- "I understand boys. Boys show what they feel. Boys' friends are their friends. Girls are the ones to watch out for."
As summer vacation draws to a close, Karen's moles in Penny's and Aggie's cliques make their first moves. Cyndi, apparently suspecting Sara's gay, casually flirts with her in front of her friends, and drops the first of many hints to Michelle (previously established as having body issues) that she should watch her weight. Meanwhile, Helen reminds Aggie of her ongoing feud with Penny (whom she hasn't seen for months) by suggesting Aggie can accomplish a lot in the coming year if she doesn't let Penny get in her way.
On the first day of school, Penny, Aggie and Stan are excited to learn that the school has hired Hollywood director Calvin Machrie for Macbeth, the first of three school plays for the year. Faced with a disproportionate number of girls auditioning, Machrie decides to disregard gender in his casting, and chooses Penny for the title role, Aggie as her nemesis Macduff, and Stan as the future king Malcolm. The question of whom to cast as Lady Macbeth gives him pause, until he observes Sara brokering a truce between her two closest friends, for the good of the play.
Karen continues working behind the scenes against her arch-rival by talking Stan into finally breaking up with Michelle, who has naïvely continued to believe that he loves her. So when he tells her he doesn't want to be tied down, she's shocked and devastated. Making matters worse, Stan, at Karen's urging, adds coldly that her continued friendship with Penny has bothered him.
Jack and Katy-Ann, encountering each other for the first time since she left for Sri Lanka, discover that they'll be working together on the play as stage managers. This proves awkward at first, in that Jack hadn't written Katy-Ann all summer. When pressed as to why, he tells her he'll inevitably let her down, so better that she realize it as soon as possible. Hurt, but collected as usual, Katy-Ann comments on his self-esteem problem (a recurring issue with Jack). She points out that it's his loyalty to Stan, his never having let him down, that attracted Jack to her and adds that, since she's looking for a long-term relationship, she'd thought he might be the one, but was apparently wrong. She walks away.
At the same time, Samantha picks a fight with Penny in front of her clique, accusing her of casually dropping her friends (Helen, Katy-Ann) and asking whether the next one will be Brandi, her "token nig—". As Sara angrily cuts Samantha off, Penny calmly puts her in her place. However, unbeknownst to Penny, Samantha isn't working alone. Immediately afterward, Cyndi plants in Brandi's head the notion that Penny may be angry with her for not standing up to Samantha as Sara had. As a result Brandi, already hinted at earlier in the chapter to still be unhappy with Katy-Ann's ouster from the group, blows off Penny's monthly party to play basketball with her brother and his friends (see page quote).
The next day, Jack lets a delighted Katy-Ann know he's interested in a relationship after all. An innocent but humourously misunderstood remark on her part leads her to clarify that she wants to take their relationship slow, and Jack to agree that he's willing to wait, saying he's "playing the long game" too. He adds, wryly, that nonetheless he enjoys seeing her get "a little bit reckless" around him. (This, too, will be a recurring theme in their storyline.)
As the rehearsals proceed and Machrie drives the students to exhaustion with his requests for do-overs and bizarre yet constantly-changing acting instructions, Penny, Aggie and Stan find themselves chatting sympathetically with each other for the first time. And even when they all pause and silently realize what's going on, they're all too exhausted (or tell themselves they are) to resume their verbal sniping just yet.
At her last-Saturday-of-the-month party, Penny frets to Sara about the unexpectedly sparse attendance, noting that even Michelle and Brandi haven't shown. Meanwhile, Stan brings Jack to the first of Karen's parties, featuring alcohol-laced popsicles.
- Beautiful Dreamer: A non-romantic, parent-child version with Nick smiling as he watches Aggie sleep with a Cat Smile on her face. Subverted in that Aggie, having been told Macbeth's death will occur onstage in this production, is having a not-so-innocent dream of killing Penny in several cartoonish ways.
- Comeback Tomorrow: When Aggie overhears Penny saying that playing Macbeth will allow her to express her "inner bitch," she counts to a hundred before yelling out the retort, "Inner??", well after Penny has gone. Presumably this is in order to avoid a fight.
- Driven by Envy/The Resenter: Helen, with regard to her former friends, the Pennies. Here, unlike in other arcs where this trope of hers appears, she expresses it openly, to Sara, rather than via inner monologue.
- Erotic Eating: At Karen's party, Cyndi and Meg give the boys a new twist on Faux Yay teasing, by seductively sucking each other's popsicles.
- Even Evil Has Standards: Stan rejects Karen's suggestion that he get Michelle to break up with him by ordering diet salads for her at restaurants, "and put[ting] a little emphasis on the word 'diet.'" He says he can't talk that way to a "lady."
- Faux Yay: Cyndi flirts with Sara in front of her friends, possibly in an attempt to out her. (At this point, Penny knows Sara's gay but Michelle and Brandi don't).
- Have I Mentioned I Am Heterosexual Today?: Sara, ignoring Brandi's warning not to discuss it in front of Michelle, talks enthusiastically and somewhat crudely ("Slrrrp") about Stan having given Brandi oral sex at Karen's birthday party. Recall that she hasn't come out to any of her friends except Penny, although the same strip shows that Cyndi's figured it out (see above under Faux Yay).
- Insecure Love Interest: Jack.
- Large Ham: Fred, playing the First Witch.
- Lets Wait Awhile: Katy-Ann and Jack both agree to this.
- Manipulative Bastard: Karen and Cyndi, the latter of whom begins to show her true colours in this chapter. Her line "I will destroy you!", said as a joke to Michelle, nearly comes true literally, later in the arc.
- N-Word Privileges: Samantha invokes this, but Sara cuts her off before she can say the entire word.
- No Celebrities Were Harmed: Calvin Machrie physically resembles comedian Colin Mochrie, while his personality and directing style are modelled after Mochrie's recurring character on Whose Line Is It Anyway?: the "Hollywood Director," whose schtick was constantly having his actors redo a scene in outrageous ways.
- Please Dump Me: Discussed by Stan and Karen, with regard to Michelle. Stan, however, finding Karen's suggestion for invoking this trope too cruel, opts to dump Michelle directly.
- Reading the Stage Directions Out Loud: Penny: "Exzoont [sic] fighting." note
- Sadist Teacher: Lampshaded by Principal Giuliani.Welcome back. This institution is important to me [...] because it provides a healthy outlet for my sadistic tendencies. (Student laughter) Everyone thinks I'm joking about those. (More laughter)
- School Play: Macbeth, which serves both in "The Popsicle War" and in the later arc "Final Curtain, First Kiss" as a commentary upon several of the comic's characters and their stories.
- Shout-Out: Among the ways in which Aggie kills Penny in her dream is shooting her while dressed as Elmer Fudd.
- Silent Bob: By approaching Katy-Ann with the single word "Okay," Jack lets Katy-Ann know he's made up his mind about dating her seriously.
- Terrible Interviewees Montage: Machrie suffers through a number of students' inept or inappropriate readings of Lady Macbeth's "Screw your courage to the sticking place" speech, before finally casting Sara.
- Unrequited Love: Michelle, for Stan.
- Wingding Eyes: Penny's, Aggie's and Stan's reactions to the announcement that Machrie will be directing the school play.