She's been watching over him ever since they were little. She knows a lot about him. She understands what he's been through that caused him to be what he currently is.   He's totally clueless about her presence. He didn't know he's being watched. He doesn't care about anything anymore. He's totally broken.  

He's a sought after bachelor. One who can have whatever he wants... including WOMEN. When his only sibling died, he was left with twins to take care of... and he felt burdened because of that.