I love your thoughts on the subject, but for me I almost always do this in reverse. I feel like the first few dates we're taking a risk. There's no guarantee we'll hit it off - so I pay for myself for the first few pretty much regardless. I make a point of having the conversation before we meet to save any awkwardness.

"Hey, I'm sure you'd normally offer to pay and I appreciate it, but since we're both taking a risk here, I'd rather we split the first date of you're cool with that." I don't think I've ever gotten push back. And I never have to feel obligated to stay longer than I want to or whatever.

Once we've had time to talk and connect then it's much easier to make a going forward game plan. My serious relationships have always ended up with him paying most of the time. Usually because they make more and they just like to.

But I'm a very giving person by nature, so I don't leave them carrying the whole financial load. I'll surprise us with a couples massage that I bought for us, or get him the stuff he won't buy for himself (for example my last partner was terrible about buying himself new clothes when he needed them, so I'd pick up socks or shirts or whatever when I noticed he needed them).

I think you're right in your general assumption, though. Women will likely think you're broke or going to try to freeload off of her if you don't offer to pay up front.

As always, solid advice from the Chief.