There's no Cinderellas here — Harry has almost exclusively gotten serious with women who came from extremely wealthy families. Chelsy was the daughter of Charles Davy, a successful businessman and one the the largest private landowners in Zimbabwe. Cressida is the daughter of Lady Mary-Gaye Curzon, a wealthy London socialite, and Jeffrey Bonas, a successful entrepreneur. It's unlikely that Harry has anything against dating nonrich women, but it's probably just that he runs in the same circles as rich people, so he's more likely to meet women from wealthy families. Besides, it would be hard to keep up with Harry's lifestyle without already having a considerable amount of money.