bob sheldon is the king of a grand romantic gesture. He doesnt just get cherry flowers or an expensive piece of jewelry, he takes time in learning what cherry genuinely likes and wants, he notices when she needs things, and he’s all about orchestrating some fun or chill date for them, depending on what he thinks she needs. And he makes sure that he doesn't just do these gestures as apologies when they fight after he gets drunk, he’ll sprinkle them in on random days. Call it manipulation maybe, that he makes sure cherry doesnt feel that he only does big romantic things so she’ll forgive him. Or maybe call it sweet. It depends on how you look at it. Cherry thinks it’s sweet.
the thing is, he’s the complete opposite of trip. Cuz when trip and marcia fight, as they very often do, he rotates between flowers, chocolates, or/and expensive jewelry based on the severity of the argument. And marcia is sick of it.