As Sophie Berger plays mahjong with her friends and learns intimate details about their love lives, grandson Nathaniel rushes in quite verklempt. Evidently older brother Alan let it slip that someday Natie will die. Reassured that he will live forever, the 9-year-old lad is escorted back to his apartment just upstairs.
Phyllis, a working mom, discusses Alan's homework as she gets ready to leave for work. Breakfast will be at Grandma's as usual. But before heading downstairs to Sophie's, Alan makes his case yet again to his mother for the family to get their own phone. It seems he has a new friend and she is of the female persuasion and getting or sending calls from Grandma's is a bit awkward for the budding adolescent.
The point is driven home when Alan indeed receives a call from Katie, his new female Catholic friend, much to the chagrin of Grandma Sophie. Walking to school with his friends Benny and Warren, Alan discusses what else? Girls! And then there she stands, red curls and a smile that would melt the polar ice caps – Katie Monahan and her friends. Small talk, nervousness and Benny's social gaffes ensue.
Another "Benny" moment in the school bathroom with the tough hoods prompts Warren to tell Alan that the guys want Benny out of their club, named The Royals.
In social studies class, Mr. Greer encourages the class to start reading The New York Times, a serious source of news as opposed to The Daily News, a tabloid. Another example of Benny's unique style is highlighted.
As the time for the big school dance draws closer, Warren threatens to kick Benny out but Alan, in an earnest attempt to spare Benny's feelings, says he will do it. A failed attempt to spin the move as a positive leaves Benny running away, hurt and rejected.
Meanwhile, Sophie takes Nathaniel and Nicholas to the bank where the great Gil Hodges is making a personal appearance. Grandpa Jules shows up and Hodges plays along with a concocted story Jules told Natie about the two of them playing baseball together in Russia.
Phyllis notices Alan's dejected demeanor and helps him get ready for the school dance, including dance lessons, Arthur Murray style. As "Earth Angel" plays in the background, the scene switches to the dance as Alan and Katie stumble around. They briefly explore some differences between the Catholic and Jewish faith. When Mr. Greer inquires about Benny, Alan clumsily tries to explain his friend's absence as he spots his friend on the outside looking in.
After the dance, Alan seems distracted at the malt shop and Katie mentions it. But the date ends well because Katie mentions that there would be a "next time."
As Alan arrives home, he finds Sophie babysitting. A heart-to-heart scolding finds Alan sufficiently rebuked for the way he has treated his life-long best friend. Alan goes and apologizes to Benny for going along with The Royals instead of his friend. Benny forgives Alan and the friendship is saved. Alan tells Benny that Katie thinks Benny is cute.
George Silver, Alan's dad, comes home from working the late shift and gets an abridged version of the days events from his two sons. As the three head off to bed, Sophie watches out her window till the light goes out, assured that her family is once again safe and sound on a Brooklyn night.