In my single days, I never looked forward to first dates, even when it was a guy I truly liked. In these post-modern times, we’re supposedly past the point where men need to pay for everything, right? No, we’re not.
Dating in New York City is different than anywhere else, and after a string of dates where the guys didn’t seem to be too into really hanging out and getting to know me, or I would show up and they had already bought themselves a drink and didn’t offer to buy me one, I decided that my new litmus test would consist of whether or not they paid. In every case where I would end up paying for myself, the guy would invariably stop calling, or I would lose interest when he didn’t appear to be pursuing me. I wasn’t beholden to the age-old dictum that the man always pays, but after the realization that a man will not break things off as long as you’re willing to pay your share, because he thinks things are “casual,” I changed my tune.
Every girl does “the reach” on a first date. She reaches into her handbag, seemingly offering to pay for half of her meal, but not really pulling out her wallet because in truth, she wants her date to be the one taking care of her. Everyone can deny it, but it’s a simple truth that if someone really wants to be with you and has asked you out, they should go the full mile and pay for your dinner (without expecting anything in return). So old fashioned, I know. But the real trick is convincing the guy that you are willing to pay, but letting him take care of the bill. The last time it happened to me, I had enjoyed a first date with a nice guy, at a trendy but inexpensive restaurant on the lower east side. It was bingo night, so along with dinner we had built-in entertainment. Careful not order the most expensive food, I ordered a drink that the waitress suggested but definitely noticed that my date stuck with water. I immediately thought he didn’t want to spend the money, or that he was following a 12-step program. Whenever I don’t go with my first instinct, it backfires. We had a great time, but then, the moment of truth: the bill arrived.
I did the reach, well practiced in pseudo-offering to pay the bill, when to my surprise, he took me up on it. I had asked “Do you want me to help pay for this?” and his response was “Are you sure?” Not “no” or “no thanks, let me get this,” but “Are you sure?” To be clear, I was sure: sure that I didn’t want to plunk down a nary penny for this meal. In most cases, it was obvious to me that the guy made more money than I did, but not in this case. I was a bit stunned, but unable to back out, I split the bill with him. He walked me home, we said goodnight, with a promise to see each other again.
I had a sinking feeling that this wouldn’t really end up going anywhere positive, but I wasn’t dating anyone else at the time so when he called a few days later and asked me out for the following weekend to a movie and a meal he would make for me at his place, I figured it would all be sorted out. The day arrived and since I was the one closer to the theatre, I agreed to pick up the tickets. I did so and he didn’t offer to pay me back, which I took full effrontery at. He made me a delicious meal, as he was an excellent cook, but the relationship floundered. He wanted a friend to go out with, but early on we discovered religious differences we had and both of us knew the relationship had no future. It wasn’t until after the relationship ended and I examined my credit card bill that I realized I had spent hundreds of dollars entertaining this little excursion.
As advanced as women are, all are reading this article and laughing at me. Of course he isn’t going to offer to pay, now that I’m so ok with opening my wallet. Never again, I swore, would I offer to pay, and if he had an issue with it, I was sure he would simply not ask me out again. The next date I went on was with a really wonderful guy, whom I really had the hots for. Maybe it was the wine bar we met at, but at the end of the meal, I offered to split the bill. He shook his head immediately and said he wanted to pick up the drinks. Elated, I began naming our children in my mind. However, when he didn’t ask me out for the next seven weeks, I began to feel as though my litmus test wasn’t effective, and so I went on a few dates with a really nice guy who paid for everything but who I wasn’t in like with. And then, I felt cheap, because I knew I was wasting his time and hard-earned money. As fate would have it, the guy I liked called me back and asked me out again, turns out he thought I was just playing hard to get (moi?). Now that we are happily married, I still wonder sometimes if he would have been less impressed with me had I not offered; but I did offer, wanting to impress upon him that I wasn’t a freeloader. In the end, it is an offer that must be made in good faith that it will be turned down.

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