Before measuring his ring finger, ask yourself: Do I really like him?

Dear Carolyn: I'm a 44-year-old, divorced woman and I want to get remarried. I've had a few fun dates with a 48-year-old, never-married man. We've not yet talked about previous relationships or goals in our relationship. We've all been warned to be leery of never-married men; it's likely they never will get married -- right?

What are your thoughts on the matter? As I move forward in the relationship, what are some questions I might ask of him to learn whether he is truly open to commitment or if I'm just wasting my time?

Dear Reader: The never-marrieds are a bad risk because they will never commit, yes, I've heard that.

Remember, too, that divorced people will commit -- but then they'll bolt. And of course widows and widowers will always remain devoted, on some level, to the departed, whom you can never hope to replace.

I hardly need mention the ones who are dating you while they're still married, but I will, anyway: You can never trust them not to cheat on you the way they did on your predecessor.

I'm not sure if the spouses of alien abductees are considered married or a category all their own, but, either way, they'll just be up all night checking the foil on the roof.

And don't get me started on the marriage-or-bust crew.

By my count, that just about rules out dating another human being.

If you're at peace with the idea that a certain level of risk is inevitable, though, then there are arguments to be made for and against just about anyone in any of these categories. That's why the most important questions you can ask this man are the ones that help you get to know the one you're dating, as a person (as opposed to a spouse-by-numbers). Find out who he is, what he stands for and whether you'd ever commit to him.

Dear Carolyn: This is a twist on a common problem:

My new boyfriend makes more money than I do. We take turns paying when we go out. Unfortunately, he has expensive tastes. I tend to order frugally; he orders, basically, the priciest things on the menu.

We've discussed our income disparity before, and resolved to eat out less. But when we do go out, again, it's always something that costs twice as much as what I ordered! I feel like a cheapskate for being annoyed, but I have serious money problems as it is and I'm very stressed out about them.

So how do I say, "Baby, get a burger, not the filet mignon, because I'm going to get evicted otherwise"?

Dear Reader: Common problem, but there is no twist: You need to learn to say no.

It's not a matter of the words; your "Baby ... " line is just fine, and you could also suggest splitting things equitably. Though I would argue that you need to speak up even sooner than that, and offer dately reciprocation by cooking and not dining out.
The real issue is your ability to say the words. This is your money he's spending, to the detriment of your financial and emotional health, and, since you won't stand up for yourself, he's doing it with your permission. Find your spine, and use it.