I know how you feel. I didn't really date in high school either.
You do what your heart tells you to do. In the end, there are realists who follow their head at all times, there are romantics that follow their heart with no remorse, and there are those of us who are so strong minded and romantic at the same time...and it's a constant struggle. I'm that way; but, in the end, everything always falls into place.
You have to learn the game of life, make mistakes, and suffer before you can know when it's worth it, and when it's not.