When I was younger I worked for Wells Fargo converting the old teller machines to new PCs. This required traveling all up and down the west coast visiting new branches every day. It was a long and tiring project and it meant living out of hotels, motels, bed and breakfasts, or whatever else was available in the area. It also meant eating out 100% of the time every freaking meal.
Anyhow one of my team members was an older man. He worked hard, was always pleasant, and hummed while he worked. We got along pretty well and as a result often ate dinner together. While working out of a very small town in Oregon we asked the bank staff for suggestions on getting a nice steak dinner. We were told to go to Idaho. We thought they were joking but it turned out we were practically on the border and there was a steakhouse on the other side.
We walked in wearing ties, sat ourselves down, and were greeted by one of the prettiest girls I had ever seen. She knew we werent locals and we chit chatted a bit about where we from and what we were doing out in the boonies. She checked up on us often and we chit chatted quite a bit which made dinner a lot more enjoyable than it probably was.
When the check came we chatted a bit more and exchanged some parting pleasantries. While walking to the car my coworker asks why I didnt take the opportunity to ask this girl out for drinks or something after work. The thought had crossed my mind but I am a realist... and I knew she was way out of my league. When he heard that he stopped, looked me in the eyes and chuckled. He gestured and said "look around. We are in the middle of nowhere. Shes working as a waitress in a small town. You are wearing a goddamn tie and are here on business. You think she doesnt find you interesting? You think shes got something better going on?
Learn to evaluate the situation before making up your mind."
The last line is what changed me. It didnt necessarily give me any more confidence... but it create a change in me... to not automatically put things out of my reach until I really evaluated the situation.
I didnt go back inside. To be honest I was mostly just tired and the words hadnt really sunk in but you better believe I sat in my hotel room for a few hours thinking about it.
Anyhow the moral of the story is that its not about trying to adopt confidence (dont fake it it has to be natural) its about realizing some things just "appear" out of reach and you wont know til you extend your arm out and try to grab it.