It’s that time folks…I’m gonna talk about money. Specifically when it comes to dating. Actually, the reason I’ve been obsessing about this topic is because it’s the subject of the latest chapter in my book-in-progress. When I’m on a date and the check comes, or even when I’m planning where to meet a date, I panic. What if I pick someplace too expensive? What if I make the wrong impression before we even get through dessert? The whole thing can feel weirdly high-stakes.

I thought the key to monetary peace was offering to split the bill, but my track record with money etiquette and dating is so bad that I don’t even trust this advice. I’ve been on dates where the guy conveniently left his wallet at home. I’ve also been on dates with a man who was a struggling screenwriter living out of his car, so I offered to pay whenever we went out. I never felt like he was taking advantage because he’d do things for me like cook a great dinner and present me with him.

So I am putting the question out there, because I’m writing about my experiences but I have no sage advice about this topic. I’m still confused about the right approach. To me, it seems that money is about power…like, a guy wants to show that he can take care of himself and a girl wants to show that she is independent and self-sufficient by offering to pay for it herself. Sometimes the bill becomes a test even when nobody wants it to be one. Or she just wants the guy to pay for it and be done.

So, why not split the check and avoid potential misunderstandings? Or do you prefer to be taken out, or do the wining and dining yourself? On a first date, I usually offered my credit card, and sometimes that worked fine. Other times, it led to awkwardness or offense. Everyone seems to have a theory, but nobody seems especially relaxed about it. This is for research purposes…