Most women tend to show only their serious side, all manners, rules etc. This is where they go wrong when dealing with men. Every once in a while, it is important that you show him your crazy side too. Break into random dance moves, sing something, order a pizza and break the imposed weight loss rule, ask him out on a random date for bowling or snooker, something he loves. This makes him feel more comfortable and that he can have fun with you and open up.