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Look, we're not fond of this label either (unless it's being applied to Rachel Bloom's brilliant show) but Eggers isn't giving us much choice here. Ruby is cast as the typical crazy ex-wife/hot mess/basket case.
After all, she:
Whoa there, Ruby.
But interestingly, even though Ruby's madder than the Mad Hatter, Alan doesn't feel that he's in a place to disrespect his former wife. Even though he recalls all the bad stuff about her, he's reluctant to say a bad word about her. In fact, Alan's pretty willing to take some of the blame for how things turned out between them.
He's absolutely certain that she would have been a different person if they hadn't hooked up:
She was charming as hell, radiant. She saw everything, met everyone. She was a dazzling guest, the most headstrong and intellectually curious and vivacious American any of them had ever known.
But she was embarrassed about Alan. (XX.50.175)
Ruby has a lot going for her: intellect, beauty, and passion. But she also has a cruel streak a mile wide. She's dissatisfied with Alan because he's not powerful enough socially to help her achieve her social agenda (also, he's not as smart as she would like). Her sense of freedom and progressivism are also too much for Alan to bear.
She wants to share everything, thinking it will make them (her?) stronger:
They had fought repeatedly, explosively, mostly about their exes. Ruby wanted to talk about hers, in great detail. She wanted Alan to know why she'd left them and chosen him, and Alan wanted none of it. Was a clean slate too much to ask for? (IV.15.31)
And it goes without saying that she brings out the absolute worst in Alan. To us, Alan seems pretty chill. Yeah, he's socially awkward, nearly always does the wrong thing or makes the wrong choices. But he's willing to turn a blind eye to Brad and Rachel making out in the tent, and seems okay with doing whatever Hanne wants.
But in the face of Ruby's provocations, Alan becomes a totally different creature:
His only weapons against her were silence, truculence; he cultivated an occasional brooding intensity. He had never been as stubborn as he was with her. (IV.15.31)
And yet, Alan has this admission to make:
This was the version of himself who spent six years with her. This version of Alan was fiery, jealous, always on his heels. He had never felt more vital. (IV.15.31)
Ruby might be a whole stack of crazy, but Alan can't seem to get enough of it…until she becomes just too much to handle.
We're not 100% sure how everything falls apart for the two of them, but we do know that Alan needs to help their daughter Kit piece the puzzle of Ruby together. It's a delicate process. Alan knows that he bears a lot of blame for the disaster of their marriage, and he doesn't want Kit to think that he's a hero or somehow more responsible.
But at the same time, Alan can't avoid the fact that Ruby really is kind of a horrible person. The problem? How to voice that without turning into a bitter person or making Kit unable to have a relationship with her mother.
It's another thing that drags Alan into a pit of despair:
The greatest tragedy about Ruby was that talking about her made him sound like a bastard. She had done him great harm, repeatedly—she'd torn him open, thrown all kinds of terrible ruinous stuff inside him, and then had sewn him back up—but Kit couldn't know that. (XV.28.103)
And why can't Kit know that? She's a grown-up who apparently wants Alan to tell her, truthfully, how to deal with her mother. She's pretty finished with her mom, but Alan needs to patch the relationship between mother and daughter. He has a fairly selfish reason for this.
He had to repair the damage. Alan didn't want to be the only parent. And he worried—or rather he knew—that if Kit could find her mother unworthy, then using the same tools of reassessment, she would find Alan unacceptable, too. (XI.42.76)
And it's not just that Alan's afraid that Kit will turn her critical powers on him. Repairing the relationship between Ruby and Kit is a classic diversionary tactic. If Kit focuses all her mental energies on figuring out what's wrong with her mom and how to fix it, she won't have the time to think about the relationship with dad.
While Alan's perfectly willing to admit that he had a big role to play in his family's dysfunctionality, he's still not willing to take the title of MDP (Most Dysfunctional Player) from Ruby. He's just not that heroic.