The OP reminds me of one of my worst date experiences. One of those that are so horrible at the time, but now you love that it happened because it is such a fun story to tell.
I had just starting dating this guy who at 33 had just gone back to school for his masters. Full-time student, no job, I understood our dates would be doing things you can do for free, no problem.
Well one day he says he would like to take me out for a nice dinner. I think that is a nice gesture, figure he plans to use some of his birthday money he recently received, but just in case, I have money and am prepared to pay. I just feel awkward asking ahead of time.
We get to the nice restaurant, he proceeds to get the most expensive bottle of wine, and the most expensive appetizer, soup, salad, steak and lobster, and dessert, and after dinner drinks. All I have ordered is a salad, and appetizer for an entre. I know the bill will be high, and even if he planned on spending all his birthday money on it, I will insist on splitting it with him. But I am feeling quite fond of him, thinking he was willing to spend his money on me.
I was wrong, the bill comes, and he looks at me. OK, I will pay it. No big deal. I reach in my purse, and he starts to freak out.
“People can see you getting money!” He quietly “yells” at me. “What?” “Don’t let anyone see you are paying the bill. Makes me look bad, hand the money to me under the table, so they can see ME pay the bill”.
I really think he must be joking. He is not. When I just sit there, confused, he starts to really get angry, I am scared now. I don’t know what the bill is, I ask. He is mad I just don’t hand over all my money I guess. He tells me. I give him the amount for the check, and 25% tip. The service wasn’t really very good, a cute young girl, but not very good, but I can round it out to 25% easily, and that is what I give him. He takes the money, looks at it, and says he needs more, 25% tip is not enough, the waitress will think he is cheap.
I really am scared now, so I give him more money. He kind of snarls, but takes it. I would like to say that I left the restaurant, took a cab home, but I didn’t. Low self-esteem is a terrible thing. I continued dating him for almost 2 years. And learned to be very discreet when handing him the money under the table whenever he said he would like to take me out for a nice dinner.
After I finally was able to get away from this guy, and started dating my now husband, on our third date, I told him I was going to take him out. He said I didn’t need to, I insisted, he relented. When the bill came, he still wanted to pay it, I said I would, but out of habit, I asked if he wanted me to hand him the money under the table so he could be seen paying the bill. That totally freaked him out. “Are crazy? What could be better than being seen having a beautiful woman dining with you? A beautiful woman who picks up the tab!” Just then the waiter came over. “Can you believe my luck? I get the honor of dining with this incrediable woman, and now she wants to pick up the tab, life does not get better than this, does it?” “No sir, it doesn’t.” And the waiter winked at me. And to top it off, when I gave the waiter my Visa card, he said sorry, they didn’t take credit cards, only cash. I didn’t know any restaurants were that way and I had no cash. So my future husband had to pay anyway. And that is his favorite restaurant dating story.