One could argue that Larry David, while not a looker, isn’t exactly a bad catch. He created one of the most successful shows (Seinfeld) of our time, is filthy rich, and funny, all of which helps balance out his rather meh looks and slovenly appearance.
What ends up tipping the scales way, way, way in Cheryl Hines’ favor is Larry's complete lack of social grace and etiquette. He thinks he knows the way the world should be, and though he's often right, he has no clue how to interact with people so he doesn't come across as an asshole. In fact, it’s so bad, one has to wonder how anyone is still his friend anymore, let alone eager to work with him. Cheryl, a much younger, attractive blonde, is a perfectly pleasant person could have done much better.