If you consider yourself a shy or awkward person, the encounters you've had were probably far less awkward than you thought they were. You can build a little self confidence and dispel some shyness by re-evaluating your social encounters in a positive light.
Brett and Kate McKay at The Art of Manliness explain that shy people have a tendency to draw negative conclusions about themselves when they look back at past social interactions:
This is also known as "me/always/everything" thinking. A shy person with a me/always/everything mindset automatically believes that when a social encounter goes less than ideally, he is the one who caused the problem (me), that he invariably makes social encounters awkward (always), and that his social faux pas undermine all aspects of his life (everything). If the shy person were to actually sit down and think things through, he'd likely discover that oftentimes it's not his fault when a social encounter goes awkwardly...
Me/always/everything thinking -- a concept developed by psychologist Martin Seligman -- is a trap that many shy folks fall into. There's nothing wrong with being shy, but you shouldn't only look back at the awkward aspects of your social encounters. Stop thinking that everything is your fault! If you take some time to really look back, you'll probably see plenty of interactions that went really well. Remember, being shy is a breakable habit, and people pay much less attention to you and your actions than you think they do.
Help for the Shy Guy - Step 2 [The Art of Manliness]