He is not out of your league, think of it this way, he met you 8 years ago, and saw what an amazing person you are, brilliant sense of humour, great fun to be with, and why, cos you are being you! the real you he has seen, so eh, come on girl no more hes out of your league, you have lost 4 stone, and that is one hell of a commitment, he can see you for who you are, and yes men do say the silliest of things, they have been prone to say, yes when you ask them does my bum look big in this, they are never going to get us properly, they do try, and its very obviously he likes you loads, why he over tries.
Give him the credit for that, but also give yourself credit, if he thought you was as horrible as you think, then he would not be with you, would he?