I LOVE ALL OF THIS SO MUCH. first loves 1000000%. he prob would have been all messed up about her disappearing which could totally be a reason as to why he's such a playboy now. idk if he would pay for her for the night, but I can totally see them spending time together snd he'd give her money. I know it sounds like the same thing, but in his head he's helping out "the one who got away" and it's always way more than what she would normally get paid bc he wants to make sure he's ok. SO HE KINDAAAA has a soft side, but like no one really knows about it but her. when she does take stuff he probably will send her clips from his security cameras of her taking whatever souvenir she chooses that time
I kind of see them being super cute and innocent before her life gets turned upside down and before his father gets his hooks in him and turns him into the heartless money grubber that he is now. on top of the fact that she disappeared. AND NOW they're both these guarded crazy people