Most Helpful Guy
It's probably his attempt at showing playful affection.
What a lot of women don't realize about men is that that is how we tend to show affection to each other.
What a lot of men don't realize is that this sort of thing often makes women insecure and/or doubt themselves.
Women: "how do I look?" --- "you look fantastic!"
Men: "how do I look?" --- "like someone beat you with an ugly stick"3