The context of the following conversation is In order to understand why Skylar was so bitter about life, Kendall decided to walk a mile in their shoes.:
Kendall says I just don't understand why Skylar is so bitter. I've decided to try to walk a mile in their shoes..
The friend responds I don't think that expression is meant to be taken literally..
Kendall responds Well, It can't hurt, can it? Hm. Actually these shoes are really tight. It really does hurt. No wonder Skylar is so bitter about life..
The friend responds Did you fall on your head as a child or were you just born that way?.