It’s as awkward as a sudden pimple breakout. Or realizing you tucked your skirt into your underwear. I’m talking about that inevitable time when the check comes. You’re on a date. Things are going well. Then the waiter approaches and drops off the bill. You both look at each other. You both think to yourselves. What now? Who pays?
Now, at this uncomfortable juncture, one of three things occurs. First, you can pretend it didn’t happen and continue to chat, thus prolonging the awkwardness and the inevitable payment. Second, you can stare at it, hoping the other person throws down their card, while you pretend to ever-so-slowly reach for your bag and wallet. Or third, you can excuse yourself to the bathroom, and never come back to the table.
What’s the RIGHT thing to do? What are the rules for who pays?
Here’s what I think. Men should pay for the first date. End of story. It is their responsibility. It is their birthright. It is their job. It is just what men do instead of having to wear 4-inch stiletto heels or beautify their faces with makeup. Ladies, you should cut a brother some slack and, at the very least, pretend to reach for your purse or wallet, because that is polite. It might be 2010, but some things just don’t change. Simple, right? Yeah right.
Now, I’m sure this position angers some guys. They’ll complain about how this isn’t fair. You know what?? LOTS of things in life aren’t fair – and that accounts for 99.77% of men’s lives (including losing their hair an average of a decade faster than women). Real men know this is true and they simply don’t care. And any man worth being involved with will see and accept that the field is tilted, and that it sucks, and then, regardless, dive in enthusiastically with both feet – or else he won’t ask for a date in the first place.
At the end of the day, first impressions are important. We all know that. Hence, it’s smart on the first date for the guy to make the first move when the bill comes. This goes not just for the very first date, but throughout the early stages of the relationship. It is not only the gentlemanly thing to do, it also indicates that you are responsible, steady and chivalrous. We, women, like that. Let me repeat. We, women, LIKE that. It helps us to determine whether or not you are relationship-ready. Men set the tone during the early dates for a potential future relationship.
Thus, men, you should just bravely endure, pursue, and woo. All that being said, pick a restaurant that you can afford. Better yet, buy a bottle of wine and invite me over. And if you really want to make me swoon … cook dinner for me. MAJOR POINTS. And sometimes, I will offer to pay. Because I can afford to pay for my own dinner and even yours sometimes. I really don’t expect you to support me. I only want to know that you are a gentleman. That you can take care of yourself. That you are generous. That your mother raised you well. And that we can sit across from each other for a few hours without checking our vibrating BlackBerries and just enjoy each other’s company. Truth-be-told, at the end of the day, I don’t really need the truffle mac n’cheese (although it is undeniably delicious). I just need to get to know you.
Here’s the thing. There’s a reason sites like grubstreet and newyorkmagazine exist – because they give you information on inexpensive starter restaurants where two people can test each other out either in front of a fireplace, at a BYOB, or listening to live music, before graduating to a nicer dining establishment, like something on the Michelin guide. It doesn’t really need to cost a lot to take a woman out. Guys, I honestly don’t want you to break the bank dating me. And this is totally coming from a serious foodie. I have had the fortunate pleasure of having a few very generous men in my life who have taken me out to great restaurants. And yes – I loved every bite of my pasta sampler at Babbo. But that’s not what made the relationship work or sustain us. What I really enjoyed was the good company.
Bottom line? Some of the best dates I’ve ever been on have barely cost a cent. A first date making matzoh-pizza during Passover and chatting for hours over bottles of red wine. A long run along the east river and watching the sunset while learning how to skip rocks. Cheap falafels in Park Slope and a cold lager at the Brooklyn Beer Garden. A long hike followed by homemade Bloody Marys on some folding chairs in the sun. All of these dates were great dates. Perfect dates. And they were inexplicably more memorable than the countless fancy dinner dates I’ve been on.
Guys, it’s really quite simple when you break it down. You should pay. But it doesn’t need to be expensive. Treat us to something. Be confident that you have a lot to offer us. Be creative and respectful. Because that costs nothing.












I agree that a man should pay sometimes, but I don’t always agree with that and I’m sure that there are other women out there who may disapprove too :p Some women view the man paying for the date as egotistical and old-fashioned…in today’s society it doesn’t seem weird for a woman to pay or even for the bill to be split. Or if one decides to pay the bill and the other the tip, or for one to pay for dinner and the other for dessert. Whatever the case may be, times are definitely changing.