If a girl said, "I'm out of your league, but I'll let you go on a few dates with me." What would you say?

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“Well threaten me with a good time! How about Tuesday at 8? I’ll send an Uber.”

First dates typically cost me around $2–400. This is because I typically do what’s called “sugar daddy dating.” Not only do I have the cost of the date to contend with, but also a substantial cash gift.

I started warming up to the idea when lack of resources (on her part) started becoming a real sticking point to getting dates. I’d hit it off with a lady only to have efforts to get to know her bogged down by the fact that she has to make a living. I gave up on dating for a few years until I found out there was this thing called sugar dating.

And the few times I could get someone to spend some time with me, I would leave the first date with more questions than answers. Trying to actually sit down with someone over dinner and drinks later so we can assess compatibility and I might as well be asking these poor women to go hungry for a month.

And then the few times we’d actually do get to get together there’s no actual connection taking place. I’m a little tone-deaf sometimes on when to transition from chit-chat to flirting.

So all this led up to the idea of just throwing money at the problem. Line everything up, knock down all the obstacles, and actually connect so that I can get a feel for who you are and whether I want to spend more time with you. But you can’t just offer $250 to a random girl you meet to incentivize her to actually show up. I dunno, maybe nowadays you can. I should think about that more.

Sugar dating makes everything rational. If something didn’t work for me, I can tweak my dating system and come up with a different approach that solves the problem.

Back to our little princess. The point of the first date is to connect. I’m going to deploy every last bit of my interpersonal know-how in order to make that $300 money well-spent. I’ll tell you all about how I was as a kid, what sort of upbringing I had, what I spent my whole twenties doing and how it finally came about that I can spend that kind of money on dating.

And then I’m going to ask you about yourself. And that’s when I shut up and listen. The sorts of things I told you are going to lay the groundwork for what you tell me. I’ll treat them like they are really really important to you, and ask you followup questions. I may be the first person in your entire life who has actually done this for you. I’m not going to spin everything you tell me around so that I can talk about myself more. I have Quora for that. I wanna hear what you have to say.

The sort of ego that would lead a girl to say something like that cannot possibly survive in the context of authentic relating. You are sitting down with someone who devoted a great deal of time and expense and trial and error to hone a date technique that ensures that we are going to actually connect, gosh-darnit.

Because I spent my entire twenties in this awkward hell of never having it happen, except maybe once or twice and then it went nowhere.

You think you’re out of my league? Hah! Bring it, we’ll see whose still feeling that way later. Very probably, you’re going to end one of the best nights of your life with a pocket full of my twenties, why is it so hard to get hundreds, and a hope you’ve finally met, if not the man of your dreams, but at least a guy who has it where it counts.

And then it’ll suck when I have to tell you I’m not interested in another date. Because while we had a connection, I couldn’t really see myself with you. I can connect with anyone, but I can’t actually build a relationship with just anyone.