"You know, I think I like you because you're so honest"
"Shut up, all I do is lie. The first thing I told you was a lie."
"Even when you lie, you're still being honest. It's your face."
"Don't mistake an honest face for an honest person; that's how I got my second broken heart" She smiles proudly, because she knows he considers broken hearts a badge of honor, something that makes you a more interesting human being. Too many broken hearts though, and you are overly-sensitive and naive. Too few, and you are still just a kid with nothing interesting to say. She has decided her heart has been broken twice. But she only knows for sure who one of them was. The first time her heart was broken (and she will NEVER tell him this, because she knows it will strip all the somber dignity out of the situation) she had only been dating the guy for two weeks. By most standards, that doesn't even qualify for a relationship, let alone a broken heart. So she combines the first story with ones that came after, finds it easy to make all boys into one boy, to not change the situation or the course of events but just SAY that her heart was broken here, here, and here, when really she remembers not wanting anything more in that situation than to get away.
The second broken heart was more traditional and can be labeled, but she still is lying.
He looks at her skeptically, but she knows the suspicions are for all the wrong reasons. He really does believe that she has an honest face and therefore is honest, while she knows that her second broken heart came not from his dishonesty, but from her own.
So it goes- either way they are both wrong, and she is back to square one, although, she thinks, the fact that he said anything at all is a step in the right direction.