Main character is a jerk. Despite being rich, he can't seem to keep females around. He is unwilling to put up with a trophy wife (i.e. a gold digger). Through the input of his past dates, he realizes that he cannot keep women if he is a jerk.
So, for his next date he pretends to be a nice guy. He screws up enough that she is well aware that he is a jerk but she is poor and desperate after leaving a recent abusive relationship. So, she acts as nice as she can and does whatever she can to make sure he will keep dating her. Over time, he discovers that not being a jerk is easier. He picks up on the way she sometimes cringes when he makes a cutting remark and realizes that he really doesn't like it when it happens. Her attempts at being friendly seem a bit too forced after he is cruel and he much prefers her normal behavior. Over time, the pair fall in love.
This would work OK as a harem story too, with his actions initially being that of a man who just wants to have multiple women and later being that he falls in love with them all.
So, for his next date he pretends to be a nice guy. He screws up enough that she is well aware that he is a jerk but she is poor and desperate after leaving a recent abusive relationship. So, she acts as nice as she can and does whatever she can to make sure he will keep dating her. Over time, he discovers that not being a jerk is easier. He picks up on the way she sometimes cringes when he makes a cutting remark and realizes that he really doesn't like it when it happens. Her attempts at being friendly seem a bit too forced after he is cruel and he much prefers her normal behavior. Over time, the pair fall in love.
This would work OK as a harem story too, with his actions initially being that of a man who just wants to have multiple women and later being that he falls in love with them all.
