I'm wondering how much does confidence matter in these situoations? If you had success with a man you (secretly) looked up to, was down to sheer confidence, or was it flattery admiration that worked?
A bit of a backstory. I've contacted this man on a dating site, I REALLY like everything he said, the photos (no Greek God but really appeals to me), he also (!) included a photo which was published in eligible bachelor section of a glossy albeit years ago 
, though he doesn't look as good now - he made a funny comment about that, and if you are wondering, it wasn't that that made me interested, I noticed the fact later in his long intro. He is obviously talented, he is a publushed poet, he states that he is comfortable financially and I just love his sense of humour AND his voice recording. He sounds kind and not dull like so many online guys. He also does sound very confident behind the humour. I was like that as normally I find very very few men online interesting and worth contacting and none so far compared for me. I know, I know, he may be an arsehole with issues in RL, as he never got married and he is approaching 50. But I want to meet him at least.
He hasn't replied to me first time round, so I wrote to him again 
after listening to his voice once more, thinking that it was unusual for him not even to ask questions, even though I haven't ticked some of his 'potential partner' boxes, but normally men like my photos (nothing revealing or overtly sexy) and at least attempt some dialogue. I felt I wanted him even more as he is a challenge. He said he'd prefer a woman with English as home language while I'm foreign but spent all my grown up life here, he also said she needs to be in or near London when I'm not, though I do visit quite often. He also wants someone with a good stable social circle which really I don't have as i didn't study here and just have a few friends, not a 'network'. When i wrote to him i explained that I know I'm not 'perfect' and then asked him, the second time, whether he is sure he doesn't want to meet. He now replied with an auto reply that he will write to me when he subscribes. It's very easy to sunscribe so you can send mesages, if anything you can do so for a week for under 10 pounds, it's been two weeks since mu last message and a day or so since his reply. Obviously he is not that keen.
Do you think it's worth pursuaing or eve nmeeting if he does reply? He is a bit on a posh side with his speech and looks, I just worry that English guys like this are really snobsat heart and even if attracted to a woman, just wouldn't see her seriously as LTR partner material? He is not the only example of a man I'm attarcted to but don't 'push it' out of this lack of confidence/cynicism. I always hide the lack of confidence by playing cool if met with lujkewarm response, or with just physical interest, but deep down I want to be braver and try a pushy approach. Did this ever work for you, when yo knew that socially and possibly financially he is of higher status?
Is it worth it or not, as even if you gain his interest you may have to prove yourself for a long time to him and his friends etc.? I do admire Kate for being so thick skinned what with the sniggering from William's friends, before he proposed. Yes, it's nothing like as this 'high up' in my case but on a smaller scale still applies.
If it did work for you, do you think it's because he just liked you and you didn't actually put any effort i.e. luck of the draw, or did the efforts you made paid off, and any advice in this case? Is it justa case of being brazen and forgetting about all the issues?