Here’s the thing: Grand gestures – especially financial ones – are very uncomfortable and even just plain crazy to people who aren’t used to it.
Don’t you hate being around the kind of asshole who’s always showing off that he has more money than you? How about the slimy turd who’s always paying the bill but leaves you feeling like he’s running some creepy agenda? Those guys are movie punchlines, villains, or Richard Gere. Don’t start off a relationship looking like a bag of money who’s saving the prostitute.
The gut reaction to this is: “I’ve spent a lifetime being told I should pay for dates and now you’re telling me that women hate men who pay for things? So, basically I’m damned if I do and damned if I don’t?”
No, I’m saying your big, grand gestures might be self-sabotaging. You want to pick up the check? Then try asking the object of your affection if they’re cool with it. Or “Hey, I was thinking of booking something really fancy for our first date. Is that cool with you, or would you rather do something low key?” Remember, there are two of you in this thing. You’ve got to think about what’s not going to make it uncomfortable for her.
If your intention is to impress her with a fancy night out, and she’s on board with that idea, it’s going to be awesome. If your intention is to make her feel like she owes you something in return, you’re not actually a nice guy – you’re just a piece of shit.