Nathaniel Plimpton III

Nathaniel Plimpton III arrives at the law firm as the boss's son and Rebecca's new coworker: polished, entitled, and needling, with a smirk that suggests he's never once doubted his own charm. He's competitive by instinct, dismissive of feelings as a category, and clearly used to getting what he wants without trying too hard.

The show hands Scott Michael Foster a stock rich-jerk archetype and then keeps undercutting it with musical numbers that expose exactly how much performance the confidence requires. Foster plays the cracks with comic precision — a golden-boy exterior stretched over someone visibly startled by his own feelings — which makes the character's slow thaw funny before it's ever sincere.