Dilemma: I’m in my early 70s, tight in my budget and worried about down the road. My husband and I had 23 years of a great marriage. We had no children but worked in our business together and I was devastated when he died so young. But that was many years ago.

My house has a small mortgage and needs work. My income is mostly Social Security with a little bit of extra income from what savings are left. I’m quite alone, and no one knows how tight I really am, as I’ve been able to keep up appearances.

I haven’t fallen in love with anyone in all these years, but now I’m starting to think financially. There’s a very nice, older single gentleman at my club who is always flirting with me. (I don’t look my age.) We’ve had a few dates and it’s been pleasant.

He’s very wealthy and all the girls are chasing after him, but he seems to have eyes for me and is looking for some kind of commitment. Do you have any advice for someone who is thinking of making a match for money? I know women who have done that, but it seems they’re miserable in spite of the big houses, cars and jewelry. It looks like a hard way to “make a living”. On the other hand, being alone and broke is not my idea of heaven either. I have little family and am fearful of being lonely, too.

It sure seems like a solution, but … Any advice?

Meg’s advice: That’s a really difficult question, and it’s oh so personal. Many people play the money card when choosing their partner, but there needs to be some clarity first. Take off the money goggles for a second and ask yourself this: Do you like him a lot? Admire him? Do you share values? Can you laugh together? Can you crawl under the covers with him easily? These days of Viagra can put another spin on an old story. Can you be good friends? Start there, and see how it scores.

Sometimes, a relationship like this can work like a charm. Other times, it’s a nightmare that’s hard to wake up from, and yet you may not know that until you actually make a life together. Please proceed with caution.

Here are some sobering thoughts:

Are you sure he’s wealthy? He may be looking for the same thing you are … financial security and his cash flow may be weak. Do some serious checking, since money is your incentive.

How old is old? If he’s got one foot in the grave, and you don’t mind caretaking, there may be an arrangement to be had. But it may not be as secure as you think, unless he sets you up financially in the beginning, and that’s a difficult negotiation, to say the least.

Does he have children? If so, your presumed financial security may very well be compromised, as most people are going to favor their kids financially. You can’t blame him, either. What would happen to you if he goes first? Are the kids nice and welcoming? Problem children can totally rain on any parade you’re considering. Consider this a big deal … and possibly a deal breaker.

Is he cheap or generous? You can usually tell that while dating. Listen up to what he says and how he behaves. Generosity is either in him or not. Leopards don’t change their spots, especially elderly, cheap leopards. That would take any bloom off the rose for me.

Don’t let romance (his) lure you into false promises. You need to understand his full intentions up front. It’s a business decision, after all, and he wasn’t born yesterday, obviously. Although your financial worries may turn him off, it’s better to know what you’re looking at up front then to get into a situation worse than you’ve got. I’d rather be captain of my own ship, even a modest one, than a captive on someone else’s.

Got a dilemma? Email askmeg@meggreen.com. Meg Green, CFP, is a wealth manager with offices in Aventura. Her Money Dilemmas column runs monthly in The Miami Herald.