Check, Please, Part 2


by The 4-Way Panel

Dear 4-Way,

I’m a single woman in my late 30s, which means I’ve been dating for about 20 years. Over the past few years or so, I’ve noticed that when men ask me out, they expect me to pay for half of the date. I’m all for offering to chip in on later dates, but I’ve kind of always gone by the rule that for a first date, the asker does the paying. Am I being ridiculously old-fashioned? Does it mean something if they ask me if I want to split the bill with them—perhaps they’ve already decided I’m not worthy of a second date? If I ask a man to have drinks or dinner with me, I expect and intend to pay, though about 75 percent of the time, he won’t let me and he ends up paying. I have girlfriends who are more rigid about this than me; they never offer to pay. Who’s right?—DR

Rebecca    The straight woman’s perspective: Rebecca Brown

I wish I smoked right now. Because I’d take a nice long drag on an unfiltered Marlboro, maybe take a couple of shots of Wild Turkey, and then in my best gravely, veteran-dater voice say, “Oh, honey, don’t I know it!” I struggle with this question all the time. I feel like I’m the least equipped of the four of us to give you sound advice since it sounds like we’re in the same dating space, but here goes. I agree with you: The asker should pay, regardless of whether the asker is male or female. But for whatever reason, I don’t do much asking, so to be fair, I try to suggest something that’s checking account-friendly for everyone when making plans.

But I have a horrible confession to make, one that I’m sure will mortify my other 4-Way compadres as well as any woman who considers herself a feminist and modern woman. I secretly hope that they’ll pay on a first date. (What’s that rumbling noise? The women … are … coming for me! And the men too!) I absolutely believe that women should have all the same opportunities as men, and this—for better or worse—includes paying for dates. But not a first date. Sorry. I’ll probably get angry email for saying this, but there it is.

I really appreciate the gesture of someone who wants to treat me to something that he thinks we’ll enjoy doing together. There’s no rule that says people have to drop a ton of cash on dates. I eat just fine on my own; I don’t need an expensive dinner. What I would love is to enjoy something interesting and fun that exists outside the “let’s have dinner” box with this new person who’s got my heart racing. It doesn’t have to cost a lot—we could have a picnic, go to an art gallery, or even get some cheap bleacher seats for a baseball game (truly one of the best places to get to know someone).

I also don’t think it means there’s no interest if he or she asks you to split it. Asking someone to pay is essentially them putting their beliefs on the table—“I don’t think I need to pay for all of this”—and unfortunately for that person, you don’t agree with that particular belief and probably won’t be in a big hurry to go out again. My advice to you—and to all of us who are confused about the payment issue out there—is to get a little more involved in the planning. Suggest something fun and affordable so if you end up paying, you’ll have a good time no matter what and won’t feel miffed for spending $50 on some overcooked lamb and a dud of a date.

Check in tomorrow for the straight man's perspective by Chris Kennedy.

The 4-Way is published monthly. If you have a question for our 4-Way panel, please send it to them in care of the editor at To read more of The 4-Way columns or to listen to our podcasts, visit The 4-Way now.

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