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[quote=Anonymous][quote=Anonymous]OP here. I'm a little shell shocked here. First off, my daughter's college is not an issue. She has a college fund, and a father with so many assets that any CSS profile makes her ineligible for aid. UVA uses the CSS in addition to the FAFSA anyway. And all her other schools are private. Secondly, my kids have a rich asshole dad and my divorce agreement protects them for life.

I'm with this guy because he's loving and kind-- yes too generous-- but not the kind of asshole my workaholic arrogant narcissistic ex husband was.

Lots of men are financially devastated by divorce. That doesn't mean they deserve no future. After eight years single I ran across all the types of single men in their 40's-- the losers, the scam artists, the impotent ones, the misogynists, the control freaks, and the fundamentally broken.

This guy is not that. He does all the cooking, all the cleaning, takes me to doctors appointments, loves my disabled son way more than his own dad does, and is supportive of my career and nice to my family. In addition, his income is 4x what mine is.

Yes, he needs to learn basic financial skills, and his dynamic with his family of origin is clearly fundamentally problematic. But so is mine. My mother has borderline personality disorder and my father comes from a long line of alcoholics. People come with stuff-- it's what they do with it that counts.

So the advice I was looking for was how to work together to establish boundaries and protect us from them.

FWIW we had already decided not to get legally married because living in a high cost of living area, the SALT CAP means our taxes would go up $8K annually by getting legally married. We are getting married in a church, which is what I consider marriage.

I do appreciate all the concerns and red flags-- trust me, I have been with that guy before- the user and loser. But this guy is better than that. He's just imperfect like all of us. 
[/quote]

So much to unpack here.

You clearly went from one extreme to the other. There can be a happy medium.

You are not responsible for providing the happy future for this guy, no matter how nice he is.

The fact that your family of origin has issues does not mean you have to be with someone who also has issues. You aren't broken.

What's the plan for when he stops working? What's the plan for if he has to stop working before he wants to?

When you say he makes four times what you do, can you be more specific? If you make $250K, for example, then this guy is making $1M a year and can't figure his life out and has no savings. [/quote]

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