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.

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.

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.

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.

Abe is visited by his ex-wife and before he knows it, he's ready to say "I do" again.

After lending Dana money for a down payment on a co-op, Jack discovers her spending habits may not be in his best interest.

Ray is angry with Meg when she blabs about his personal life after being sworn to secrecy.

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.

Ray is left star-crossed after a date with Dana doesn't quite go as he had wished.

Murphy's Law is in full effect when Jack and Dana finally go out on their first "real date."