I have this theory about dinner dates. First of all, you can never go wrong when offering to pay for a girl. I mean, I like women's lib just as much as the next girl, but I am also living in a super expensive city and I am not one to look down on free food. Also, if you are the one offering to take me out to dinner, if you pick the restaurant, it seems only appropriate for you to treat. I know this is not a novel idea by any means, but I am hoping some dudes read this and take it to heart. But here's the deal, when you treat a girl, you should do just that. You should not, however, casually say, “Nah, don't worry about it,” but with a slight tilt at the end, which makes me feel like maybe I should worry about it. I am a gentlewoman (thank goodness that is not an oft-used word) and will inevitably counteroffer with my half. I feel like when a guy says, “Don't worry about it” or “It's ok” or “I can get this”, it is a passive aggressive way of saying, “I can pay for this dinner, and I suppose I will pay for it unless you want to chip in for your half which I secretly want you to do but I am also willing to wear the gentleman's hat and handle the bill myself”. And maybe I am wrong, but I don't think so. Exhibit A: Last week you say, “Nah, don't worry about it”, and I respond with, “Are you sure? I can pay for my half,” and then you immediately reply, “Ok, sure, you owe X amount of money.” Confirmation. I knew you didn't really want to pay for me, but you just threw your paltry offer out there because you thought it was what I wanted or expected.
Listen. Be a gentleman, insist on it being your treat without making a big deal about it, hand the waiter your card without a second glance and don't allow for any discomfort or second thoughts. It's not that hard.