Dear Moneyist, Please do not hammer me for presenting this idea. I understand many people feel strongly about the meaning of marriage. I dated a guy for a couple of months, but we agreed to just be friends. He wanted to continue to date, but respected my choice. Over a couple of years, we have gotten together monthly for dinner and have enjoyed a great friendship. He is a major introvert, has a long career at the National Security Agency, has few friends and has never been married (no kids). He asked me to marry him, so I would receive his Social Security in addition to his health-care benefits. He has made the case to me over several meetings. This past November he was diagnosed with Stage IV lung disease, which has metastasized throughout his body. He has been told the median time frame for him to live is 6 months. I have helped him with doctors, went to an appointment with him, and remain as a close support. He has asked me to be his estate trustee and I agreed to that. He is upset that the portion of his pension that the government contributed to over the last 30-plus years will be “lost.” He asked me to marry him, so I would receive this, in addition to his health-care benefits. He is clear-eyed about this and has made the case to me over several meetings. Also see: I’m 65, my mortgage is paid off and I have $370,000 in savings, so why I am still worried about money? [1] I am 62, work hard at a modest career with a huge commute, put away 30% each paycheck into retirement, and have been divorced and have never intended to remarry for any reason. My financial independence has been hard fought. I have job security for at least five more years, but my retirement will be quite simple and a bit of a struggle. He has always tried to help me, but I have not wanted to muddy the waters of our relationship. I continue to date other men, and he has dated other women, some of whom I have met, but I do not have a boyfriend. Recommended: My husband asked me to file a joint tax return without telling me he owes back taxes[2] Is this ethical receiving government benefits in an arranged marriage? What if he recovers ? If I were to accept, is this money-grabbing on my part? Is this just his way to bring me closer? What other parts of this dilemma am I missing? I have shared this with a couple of close friends and they have made strong arguments for both sides. The proponents feel that this is just a financial decision. Those against feel it is unethical to essentially marry for money. I am leaning towards not...

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