A couple of readers asked me this one.
I answered via my e-newsletter that, yeah, the guy should pay the first time out, only because most men will assume you're politely giving them the heave-ho if you reach into your wallet.
Unfortunately, this means that men can shoulder an unfair financial burden. So, if you're out for the first time with a guy, and you like him, let him pay. Then look him in the eye, smile sincerely, and thank him. You can say, "What do you say we let me get it next time?"
This way, he knows you like him. He knows you are not taking advantage of him (a lot of men have been burned by women who feigned interest in an effort to score free drinks, for example, although I know for a fact you are not one of them).
If he likes you, he'll call you again (don't call him; you've made your intentions known). Suggest something affordable and pick up the check.
My advice solicited a question from another reader who said she went out with a guy she met on a dating site. As she approached the register to pay for her meal at an Italian buffet, the guy, who'd already paid for his, gave her an annoyed look. He asked her if she expected him to pay.
She said this pretty much 'screamed' to her that he didn't like her even before they'd eaten lunch. She asked if I agreed. I agree. It's possible that he was protecting himself from being taken, but come on. What a turn-off!
And if he ever called again, I'd tell him thanks but no thanks.
If a guy's hitting dating sites and meeting several new women a week, it's going to get expensive if he pays for meals. If you agree to meet a fellow you met online, save yourself the trouble of a potentially awkward situation. Suggest you get together for coffee.
Then, if he turns out to be a graceless jerk who balks at paying for yours, tell the clerk you'll take it 'to go.'