Most Helpful Girl
Well if you're a new guy and she doesn't trust you enough to tell you what's going on maybe the best option would be to "stay friends".
If you work on building a solid friendship,
I think it's more likely that she'll start telling you personal details then you can gage if it's something you can work with or around
Think of it this way: if you had some type of past problem. Who would you tell your new date or your friend?
If you told you date, I'd imagine it'd go something like this: Hey, I know we just met but I'd like to tell you that I just got out of an abusive relationship or I'm struggling with depression but don't worry I'm totally sane and dateable.
Not saying it's anything that serious but you get the idea...
Most Helpful Guy
What do you consider an undatable person's past? Like a pornstar of some sort? A prostitute? Used to be a man? What?