I still don't consider my photographs to be comparable to those who I seek encouragement for but I continue to aim for images that are worthy to those who have given me the opportunity to pause a few moments with.
Photography is a lot about being brave and really trusting you eye. Every person is interesting and unique and a lot of times all you have to do other than having calculated the settings for your camera right is to wait for the moment when that person's personality erupts on the spot mid conversation.
The wording of the question I feel has made a difference or at least in my mind it has. When I come across an individual who lend themselves for a great suitable snap shot based on the location, lighting and overall presence, I ask not for a "photo" of them but rather a "portrait". I realize they're both synonyms but the phrasing has mean the difference between getting a yes or no in my case.
I was recently found myself in Fort Greene, Brooklyn at Red Lantern Bicycles. The business is unique in that the front portion of the business caters to a quaint coffee shop while the back caters to the labor of fixing your bikes which is ran by Brian. Which ever area you chose to visit based on your desire, you're bound to encounter a sincerely friendly staff on both ends of the business.