Pop's old chum, Tim, passes away, Pop throws a wake for him, and the occasion brings Kit back to Boston.
A woman wants to make a film about Pop.
Pop's attempts at fixing Kit up with a Little League baseball coach don't go over quite as planned.
It's not a very merry Christmas when Pop picks the holiday season to attempt to stop a shopping center from being built.
Father Chuck, Jr.'s plans to climb the ladder aren't helped by his father's bitter feud with a clergyman in their church, nor by his own untruthfulness.
Kit gets sick of living with her family again, and decides to return to show biz.
Pop and Chuck find themselves on opposite sides of a strike at the Cavanaugh Bros. Construction Company.
Neither Pop nor Chuck like that Kit has taken it upon herself to allow Mary Margaret to start dating.
Pop is humiliated when he loses his driver's license due to his failing eyesight. As if that's not bad enough, Kit is trying to sell his car out from under him. Pop discovers Kit's plans when Maureen Brennan, an elderly, outspoken widow just like him, drops by the house asking to see it. Although Pop refuses to give up his '41 Plymouth -- which he courted his wife in -- without a fight, he falls for Mrs. Brennan and agrees to take her for a spin, license troubles and all. Officer Dennis ends up escorting him home, because, as Pop claims, he crashed the car into a tree. But when Mrs. Brennan comes by the house a second time, Chuck and Kit learn that she asked Pop if she could drive, and the accident was all her fault. As it turns out, she still wants to buy the car, as her dead, Irish husband Robert courted her in a '41 Plymouth. A smitten Pop finally agrees to sell it, and Mrs. Brennan repays him with a little backseat nookie.
Two of Kit's fast and loose showgirl friends from the '70s, ""Legs"" Lawler and Crystal Line, plan a trip to Southie to stay with Kit for a night, before the three of them head out to Atlantic City together the next day for a ten-year reunion of former showgirls. But even that short amount of time is too long for Pop, who doesn't want Kit's trashy friends in his house, because he assumes they'll be a bad influence on Mary Margaret. Although Kit gets her way, that night after she goes to bed early, ""Legs"" and Crystal drink champagne with the awestruck Mary Margaret present, leave the bottle there, and Mary Margaret helps herself and gets smashed. Pop catches the aftermath of this, alerts Chuck, and they both demand that Kit throw the diabolical duo out. With Mary Margaret suffering a bad hangover, Kit does just that, and tells the girls she's not going to the reunion -- not because Pop said she couldn't, but because she realizes she's changed since coming home.
When the church sets up Father Chuck, Jr. rating videos for family consumption, he discovers something about Kit he didn't know.
All hell breaks loose when Pop's wealthy, estranged brother, owner of Cavanaugh Bros. Construction and Chuck's boss, James ""The Weasel,"" pays a visit to the Cavanaugh house, against Pop's wishes. James wants Pop to know that an old basement office they once shared is going to be demolished. Inside the office is a locked safe, each of them has only half of the combination, and Pop stubbornly refuses to hand over his half. The two brothers are forced to work out their 30-year-old differences when they both arrive at their former office. But their bickering causes the staircase out of the building to collapse, leaving them trapped inside just hours before the demolition. While looking for a way out, Pop finally agrees to share and share alike, and his seeing the prized family memories that James saved in the safe leads the pair to have a reconciliation right before Chuck and Kit rescue them.
Kit has trouble dealing with Kevin's attempts to pass her off as his mother for an upcoming parish talent show.
James returns, and he and Pop dig up the past concerning their childhood rivalry over the affections of a girl.
When Kit's ex comes to town, Kit realizes she still has feelings for him.
Chuck can't swallow his pride when Kit outdoes his efforts at the construction company.
The Cavanaughs think a week in a monastery is just the thing that will teach them to get along.
Pop's plan to help Kit fight a tax audit gets him in hot water with the I.R.S.
When Kit struggles to quit smoking, the rest of the clan agree to give up something of their own to support her.
A politician rejects Pop's offer to handle his campaign, because he's too busy setting his sights on Kit.
Father Chuck, Jr. is in a bit of a bind when the homeless shelter where he was helping out is forced to closed down suddenly. He's managed to find a new home for everyone, save for one person, and asks Pop if they could stay with him temporarily. Pop reluctantly says yes, only to learn that there's two people: a Hispanic woman, Rosa, and her infant son, Bob. But when Rosa (who barely speaks any English) overstays her welcome, Pop and Kit begin to suspect that the Father's motives aren't entirely pure, and Rosa is a scam artist. They get one right -- Father Chuck, Jr. goes on to announce that he's resigning from the priesthood, so that he can marry Rosa and be the other kind of father. Although everyone takes the news hard, only Pop is so angry about it that he nearly disowns his grandson. Pop's increasing feelings towards the baby cause him to eventually have a change of heart... at the same time that Junior has his own about the marriage thing.
The family think Mary Margaret has been bitten by the acting bug, but she's actually been bitten by the love bug after gaining a crush on a boy who's choreographing her school play.
Deciding Chuck has had enough time to grieve over Nora's death, Pop gallantly sets him up on a blind date. Since Chuck doesn't have the backbone to do so, Kit tells Pop that he has no right to play matchmaker for his son, especially since Chuck is too shy to be fixed up. Despite Kit's protests and Chuck's desire to remain a one-woman guy, Chuck ends up going through with the affair... albeit with a toupee. Although his date, Bonnie, is better-looking than he is, and a good ten years younger, the two of them have a couple things in common -- her mother fixed her up, and she's no more confident on the dating scene than he is. But he comes home from their dinner date feeling like he did everything wrong, starting with his failing to admit to her that he's balding. When Pop apologizes to Chuck for meddling, claiming that he didn't want to see him end up alone like he is, Chuck nervously sees Bonnie a second time, sans the hairpiece -- after which he learns that she knew all along, and like
It's Pop's 72nd birthday.
James tells the family that he is getting married. But is he?