Sheesh, the only question I’d have is whether Hallmark made a “and you thought you married up” line of cards that I could send to the Ex.
I wish I didn’t have to work ever again. 
There’s got to be something between working 70 hour weeks and not working at all. Why can’t he work a regular 40 hour week, contribute his small, but non-zero check to the household and live happily ever after? He’s not sponging off her. There might be an imbalance, but it isn’t as if he’s doing nothing.
Why not take a smaller amount rather than 3 or 4 million, so he can go to college and change careers or whatever?
Any self-esteem issues are likely to exist whether he takes it or not.
Otara
The OP deliberately doesn’t specify how expensive Diane’s life is, but I can’t imagine she lives cheaply. She grew up rich, after all, and it’s pretty clear she has no idea what a working-class salary really is. Anyway, my point is that I’d not be surprised if she fritters more in a month than Jack makes in a year. If that’s true, his contributing a nominal sum won’t make things better for him; it’ll make it worse.
Which is not to say I don’t think Jack needs to get over himself. As my little sister is fond of saying, he needs to grow up and get counseling.
Otara, are you taking about Diane’s self-esteem, or Jack’s?
Jack isn’t being sexist, since many modern women would also dislike this scenario.
Personally, in Jack’s shoes, I’d ask the lady if she minded me following the drachillix suggestion outlined above.
It’s hard to hate your job when:
- you’re your own boss and
- you’ve got money
If Jack went the drachillix route, he’d also be able to say he was working for the money, or investing it for her, rather than being a mooch.
“Stealth”? That was about as stealthy as the dude who went down on a knee in the middle of a packed Chinese restaurant…
Both really, but I was thinking mainly of Diane.
Otara
This little ditty about Jack and Diane - are they two American kids doing the best they can?
John Ellesar Mithrandir Aragorn Cougar Mellancamp has already been addressed.
Oddly enough, I know a couple in real life who somewhat fits this. At the end of the post I’ll let ya’ll know how it worked out for them.
I’d tell Jack that, given they’ve had a relationship for some time and she seems entirely sincere he should take her offer. He knows he’s not a gold-digger. I would urge him to NOT get greedy and put a little away for himself because no relationship is guaranteed, and of course, Something Tragic may occur to his girlfriend, but by all means take her up on her offer to go back to school, or for 4 million (which could actually last a lifetime if you’re prudent and frugal). Jack is getting older and he won’t be able to do manual labor forever. There are worse things than, essentially, marrying into money and it sounds like he won’t have to worry about in-laws.
As for my real-life friends - he was working in a factory, she had a high-end job in the medical field. After a couple of years of relationship he quit his job and moved in with her. She paid for him to get a commercial helicopter license. They got married. Last I heard they were still together and happy. As a bonus, he now is making a living flying helicopters, which he had wanted to do for something like 40 years but never had the money to do, and a new profession so he’s in no way a “freeloader” or just living off her.
A friend and I occasionally have discussions about what we’ll do if either of us hits the big lottery. If I win, she’s not sure if she’s willing to allow me to completely support her (although she has agreed that she’d be perfectly willing to share living space in the mansion I intend to buy). On the other hand, I have no problem with being her “kept man” if she wins. Of course, this may have something to do with the fact that I’m retired and am already living a life of (relative) ease while she is still working.