Should She Stay, Or Should She Go?

I know what I think, but I’m curious what you would do in this situation.  You are middle aged and wanting companionship.  You find someone that is kind, funny, supportive, complimentary and attractive but their spending habits are horrendous.  (See below)

Dear Prudence,
I’m in my early 50s, and this is my first real relationship in about four years. Good men have been hard to find. I have been dating a wonderful man for a few months and enjoy his company very much. We have talked about spending our futures together. He is kind, funny, supportive, complimentary, and attractive. However, there are a couple of problems. He makes just a bit more money than I do, yet he is always broke and struggles to pay his bills and make house payments. He has terrible spending habits. For instance, he bought the entire clearance inventory of diamond rings at a low-cost store with the intention of reselling them on eBay, but he never got around to listing them. He buys junk at second-hand stores with the same intention and result. He has spent his employer’s retirement contribution every year and has nothing saved for retirement. He is also a packrat and a horrible procrastinator. His home is in dire need of repairs. He also has a small, old dog that uses his house as a toilet. I am careful about spending, and it makes me very nervous to live on the edge like this. Although otherwise I could see myself growing old with him.

—Worried Girlfriend

Dear Worried,
It sounds as if you may need that vast selection of discount diamond rings as a nest egg if you stay with this guy. Since you’ve known him for only a few months, stop talking about your future together and look at the present. On the plus side, he makes you feel great. On the minus side, he’s a broke spendthrift whose urine-soaked house is falling down around him. I know a good man is hard to find (and vice versa, as Mae West observed), so why not enjoy his company—at your place!—and leave it at that. Marry him, and you two likely won’t grow old together, but you will grow old with your debt consolidation company. Keep in mind this warning: The first time he suggests you loan him some money, even for the highly desirable purpose of steam cleaning his carpets, let that be a signal that it’s time to start looking for another man.

Personally, if I was single at 50 and met a woman with the above characteristics, I’d run away.  Because finances are important to me, I wouldn’t let another person pull me down in to their financial drama.  If this person is 50 and still hasn’t figured out how to manage his money it is doubtful that he ever will.  It is quite likely that if she ended up marrying him, her finances would slowly be torn apart as well.