Flattering or insulting?

So, the question I posed today was whether a somewhat-less-than-attractive guy asking a really 'put-together' woman out is flattering to her, or would she take it as an insult that he would even think he had a chance. By 'put-together', I mean the whole package...not just physical attractiveness, but also mental acuity, personality, all of it. Now this may seem a silly question at face-value...why wouldn't she be flattered? Even if she has no interest at all, she should feel good about herself that someone would find her attractive, right?

Not necessarily, at least in my warped head. There's a huge difference in my mind between letting her know that you think she's attractive, and moving to that next step and actually asking her out. By asking someone out, I'm saying that I have some to offer that she doesn't already have...that I'm going to add some value to her life. I know most guys don't see it that way, unless they're defining 'value' as their cock. My intention when I ask someone out isn't to get laid, though...maybe it was in high school, but we're adults now. It's all about relationships, not getting off.

By asking her out, I'm saying I'm bringing something to the table. Maybe it's just a self-esteem issue with me, but when I see certain women, I don't really feel I have much to offer. And just like if someone less fortunate than I were to offer to give me money, while that would certainly be nice, I'd have to wonder why they thought I would need such a thing. Hopefully it's obvious that I have enough money to get by, and I'd be a little flustered as to why they would offer. I think that my hypothetical 'put-together' woman would look at me and wonder the same thing...why would he offer? He's not really bringing much to the table, does he think he's got something I need? What image am I putting out?

Or maybe I just need a visit from Stuart Smalley. I know, at a rational level, that I am bringing SOMETHING to the table. I'm not a troll, I have a job, I have a pretty good sense of humor, etc. But it's not enough in my mind, and I'd rather not put her in that situation where she has to wonder. I sit back, talk, and hopefully over the course of time I can prove my value. Or someone else will ask her out, and I'll wonder what might have been. Regardless, my method has allowed me to over-achieve time and again, and it's a hard thing to change. But change is not a dirty word...just a difficult thing to accomplish.