WalletI feel like a traitor to my feminist values to admit this, but I expect the guy to pay for the first date. I know, I know!  That is the lone issue about which I’m a traditionalist and perhaps it comes from my father.  He has taught me myriad important lessons: respect for nature, how to ride a bike, and that men should always pay for the first date, no exceptions. My dad is a true product of the 1950′s and he has long instructed me to leave my wallet at home when I go on a first date (not figuratively—literally don’t bring any cash because the man should pay and that’s that). While I agree with my dad, I’ve chosen to ignore his suggestion and show up on first dates with my wallet … just in case.

Recently, I went on a date with a handsome fellow Brooklynite. He had arrived on foot to the date since he lived nearby and it was an unseasonably warm evening (note that he walked, so didn’t have to deal with a subway pass or cash for a cab—store that tidbit away for later). We had planned to meet at a local bar of my choosing, but there was a private event at that venue, so we walked around a bit and ended up at my favorite Italian restaurant and wine bar. We sat at the lovely marble bar and ordered wine (by the glass). I suspect that neither of us wanted to order a full bottle and strap in for the potential hour’s worth of stilted conversation with a stranger we weren’t sure if we liked yet, so we took it glass by glass, which adds up quickly. After quite a few glasses, he suggested that we split an entrée and I rolled with the punches even though I wasn’t especially hungry.

Conversation was good, but I wasn’t sure whether or not a second date was in our future, so when the check arrived I was going to see how he played it and, against the rules of my dad, I was planning to offer to pay for half. In my sophisticated and somewhat illogical hierarchy of principles, letting a guy who I’m not sure I’m interested pay for a first date is a worse offense than a guy I am interested in not offering to pay for a first date. I just never want to take advantage of anyone and that’s how I’d feel if I had let him pay for everything with no assurance that we’d see each other again. So in this instance, I was ready and willing to go Dutch.

The check arrived and I began my elaborate routine of digging through my purse to look for my wallet while waiting for him to stop me because he’d inevitably insist on paying. That’s just the dance of the first date. But I truly wanted to pay for half, so I’d offer that and insist and we’d see where the chips fell on the floor of this wine bar, so to speak. My purse digging routine went on for a while and he said nothing to shoo me away from searching for my wallet. Rather, HE spent an inordinate amount of time digging through his jacket pockets and emptying their contents onto the bar: his apartment keys, his iPhone, his ear buds. Each item was carefully and deliberately pulled out of the pockets as though he were a prosecutor presenting his evidence to the jury. After this display he uttered something that sounded a line of dialogue from an unconvincing actor,“Huh…well I must have left my wallet at home.”

“Oh my goodness! Did you lose it?  Can you remember when you last had it?” I reacted with enough emotion for both of us, as one normally does when one’s wallet is suddenly missing.

“I had it at my apartment before I left … I’m sure I did. I must have just left it at my apartment. This is embarrassing,” he said with suspiciously flat affect.

I squinted my eyes and stared at him as I attempted to read the situation.  I wanted to give him the benefit of the doubt and assume that he was an honest person who had genuinely, accidentally left his wallet at home. After all, he had walked to our date so the facts lined up that he wouldn’t have realized his wallet was missing until now, $100 worth of wine and food later.

But the no-nonsense city gal in me chimed in, Come on, Selena—isn’t it convenient that he “forgot” his wallet? You’ve seen “Dirty Rotten Scoundrels,” so you know that some guys manipulate situations like this to fill the pawn with self-doubt in order to get what they want.  In that movie it was much bigger scores, but with this guy it would seem to be a few glasses of wine and dinner. Don’t be a fool–he’s a mooch, a grifter, and you’re just a pawn!

But he was so well-dressed—surely his finances weren’t so tight that he needed to hustle ladies for free drinks and food. Look at that starched, dry cleaned collar!  Or was that part of the manipulation? Dress like you’re a classy guy who has money, then the story that you simply “forgot” your wallet carries more weight.  I was so torn!

As these two lines of reasoning volleyed back and forth in my head, my date sat there and remained stunningly calm and matter-of-fact about the whole thing.  I wanted to give him notes like a film director to an actor, Listen buddy, if you’re going to use first dates to score free drinks and food, ya might want to SELL the whole “forgotten wallet” schtick a bit more. Just act more shocked and nervous—like how you would act if you had truly had forgotten your wallet. OK?  Great–let’s try it again, but this time with feeling.

I had to make a decision then and there, though. There was no take two. Perhaps I should have asked him to mail me a check for his half. Perhaps he should have offered to do that without any prompting. Perhaps I should have paid only my half of the bill and left him at the wine bar to wash $50 plus tip worth of dishes (or whatever task a restaurant supposedly makes penniless customers do these days). But I didn’t want to leave my lovely local wine bar in the lurch, either. So I smiled and ponied up $100 for drinks and food with a guy who was either forgetful and unemotional or a master manipulator—I’m still not sure.

He walked me to my apartment where we hugged goodbye as he said that the next date would be “on him” and I thought, There’s not going to be another date. And sure enough there wasn’t—no worthwhile follow up from him, no suggestion of another date. And that was just fine with me.


This post originally appeared on The Frisky. Republished with permission.

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  1. X+y=A+B is an equality statement but that doesnt mean x=A or y=B. Yes equal can mean same but it can also mean balanced. In any relationship there is going to be a give and take. Dating is like a dance. Take Salsa for example. We cant both step forward at the same time. The man steps forward while the woman steps backward. I dont believe in gender roles and I dont even care if a man makes less than me. But when it comes to dating I expect him to pay because most likely he asked me out. To me this is him taking that step forward.

    • Mademoiselle

      To play a little devil’s advocate: Do you ask men out as often as men ask you out? Do you treat as many men to dates as the number of men who treat you to dates? If I were to put myself in men’s shoes, I would think their beef is because the argument that “you asked, so you treat” sounds like a roundabout way of putting the onus on men without outright saying “men must pay.” For most women (including me), they aren’t reciprocating the chase, which means men are the askers by default and thus the treaters by obligation. Also, if I were a man, it would frustrate me to hear counterarguments that a relationship is give and take when the discussion is about the first date, which may or may not lead to a relationship. Women tend to withhold the generosity of treating men to dates until they’ve gotten to a point where it seems like it’s going somewhere, but men are expected to be generous upfront every time (while women often tout the notion of bringing enough money to cover her share as an accomplishment/insurance that they don’t really expect to have to rely on more so than a duty). I could see how that makes them feel like they’re playing from behind in that regard, and why they would want to reel in the generosity to their own advantages. Imagine how many first dates they go on before they get a woman who is willing and able to get serious enough with him to offer to 1) split the bill, 2) treat him wholly, and 3) actually do either without expecting him to put up a fight that she would “submit” to because “the thought” counts more than the action.