If you don't try, the only thing you'll achieve is failure.
Think about the last time you wanted to do something in your life but you let yourself or people talk you out of it. No harm no foul, you didn't try therefor you lost nothing. Wrong! You achieved failure when it came to doing something you truly wanted to do.
Next time you wanna reach out to someone or go after something worth while, do it! Don't settle for less, the worst thing that will happen is your right back where you started and a stronger person for it. But your not stuck with the 'what if' factor that breeds regret.