Online Dating?

So,
in an effort to break the 3 year slump, I signed up for a month @ a single parents dating site. I figure I might have more luck @ a site that caters to single parents, then again, I might not. BUT I told my sister that she got to choose my next "boyfriend", because I pick losers. Or they pick me. There was the fiance that was in the closet, until about 8 months before our wedding; the guy who mowed mud (not the brightest bulb); the guy who had the pregnant ex-wife AND was dating 4 other women @ the same time (that was the last one, boy did he ever snow me); the narcissist... those are the ones that I went out with more than a month. There were several that I recognized as losers right off the bat. Honestly, the best relationship I've had was with my sons father, but that was short term, due to his living in another country and all. Then once he found out, he disappeared.
ANYWAY back to my original thought process here. Since my sister is supposed to pick my next "boyfriend", how is that going to work on an online dating site? Am I supposed to tell someone "Sorry, you have to pass the sister test first"?
Why does it have to be so hard to meet a nice decent man? sigh...

"I'm not one of those guys"

Seriously? O.K. so I was reading "He's just not that into you", and I just began it, but the first chapter or so talks about how guys DO NOT like it when women ask them out. Apparently they like the thrill of the chase. They need to feel like they were in control of their destiny.
O.K., fine, good, I can handle that. Rule 1. Let them ask you out.
However I have a tip for you boys, guys, men, whatever you are calling yourselves these days.
Never tell a woman "I am not one of those guys" , because that tells us that you are.
If we tell you that we are not ready to let you know our phone number, our address, our place of employment, or any number of things it is because we do not know you well enough yet.
"What do you think I am going to do? Stalk you?" Well we might, or we might be concerned for our kids, if we are single moms, or hey it just is not that smart to be telling someone all of our private information right up front. Don't take it personally, we do it to all the boys, guys, men, whatever....

What do you think?

I know that not many people read this blog, and that is alright, but for those of you who do tell me what you think.
Times have changed so much in the last 15-20 years, and gender roles are not what they used to be. Is it alright for a woman to ask a man out? I mean I am pushing 40, I have never been married, and I am more than ready to break the 3 years since my last date record. So is it alright, or accepted to ask a man out?
Well I did. Sorta. I sent him an email on MySpace. He is someone I used to work with, and still works with my sister. He is a really sweet guy, and we have a few things in common. My sister kept telling me that he liked me, so I figured I would ask him out and see what happened. Well... I'm thinking that maybe I should of asked my question prior to taking the plunge, cuz I got no reply.
Also, in the age of "cougars" how many years difference is too much? An older woman and younger man situation, has always bothered me. For me it was 2 years younger was my limit. Now it seems more acceptable, so how many years is too much? 5, 8, 10?