Homer ruins Marge's chance to make friends, after getting into a fight with the Easter Bunny. Just when she thinks she will never have friends, a woman called Tammy (Lily Tomlin) offers her to join a group called "The Cheery Red Tomatoes". But as it turns out, her new friends are planning to rope her into a plan to break into the mansion of one, Montgomery Burns.
Meanwhile, Lisa ends of going to Milhouse for help learning to speak Italian, so she can go on a summer trip to Rome, while Milhouse tries to use the opportunity to romance her.
- Berserk Button: Do not speak English in front of Milhouses grandmother. (She was abandoned while pregnant by an American GI during the war).
- Bitch in Sheep's Clothing: Tammy and the other Cheery Red Tomatoes are a downplayed version of this, as they act nice to Marge and compliment her while recruiting her into their club, but once they reveal it was to rope her into their heist scheme and she proves to be reluctant to do so, they drop the flattery and threaten to kick her out if she doesn't go along. That said, Tammy is never outright hostile to her and they do have good intentions for robbing Mr. Burns.
- Call-Back: To "Summer of 4 ft. 2". Both episodes had a scene where the main focal character (Marge here, Lisa in the earlier episode) walks through town alone, lamenting the possibility that she's not meant to have friends.
- Coordinated Clothes: The group of friends called "The Cheery Red Tomatoes" wear red dresses and pink hats. Marge is very happy when they accept her as their member.Marge: I feel a happiness I've never felt. I not only have friends, I have a hat to prove it.
- Dye or Die: Played for Laughs. Tammy reveals that she isnt a natural redhead, which shocks Marge into fainting.
- Fictional Counterpart: The Cheery Red Tomatoes are based on the Red Hat Society (hence the episode title, even though the Tomatoes wear pink hats).
- Hairy Hammerspace: At the end of the episode, as Tammy laments the apparent failure of the Cheery Red Tomatoes' heist, Marge reveals she smuggled out at least one of Mr. Burns's twelve valuable Faberge eggs within her Beehive Hairdo.
- Kick the Dog: Instead of donating the check for $1 million like he had promised, Mr. Burns uses it to extend his own life by ten minutes and then releases the hounds (who were being brought to their groomers) at an angry crowd.
- Pet the Dog: After Mr. Burns catches Marge, Homer, and The Cherry Red Tomatoes at gunpoint, they manage to convince him to let them walk away after little water works, in exchange for giving him back his property.
Mr. Burns: *chuckles* Who's a stinky dog? You are! Michelle's going to work on you today! Yes, she is!
- A literal example occurs when Mr. Burns gives one of his hounds a good snuggle.
- Running Gag. Moe constantly landing on hot air balloons.
- Smart Ball: After being his usual idiotic self most of the episode, Homer manages to realize somethings wrong towards the end and goes to help his wife.
- Spotting the Thread: Homer realizes that Marge isnt birdwatching when she doesnt take any equipment with her.
- Your Cheating Heart: Milhouse almost succeeds in wooing Lisa into being his girlfriend while acting as her Italian teacher, until she catches him trying to romance another girl. Though it's possible this was a gambit to help her finish her Italian Lessons.