We are masters of the unsaid words, but slaves to those we let slip out.
Crying doesn't mean you're an oversensitive person. It may mean you're childlike but that's ok because Jesus says our hearts should be like a child-trusting, loving, and humble.
Never regret something that once made you smile. If you feel that it is right in your heart then go for it, take the chance and overcome your fears. Taking risks is a big decision but taking those risks is overcoming your fears. If you don't take those big risks then you will always wonder what if...