tristan I would suggest that you table those talks that concern your feellings, it's easy to get into that trap but based on everything I've read, women just don't dig it.
You sound a little insecure when you give her those responses, as for her suggesting going to that place that she used to go with the OM too, I would just tell her "I think you can take me somewhere better than that dump, I know I'm worth it ;-)", you know tongue in cheek, smiling, having fun, etc.
It's easy to get drawn into those conversations and try to get her to feel what you feel but she can't, who can really feel what we ourselves feel, no one, just us. We would like them to feel our pain, our anxiety, our embarrassment so that they can take away some of that and smarten up so that they know not to go there and do that again but truth be told you can't.
As for the work thing, I would be conflicted as well. Why does she have to work with him? Can't she get someone else to handle the OM and his account with her company? Surely it doesn't have to be her. If you've read puppy's comments, you know what he says about renewed contact with the OM, it resets that clock and attraction again or at least it has the potential to and she needs to quit him cold turkey.
Take into account when she feels "it is hard and how much she screwed up" she associates bad & negative feelings with you and the relationship she has with you, sending an email to that dickwad OM regardless of what she says, those feelings & thoughts of fun times she had with him will creep into her head, how could it not, those memories can't be erased.
