You sound exactly like a spoiled upper crust brat! Go to your country club and find a male jerk like you.  You two will deserve each other. Your boyfriend's father was a hard working middle class guywho lst jobs but managed to hold his family together and did his best to support them.  You think he was a failure.  What a snob!  You don't deserve a good self made guy like the one you are with. Do him a real favor and get out of his life.  No one will ever measure up to ypur "rich daddy". 

I'm sorry that you did, as you predicted, get a slew of "oh, you're rich, how dare you be anything but humble and grateful" responses.  People seem to think that if you are rich, you have no right to complain or acknowledge distress in any area of life, even ones that have nothing to do with money.  For instance, I read an article recently about a rich family who was slammed for expressing grief over the death of a family member--as if daring to be anything other than deleriously happy all the time is a form of arrogance if you have money. Being called a brat or having your situation compared to liking someone's feet is ridiculous and not helpful, with all due respect to the responses.

It is intelligent and certainly relevent to explore the assumptions about money, work, safety, and responsibility that arise from different upbringings; it will affect your relationships with other family members on both sides, how you raise children, and what you expect from each other.  It doesn't have to cause problems if you are able to talk about it without defensiveness--to see that difference does not mean deficient on either side, and that everyone develops some kind of assumptions about the world depending on what they grow up with.  Assumptions may be right or wrong, and it's fine to explore that--in fact, if you do it in a spirt of openness and curiousity, it can bring you closer.  Discussions like "I will pay more for things of high quality because it's a good investment" vs. "It's important to spend the least amount of cash possible, because you never know when you might need it and it will be gone" are basically about class assumptions based on life experience. 

Also, you don't seem to come from generations of wealth, and so you might see more commonalities between your husband's family and your parents or grandparents than you do between your perspectives and his.  In fact, you sound like you found a man whose work ethic is similar to your father's.

If you think this is worth more exploration, you might look into some short-term therapy with a therapist who is knowledgeable about class issues and who has experience working with the children of the rich.  If you Google "children of the wealthy" there are also some interesting articles out there--one in the Atlantic from last year, I think.  It's also worth doing because presumably you will be raising some children of the wealthy yourself, and it's good to know what might be involved.

I hope you don't take the nasty responses to heart.  Having enough money leads to more happiness than not having enough money, but beyond a certain point--certainly well below where it sounds like your family is--it doesn't continue to bring more and more happiness.  In other words, people who are very wealthy are about as happy as people who have enough money to cover their basic needs plus some extras--not more.  And the stress of life comes to everyone.

The think that stuck out for me, above all else, was that the letter writer thought that her boyfriend's father had been irresponsible because he was in and out of work. She is going to be very close to her in-laws when she marries and I wonder if she realizes that it will not be possible for her to feel close to them if she doesn't even respect her husband's father. You don't just marry the man - you marry his entire family, for better or for worse. I think it is terribly important and a bell weather for other things that you like and respect his parents and family members, at least, the parents.

My own mother grew up quite affluent with a live in maid and gardener, etc. She attended Radcliffe College for graduate school during the Great Depression, etc. She married my father whose dad had already died: He, my father's father, was a boiler maker and his wife was a former maid, a servant, till she married, but guess what,my Dad went to MIT on scholarship and my mother loved his family and understood that they were Irish immigrants who were working their way up. My mother lived, as you did, a life of privilege growing up. Part of that privilege was knowing that it is the character that matters most, and mutual values and beliefs and respect. They had a very happy marriage, a wonderful marriage. My father and mother respected each other and cherished each other. Never for a moment did my mother ever worry that my father came from a less affluent family. Never!

Maybe some personal couseling is in order to sort through your conflicted feelings about your relationship to this man. It sounds like you need to figure out and reconcile the role of monetary wealth in your self-identity and personal values, and how this may play out in a marriage. I don't think it is fair to yourself or to any man you might marry to leave these conflicts unresolved.