, claiming that a free meal gave him food poisoning.
Ray must face his own bigotry when his blind date turns out to be black.
Regulars at the Blue Shamrock share their memories of a landmark movie theatre that's about to be torn down. (Part 1 of 2)
Conclusion of two-parter. The bar patrons share more memories of a landmark theater that's closing and Jack tells of spending an evening there with his father.
The gang takes Nadine out on the town after her divorce is finalized.
Jack and the gang suspect that a flamboyant man and his entourage who have made the Blue Shamrock their new hangout may be gangsters.
INS agents arrest an unlikely suspect when they visit the Blue Shamrock to look for illegal aliens among the employees: it seems Dana isn't a US citizen.