“This kind of thing is so awkward and horrible, and from your end, you know it must… Okay, I’m just going to come out and tell you: I’m asking you out. That’s what I’m doing. Please don’t answer yet, because I know you might have a “No” queued up in your head already, but will you please let me say a few things?
I know that being a woman in New York must be hard, because it’s basically disappointing that you try to be nice to men as human beings, and then they respond by just torpedoing to your vagina. And I want you to know that I’m aware that you’re young and beautiful - and I’m not… either of those things. And part of me knows that as soon as my lips stop moving, you’re going to say no. But please think of the fact that it’s low risk what I’m asking.
You just come out with me for a drink, and even if you got up in the middle of the one drink, I wouldn’t hold it against you. Just make a judgement based on nothing horrible would happen if you came out with me. I think you’re so attractive. I’m attracted to you because you’re nice, and you’re a decent person, and those are probably the reasons you want people to be attracted to you, right? Also, you’re horribly cute. I mean, you’re cute as hell.
And I grow on people - women. Some times go by, and you get past the bald head and that I sweat a lot and I’m lumpy… I’ve run out of things to say. Can you just tell me now? Did this work?”