If Ponyboy and Johnny are Orpheus and Eurydice, does that make Bob and Cherry Hades and Persephone?
Bob as king of the underworld, the representation of wealth and greed, who orchestrates Pony and Johnny’s fate even from beyond the grave, who makes them play rigged games. Who loses himself when he loses the simplicity of being a boy in love with a girl.
Cherry as his queen who splits her time between the underworld and the surface, who has so much fun with regular folk who may be poor but who know how to celebrate the life that they have, to soak up the sun and savor their food and wine and dance and sing and feel, until her king comes to take her back down below. She pleads on behalf of Ponyboy of Johnny. She cannot avert the inevitable tragedy. She raises a cup to Ponyboy from afar, in sorrowful admiration for the way he makes music in the darkest nights. She is disappointed in her king. He’s not the boy she fell in love with. He still is. She still loves him.
My favorite doomed dysfunctional couple who really did love each other, who felt something real for each other in a social circle that’s too cool to feel anything.
Their meeting was the classic romcom trope of Bob falling head over heels for Cherry because she was the only girl who said no to him. She was the only girl who seemed immune to his charms that made all the other girls fall all over him, and his immediate reaction was “I must have her.” (No, this had nothing to do with his parental issues and subconscious need for someone to say no to him, shut up.) So he kept chasing her and she kept playing hard to get in a social ritual that was considered cute in the 1960s, until she finally agreed to a date.
At said date, Bob is suddenly nervous at the prospect of having to genuinely connect with the girl he likes. He rambles and trips over his words uncharacteristically and maybe spills a drink. He’s convinced he’s blown it but Cherry finds it adorable.
They really do fall in love with each other. They open up to each other on a level that neither of them had before, especially with people they dated. At first Bob tells himself he’s putting on an act to get into her pants cuz chicks dig the sensitive and vulnerable thing, until he’s finally forced to admit that he really is that gone on her.
They’re both attracted to what they see as the qualities in each other that are different from how the rest of the world sees them. In many ways they both feel like the other is the only one who knows the “real” them. Cherry sees Bob’s sweet, vulnerable, and even goofball side, and Bob sees Cherry’s passion and empathy and perceptive observations of their society and the people around them.
Bob is the biggest baby when he’s sick. Only with Cherry, though. He doesn’t want anyone else seeing him in any sort of weakened state. But with her, he’s whiny and clingy and moans that he’s dying even if it’s just a cold.
Bob really does want someone to say no to him, and he’s attracted to Cherry because she does. He is not however emotionally self aware enough to realize this. Consciously, he thinks he loves Cherry despite the times when she says no to him, when in fact it’s because of it.
Once Cherry told Bob that another (soc) boy was flirting with her, and Bob punched him. Cherry got way too much of a thrill out of that.
Cherry has “I can fix him” disease (which to be fair, girls were pressured to have in that era), and Bob feeds into it by telling her that she “makes him want to be a better man.” (He really does mean it, outdated attitude aside.)
The night that Bob and his friends jump Johnny, he shows up at Cherry’s house and drunkenly confesses what he’s done. She lets him have it, and he sorrowfully takes it until she softens and tells him she knows he’s better than this. He promises to try, for her. He really thinks he means it in the moment, as he always does. This has happened before. She tells herself that she’s helping him instead of enabling him.
