No One Knows Who's Supposed to Pay For Dinner Anymore
Question: I met a guy I like and we went on our first date. After dinner I pretended like I was going to try to pay by reaching toward my bag. Most men would intercept at this point and want to pay, but not this guy. He let me pay for half and didn't try to stop me. I was pretty taken aback, because I thought he liked me. Well, he must, because he just asked me on date number two. Should I say yes?
Answer: Poor guys. They just can't catch a break these days. If they insist on paying, they may offend your sense of independence or come across as dominating chauvinists. If they don't insist on paying, they're disinterested, good-for-nothing scoundrels.
I mean, I get it. I too would kind of question whether a man was that interested in dating me if he didn't pay for dinner on the very first date. Even more so if he extended the initial invitation.
I also know that I've often insisted on paying—practically jumping over the table at times. Not because I wasn't attracted to the guy, but because I didn't want to feel obligated if I didn't end up feeling a real connection. So there you have it: proof that I'm hypocrite and that you may be too.
The reality is that there are no hard-and-fast rules anymore when it comes to who pays on dates, not even the long-lived standby "whoever asks pays." The good news? You're not alone in your confusion, and I'm sure that this guy is confused too. So cut him some slack. He's a real person, after all—not just a wallet with a penis attached.
If you're into him and the first date went well (bill paying aside) then yes, of course you should go on a second date. The first step is to figure out whether you have a real spark. Once you do that, you can go hog wild assessing whether he has the level of financial and emotional generosity you're looking for in a partner.
One step at a time.