When I first read your post, I thought she had a relationship with him.  Initially, I thought, "Oh no!"  Because we have heard similar stories before..., a good girl dates the bad boy, he abuses her, because she allows it....

Then I read the whole story, including all edits, then I realized, it's just a friendship.  So with that in mind, yes, I'd befriend with someone who genuinely repents.  Having a romantic relationship with him?  That probably is a long way to go.  (I've met a customer who told me he was homeless before.  He was quite handsome and was working as a janitor, but dating him... that could be a long way to go....  because the irrational fear he might carry some weird disease while living on the street scares me much like how this girl might never trust the guy who tried to rob him).

Truth is often stranger than fiction, and I know that is so because I've been through a few things that if I talked to people about them, they'd either be dismissive of such life experience, because they're so far-fetched, or think I deserve them, because I am being a stupid baby, completely green at the evils of the world.

But I could empathize with her.  Yeah, there had been one of those days when everything bad decided to unload onto you, all at the same time.  You just wanted to give up and be done with it (and that's very uncharacteristic of Ashi).  The fact she is a second-grade teacher made sense also.  If she wasn't so trusting, it's pretty hard to work in that environment.  I mean, she faces innocent kids everyday, and perhaps a little self-deceiving that's how the world should be, while knowing very well how the world is full of contradictions....  And must accept robbery being a normal part of the life.

Hope is a fairly dangerous thing.

But it is also a beautiful thing.

I'd give the guy who robbed her a chance, too, if he genuinely repents.  People like him isn't intrinsic evil, but a victim of the circumstance.  I've had various bosses who wouldn't hesitate to exploit others while claiming themselves to be self-made.  My family circumstance wasn't all that good.  Heck, I even ate reduced priced lunch back in high school, but my family never got to the point criminal act could be legitimized in order to survive another day.  So when I had my first retailing job, then I realized such pocket in the world exists....  Imagine how hard hit it was for me....

Then when I looked at those people in front of Home Depot, desperately tried to meet ends....  Come on, obviously the world has some issues we can't resolve, a little compassion to those who deserve it won't hurt anybody.  Call me too trusting if you like, but I won't feel bad for extending my hands a little.  This world needs a lot more love.