Since I was a kid, I’ve always questioned the reasons people did things a certain way. When my mom told me to hold my fork properly, I asked her why? Isn’t the point of holding a fork to help the food get to my mouth? Why should it matter how I hold it? When I was instructed to say, “Nice to meet you,” upon meeting someone, I asked her why I still had to say that even if I didn’t think it was nice to meet the person. Wouldn’t it be more honest if I just shook their hand and didn’t say anything? And it still kind of bugs me when relative strangers ask me, “How are you?” I don’t believe they really care, and would prefer not to be obligated to say anything less than the truth, not that I’d want to share the truth either. I just think it would be more polite not to ask how I am in the first place.

Now in adulthood, I’ve adopted most of society’s manners to blend in well enough. Arguing over the efficiency of silverware holding wasn’t worth the stress, so I adapted, and I find this to be the case with most other courtesies of social decorum. If it doesn’t hurt or go against my convictions, why not go with the flow and appease the masses? But when it comes to dating, the rules of propriety aren’t quite so clear, and I find myself asking, “Why?” with even vaguer answers than the ones given me in my childhood.

I don’t know how to date. The money thing has been plaguing my mind recently, so that’s what I’m going to write about today. If I open my wallet when it comes time to pay for dinner, I’m told not to be silly and put it away. If I don’t, I sit there feeling horribly awkward for not offering. What to do, what to do?

Most people seem to agree that the man should take the bill on the first date. If he’s a man of quality, he’ll insist upon it. (This is what I’m told.) Yet I’ve heard complaints from guys saying, “She could’ve offered.” They weren’t talking about me, but they could have been. Maybe I’m just naive, because I’m not trying to be cheap or take advantage of anyone, but what’s the point of offering or reaching into my purse when we both know he’s going to buy dinner? Doesn’t it seem like a false gesture? Does he want to hear me fake protest? Does it show him that I’m not a spoiled girl with assumptions when I say, “No really, let me pay”? Is it supposed to show me he’s a true gentleman when he brushes my money aside and says, “Nonsense”? Can’t we just skip over the pretense, and I’ll smile without reaching for my wallet and say a sincere thank you when he hands the waiter the check? Or is that ill-mannered?

I wonder what guys think about all this. My hunch would be that most of them wouldn’t let a girl pay, but they’d be charmed if she offered. Now, why is that? Because my hunch is also that most girls aren’t really coming from a place of pure sincerity when they do this; they’re testing him, consciously or unconsciously. If he says, “No, no, put that away,” when she hands him her credit card, she smiles inside. He passed. But if he were to say, “Your meal cost $15 and your drink was $10, so… I’ll have the waitress put $25 on your card,” she’d probably be shocked at first, then turned off. He failed.

When the man picks up the tab, it often signifies that it’s a date, if it wasn’t completely clear beforehand. (Exception: when the man is a friend I’ve known for a long time and all air is clear that we aren’t anything more than friends.) Here’s a scenario I found myself in where the to-pay-or-let-him-pay thing became a clarifying issue…

I found myself on a date that I didn’t know was a date when the check came. An old friend I hadn’t seen in a while wanted to get together, and since I was working during the day, evenings were all I had available and I suggested that we catch up over dinner. When I reached for my wallet, he said, “No, I’ve got it.” I said, “Are you sure?” and he replied, “Well… aren’t I supposed to pay? Isn’t that what the guy does?” I immediately realized that he thought it was our first date. It was very awkward, and I ended up telling the waitress to please split the bill. Perhaps he felt I led him on by suggesting dinner—if I didn’t want to confuse him into thinking it was a date, should I have said coffee or lunch? I honestly didn’t have time that week and he was going out of town before the weekend. We’d never dated before, so it seemed rather practical and innocent for us to just have dinner together. I think my refusal to let him pay told him without words that we were not on a date. He also surely saw the flash of dreadful realization in my eyes.

Here’s another thing… If I don’t want to kiss a guy, I don’t let him buy me dinner, because then I’d feel obligated. It’s the reason why—with few exceptions—I don’t travel out of town with a guy who’s not my boyfriend, because then I’d feel like I had to sleep with him. Even if he doesn’t make any overt moves, I still feel his expectations, and at the very least his hopes, no matter what he’s said to put me at ease. Sometimes when a guy hasn’t been clear that we’re on a date—an inexplicit “we should grab food sometime” vague sort of thing—and he insists on paying, I feel like he’s slyly trying to purchase a goodnight kiss. Perhaps this is my own overly suspicious hang-up, and he’s really just being nice. It would certainly be more rare than common. But if I didn’t know it was a date, and let him pay, and he went in for the kiss when he dropped me off, my reaction even just a year ago would have been one of shock and horror. I feel like I’m five years old again, learning that we’re not supposed to take people at their word. “Nice to meet you” doesn’t always mean “nice to meet you”; a friend buying you dinner doesn’t always mean a friend is buying you dinner.

So, in effort to keep up with what’s socially acceptable and expectable, I now expect men to pay for our first few dates. Yes, expect, and I’m very uncomfortable with it. I don’t like it, but it just seems to be code for “this is a real date and I am really into you”. (In an ideal world, they would just tell me that beforehand.) I love to treat the people I care about to meals and events, and if we advanced into a relationship, I’d be offended if he never let me buy him anything. I get as much pleasure out of giving as I do receiving, but I also wouldn’t want a guy I liked to be turned off by my insisting to pay so we keep things square and even.

But I’m still left wondering… Should I at least offer to pay?

What are your thoughts and experiences with this?