He smiles as she agrees to him and calling him cute.  He is glad that he could give her something that she desperately wanted which was simply time.  He was sad that his stupidity came with a price, but he was happy that in some fashion....he might be able to reverse that mistake, hopefully.  He looked at her while holding the door for her to the restaurant and smiled, "As always Madison, your beautiful."  He walked in after her and said, "Well choose where you want to sit."