Gentlemen Speak: 4 Steps to Avoid That Awkward ‘Who Is Paying for This Date?’ Moment

Follow these steps to keep the end of your date free from awkward moments.
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Follow these steps to keep the end of your date free from awkward moments.

I have a plan when it comes to paying for dates. If I initiate the date, I pay. The way I see it, if they don’t have to pay for anything, they’re more likely to join me, enjoy it, and be glad they went. I tend to be the initiator on the vast majority of the dates I go on, so this system of paying for the drinks or meals I initiate goes a long way to prevent any awkward uncertainty. I’ll let her order first, and I’ll make it clear to her that I’m paying, which can be as simple as, “This is on me.” When the bill comes, I take it, and I pay for it.

The trouble is, not every guy has a plan, and as a result many women dread the awkward end of the date—that moment when the bill comes and they don’t know whether to go for it or not. And what does she do when it’s not clear she’s on a date? Or when the guy isn’t proactive or clear about how to handle the check? Do you wait for him to pick it up? What if you just want to get the hell out of there? If the woman takes the bill, might a man interpret that as if she will pay for the entire bill? And what if he is quick to pay for her meal as well as his? Does that mean he’s expecting some sort of payback in the (near) future? Who knew something as innocuous as a restaurant bill could cause so much trepidation and awkwardness.

Which brings me back to the plan. Everybody should have one, especially dudes. But because many of them don’t, it wouldn’t hurt for women to have one, too. So here’s one man’s attempt to help women navigate the uncomfortable question of, “Who’s paying for this date, anyway?”

01. Make the first move.

If you’re a woman, even one who prefers and even expects a man to pay for dates, act as if you were planning to pay all along (even if you weren’t). If you’re ordering at the counter, order first and pay for your order. If the guy is a gentleman and wants to act as such, believe me, he’ll interrupt and make sure that he pays. Then if he doesn’t, there’s no awkwardness. And please, by all means, if he hasn’t indicated that he’ll pay for yours, and you don’t plan to pay for his, don’t step aside to let him order on the same ticket.

02. Go for the reach.

If you’re at a sit-down restaurant, and your waiter has any couth, he or she will present the check to the man. But even so, I recommend that you still reach for your purse when it comes time to pay, as if you were planning to pay all along (even if you weren’t). Again, if the man has any sense, he’ll stop you right there and offer to pay. And if not, you’re in a perfect position already to follow through and pay for your part.

03. Don’t protest too much.

If you’re from the Midwest, like me, where people are expected to deny gifts once, twice, or even three times (I’m not even kidding) before accepting, I’d recommend saying something like, “Oh, you don’t have to pay for me.” But don’t feel like you have to say that, either. You should be sure to say thank you. If you don’t, it can definitely come across as if the man were under some sort of obligation to pay for you, which can kind of ruin it—or even really ruin it.

04. Meet in the middle.

In the most-awkward-possible situation, when the server puts the bill on the table, but your date doesn’t make a move to grab it and you just want to get out of there, it’s perfectly legitimate to say something like, “Well, this has been really nice. But I do have to get going.” If he still doesn’t grab the bill, open it in such a way where it stays in the middle of the table and it’s visible to both of you. Put your preferred method of payment on the table (not on the bill itself), and if the server comes over, tell him or her that you’d like to pay for your meal.

Remember, these are tips to navigate around an awkward situation, not a guide as to how I think paying on first dates should go. If it were up to me, all men would follow my philosophy and never have to make their dinner or drinks guests wonder who has the bill.

While sometimes I’m tempted to think the worst about people, especially men, generally speaking most men are more clueless than they are selfish, chauvinistic pigs (although there are plenty of those, too). The truth is, most men who give off the awkward “Who’s paying? I don’t know” vibe probably have no idea what they’re doing, both on that particular date with you and with dating women in general.

As with anything else in the weird world of modern dating, especially when it comes to first dates, my best advice is to keep an open mind. Give people the benefit of the doubt, and don’t take any of it too seriously. Who knows, that dude who seemingly has no romantic skills might end up being the man of your dreams, and he just needed a little nudge on the way there.

Photo Credit: Manchik Photography