Ah, money and dating: the question of who pays for what (and how much) can be a contentious and uncomfortable matter. Does it matter whether or not he grabs the bill on the first date? How far into the dating cycle should you be before you have a discussion about money? Are there any men to watch out for, financially speaking, when you're single and looking?

I took these questions to Nancy Trejos, a personal finance columnist for the Washington Post and author of the new book Hot (Broke) Messes: How to Have Your Latte and Drink It Too.

Who should pay for the first date?
Everyone's conflicted about this. I have female friends who feel uncomfortable when the guy pays for them on the first date but I know others who expect it. If you happen to be someone who believes the guy should pay for the first date, that's fine, although I'd offer to buy him a drink afterward. If it makes you feel that you owe him something in the end, then pull out your wallet.

If the guy doesn't pay for you on the first date, is that a bad sign?
Not necessarily. If he doesn't, and you're trying to figure out what that means, try to put it in context. Think about his financial situation — and how much money he's making, for instance.

Still, I think that in most cases, if you're not sure how a date is going and then the guy suggests you go Dutch, it's almost always a bad sign. (If he takes you up on your offer to split the check, it's harder to read.) Anyway, in terms of financial status, is there a certain kind of guy you should never date?
You don't want to immediately write off a potentially decent guy because of the kind of car he drives or what he does for a living. That said, you do have to watch out for someone who's not willing to be generous in the beginning. Nice gestures don't have to be expensive. He could give you a bunch of tulips or cook you a nice meal.

Should you steer clear of any guy who is in debt?
No way. Everyone has some sort of debt, whether it's a student loan or the AmEx bill that you haven't yet paid off because you didn't get your reimbursement check or a mortgage. If he's honest about any financial difficulty he might be in, and he's dealing with it in a responsible way, that's probably okay.

Fair enough (though I myself would consider it a big red flag if I met anyone who was deep in credit card debt). What about a big spender? Is it fine for someone to throw around money as long as he has a big job — or a big trust fund? Or might that be a danger sign that he's reckless about finances?
If he's flaunting it, it might be a sign of hubris. But if he's just spending money because he can and it's within his budget and he wants to be generous, then there's nothing wrong with that.

After you start dating someone, how soon should you start talking about finances?
When you're spending most of your time together and you feel like there's long-term potential. Definitely don't do what my ex-fiancé and I did: We moved in with each other without really knowing what kind of shape the other person was in financially. That's ridiculous. Once you get serious, you should discuss how you're going to split expenses.

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Lovelies: Do you have any stories to share about dating and money? Do you have any horror stories, like I do, about guys who scribbled down the different things we ordered on a napkin, once the check came, so he could figure out exactly how much each of us should pay?

What Do You Think?