Can we not do the whole "women are objects to be ranked based on physical appearance only and fought over as prizes" thing, please? That prom queen has agency of her own-- who's to say she's even into the "winner", let alone that their personalities are in any way compatible? Maybe (assuming she's interested in men and looking for a relationship) she'd rather be with a guy who isn't hypercompetitive, who's more laid back and easygoing?
Which brings me to the other problem with your metaphor: what's "winning"? Someone could be doing well by society's metrics and be miserable, because their current lifestyle isn't the right fit for them. Someone else could be a total failure by society's metrics, but perfectly content with their life the way it is. Who's the real winner there? (Spoiler alert: it's the second person).