Well the fundamental problem is that Fran doesn't seem to like her, flat out. Nobody can figure out why he keeps dating her, or wants a long term relationship with her. If his professional reputation is at stake AND he seems to view her as inappropriate most of the time, then why is he dating her?

Sure, but we assume that our friends also love us the rest of the time when we're not being dicks. Fran doesn't seem to like Hannah much at all even when she's not being a dick; he thinks she's being a dick all the time, essentially. He's not saying "Hey I love you but you're acting out of character by being a dick…

It's not his place to change her. No one else has any right to change another person, even for their own good; the change has to come from the person themselves (so long as no one is getting hurt.) Plenty of controlling people think their partner should be changed/controlled because otherwise their partner would make…

Eh I don't think Fran could offer her a stable or mature relationship, either. A stable/mature relationship is based on the idea of accepting your partner and encouraging them to be the best version of themselves. Hannah, even a mature, stable Hannah, is always going to be Hannah; some version of kinda inappropriate,…

I tend to lean towards thinking he's a jerk, cause the thing is, Hannah has been fairly upfront about who she is from the beginning. I mean, their first date seemed to display her tendencies pretty clearly. It isn't as if she hid the crazy and then poured it on him when he was in good and deep. Yet he dated and then…

I know Hannah has never been the most mature or balanced individual, but flashing her boss seemed so beyond the pale even for her I'm trying to figure out the motivation.