Gentlemen Speak: You’re Not Wrong for Wanting Him to Pay on a Date - Verily
Your instincts are spot-on.

For the past year and a half, I have been working for a winemaker on a vineyard in Virginia’s Shenandoah Valley. I’m telling you this so that you can imagine the sheer number of first and second dates I have witnessed in that time. Wine? Activities? It’s a dater’s dream.

Guys still generously pick up the tab every once in a while, but it’s less common than you might think. Often, I see fifty-fifty splits on the bill. Occasionally I’ll see a woman slink off on her own to covertly buy a couple glasses at the bar for the two of them, and then he’ll cover the rest. The lack of consistency has left me wondering if the standard script of men paying for first dates is harder to find than certain rare bottles of wine.

I think that now, with the emergence of so many dating apps and more frequent first dates, guys are less willing to cough up the cash on dates. My female friends are none too pleased by this trend. Still, they wonder whether their instincts are correct or if they’re just holding on to an old-fashioned dating tradition that is easier on their bank account. It’s not like they’re going to cross an otherwise nice guy off their list, but they feel guilty for expecting (or even wanting) a guy to pay. So, they always anticipate splitting the bill but wish the old-school expectation for guys to get the first date tab would reemerge.

I get that finances and budgets are at play here. And I hear the arguments for equality and fairness. If the guy isn’t jumping at the check, I don’t blame you for reaching, and I think it’s cool to give him the benefit of the doubt. But if this is off-putting to you and maybe even a red flag, I can tell you, from a guy’s perspective, that you’re justified in feeling this way. Here’s why.

He Wants to Take the Initiative

I’ll let you in on a little secret: Guys want to be the one who sweeps a woman off her feet. To men, this means asking her out, planning the date, and covering the bill. A recent survey conducted earlier this year by Time shows that 85 percent of men still think they should pay for the first date, topping the 72 percent of women who thought the same. The simple fact is, men still want to treat the women they like.

One of the best dates I’ve been on recently was also probably one of the most expensive because it included tickets, drinks at the event, dinner later, and drinks later, too (all in the city). The funny thing is, I actually can’t remember how much I spent, and I couldn’t care less because my date told me how much fun she had.

Whether it is a date that emerges from an app, a chance meeting, or a longtime friendship testing the waters, if the guy takes the initiative to ask you on a date, then he should also take the check. If he doesn’t, I would call that a red flag. Why? Because it might mean he’s not super into it.  As a friend told me recently: “When I ask a girl on a date, I am trying to win her heart, so of course I am going to pay for dinner or drinks or whatever we decide to do. It’s not about the money. It’s about the time we get to spend together getting to know each other.”

Taking the initiative isn’t about getting the upper hand in the relationship or about who has the biggest salary. For a guy, taking the initiative means that he is willing to put himself—feelings and all—on the line for you. And, on that note, if his picking up the check feels like a sign that you then owe him something, that’s an even bigger red flag (for the record, you don’t). He should want to show you that spending time with you holds value for him. If you are feeling guilty because you aren’t paying for part of the date, it’s OK. Tell the guy how much fun you are having, and your words will mean more to him than you can imagine.

It Makes His Intentions Clear

There is also a very practical reason why men paying for the date is still a good thing. When I pay for the entertainment, dinner, or drinks, it sends a clear message of my intentions. This is not a friend date or a networking event or a “hangout.” This is a D-A-T-E.

Some might call it chivalry or just plain good manners, but footing the bill on a date gives context to the evening and a certain amount of romantic vibes. When we asked the Art of Manliness’ Brett McKay what chivalry meant to him, here’s what he had to say:

“For me chivalry consists of small courteous acts displayed by a man toward a woman that serve as a symbol for the differences between men and women. Chivalry is not about either the inferiority or the lofty superiority of women. Instead, it can foster mutual respect and remind us of our underlying biological differences and the complementary nature of the sexes. These little social gestures add some texture to a social life that often feels bland and homogenized.”

Many of us have experienced a dating scene that feels, as McKay said, bland. Without those gestures (a door held, a seat pulled out, a check paid), what sets a date apart, truly? Good conversation and a round of drinks can be had with any friend of your choosing. Allowing the guy the gesture of paying the bill can add those layers of meaning we are all longing for. Don’t feel bad for expecting that.

So while expecting the guy to pay for the date may seem old-fashioned to some, don’t worry about it. In this era of endless casual drinks that lead nowhere, we could use a few more signs that say, “This means something.”

Photo Credit: Erynn Christine Photography