The biggest thing that helped me to stop being shy was Sam. My boyfriend is the most outgoing and gregarious person I have ever met. He thrives on social gatherings- he's basically my polar opposite. Before I met him my bestfriend knew how shy I was, so she helped me out. She would answer questions for me in public and she had a way of making people think I was social when she was the one doing all the talking. I loved her for it, and I still do, but Sam does the opposite and it was such a blessing. He would take me to parties and then leave me alone with a group of people I didn't know, or he would force me to join in for a game of frisbee even if I said I didn't want to. He never answered questions, made decisions, or asked for help in stores on my behalf, so I was forced to do these things myself.
As time's gone on, I've continued to do things that make me uncomfortable. I go to fairs by myself, I sign up for classes that sound fun even when no one will do it with me, and I talk to strangers. I decided not to be shy, and I am so much happier without that burden weighing me down. I still get nervous trying new things and meeting new people, but I've taught myself to push through it and it's led me to amazing opportunities and wonderful friendships that the old me never would have had, not in a million years.