This is a guest post from Early Retirement the Middle Way, who writes about her quest for financial freedom alongside living a consciously cool life.

Do independent, modern day women have it easier or harder in relationships? Are men threatened by smart and successful women? Are women having a hard time with traditional stereotypes? Is it difficult to be in a relationship with a man who makes less? Both women described below are real people. I have changed their details to protect their identities.

A:

A is a very successful entrepreneur. She is living with a man (also a successful entrepreneur) who for all intents and purposes, is her husband but he doesn’t want to get married. There is a contract in place stating that should they part ways, she is to leave and not have a claim on his house. They recently celebrated the birth of their first child.

A’s assets include her business and her vehicle. She lives in “his” house and pays him rent as he owns the building she runs her business out of. A has very high cash flow.

A feels lucky that she is doing so well in business because she knows that there is no way she could ever approach him for help financially. Her goal is to buy herself some rental property so that she owns real estate and has an alternate source of income.

B:

B runs her own business. She is married to a man to believes that you keep what you make. Thus he insisted on a prenup which states that he is not responsible for any debt that is not his and that B has no claim on the matrimonial home until they have been together for 20 years. He doesn’t do a whole lot for the household. He feels that providing a roof over B’s head is enough. He knows that by the end of each month, B has little wiggle room financially but will not offer to help.

B’s assets include her office building and upper level apartments which is co-owned by her husband. B’s cash flow barely keeps her above the poverty line with a surprise pregnancy and purchase of a building all happening in the same year.

B feels that her husband is just “old school” and that he has every right to want to protect his assets. Her goal is to pay off her debt (six figures) so that she can do whatever she wants.

Both women love their respective partners.

What advice would you give to each of the women described above? What are the real underlying issues here — financial and relationship?