"I know what you say about me. You say I'm 'low-rent.' Say I'm trapped. Say I'm never gonna have nice, expensive things. Wrong. I'm gonna have you."
Aspiring skater boy Rich Diggle sets his sights on winning Penny's affections. He starts by directing snark at her, in front of Sara and Michelle, for being stuck-up. His "bad boy" attitude attracts Michelle's interest, which he exploits by inviting her for rides on his scooter. Penny at first ignores his pot-shots and the "thing" he now seems to have with Michelle. However, when Rich calls her "gutless" and Michelle lets slip that she agrees, Penny begins riding with him too, initially to save face, but soon developing a snarky flirtation with him, culminating in her inviting him to an exclusive club party. As they slow dance for the first time, and Penny finally shows genuine affection for Rich, Sara consoles a heartbroken Michelle.
Penny quickly makes Rich the centre of her life, dressing in "skater grrl" outfits and adopting his slang. At the same time, she's not above seizing the opportunity to further her acting and modelling ambitions by hosting his online skating videos. While Penny and Rich are happy, their friends are not. Michelle is still quietly resentful at having been used, while Sara worries that Rich is changing her best friend beyond recognition, and tries finding a sympathetic ear in Aggie. Although Aggie professes not to care, she is in fact intrigued by the possibility of Penny becoming "less patriarchal" by dating outside her "class." Witnessing Rich beat up a boy (later given the name Gary) in the alley, with the help of his friends Stan Larson and Jack Kirk, for having called Rich "whipped," disgusts Aggie, but she still declines to get involved for now. For their part, Stan and Jack, annoyed at Penny having insinuated herself into their idol's every skating video session, quietly wonder whether Gary may be right.
Eventually, cracks begin to appear within the relationship itself. While Penny can deal—barely—with a Rich fangirl getting her name wrong, she's so bothered by his not wearing a helmet while skating, because he feels it'd compromise his image, that they have their first of several fights. Rich gives in on the helmet issue, annoying Stan and Jack all the more and prompting them to lecture him for losing his "edge." As both lovers become increasingly alienated from their friends, Aggie, overhearing a conversation between Sara and Michelle about Penny and Rich fighting and her "puffy eyes," thinks that Rich is beating her and resolves to offer her help. However, by the time Aggie catches up with her, Penny's already dumped Rich via text message after he stops wearing the helmet. Both Penny and Rich think to themselves that the other will "come crawling back," indicating not only that they still have feelings for each other, but that the real
problem with their relationship was their clashing egos and individual need to be in control.
- All Girls Want Bad Boys / All Guys Want Cheerleaders: Penny isn't a cheerleader as such but, as an affluent, popular, somewhat elitist girl, otherwise fits the fantasy type where Rich is concerned.
- Badass Biker: Rich.
- Conflicting Loyalty: Penny and Rich experience this with regard to their friends and each other. Also Michelle when she initially becomes interested in Rich but fears Penny's scornful reaction ("He, he, he looks dangerous. Boring! I mean boring!").
- Dance of Romance: Penny's and Rich's first dance is when it first becomes clear—to the two of them, as well as to Sara and Michelle looking on—that their pursuit of each other is more than just a game of one-upmanship.
- Defrosting Ice Queen: Penny is initially cool, dismissive and mildly contemptuous toward Rich, but gradually falls for him and shows it.
- Disappeared Dad: When Rich tells Penny his father isn't worth talking about, she thinks he means he deserted his family, when all Rich means is that he sees him as an uninteresting factory worker.
- Don't You Dare Pity Me!: Played with in a one-off gag strip at the end of the arc. Aggie, suffering under the hot sun during a protest, hesitates to accept the bottle of water that Penny offers her in passing: "I'm not sure I'm that thirsty." It doesn't help that Penny can't resist gloating as she does so.
- Dresses the Same: Aggie invokes this against Penny in another gag strip at arc's end. She goes shopping during lunch for an uncharacteristically girly outfit, simply because it's the same one Penny's wearing that day.
- First Love: Rich is this for Penny. Previously, she considered boys to be "like Skittles," and unworthy of attachment.
- Helmets Are Hardly Heroic / Safety Gear Is Cowardly: Rich claims that wearing a helmet when skateboarding would be, in effect, saying he expects to wipe out, or like shouting "I might lose!" at the beginning of a boxing match.
- Henpecked Husband: Although Rich and Penny aren't married, this trope best describes how Gary, followed by Stan and Jack, and ultimately Rich himself, view his role in the relationship.
- I Want My Beloved to Be Happy: Michelle, with regard to Rich, in this strip.
- Make Up or Break Up: This arc is just the beginning of Penny's and Rich's stormy relationship.
- Sarcastic Devotee: Jack toward Rich.
- Those Two Guys: Rich's wingmen Stan and Jack. They emerge more as personalities in their own right in subsequent arcs, but the seeds of their contrasting characterizations are here.
- Unrequited Love: Michelle for Rich.
- Uptown Girl: Subverted, despite the arc title. Penny initially dislikes Rich and it takes time for him to win her over. Also, the relationship ultimately doesn't work out.
- Yes-Man: Stan toward Rich, until he voices his concern that Penny has domesticated him.