Love, Career, and Money: I was born Feb 7, 1976 and the guy October 27, 1977.

We broke up 16 years ago and haven't spoken to each other since then. We just reconnected a few days ago, so I am wondering if I should let him stay where I left him 16 years ago or give it another try. My other issue is whether I should go back to school this year and do what I love to do and will I be successful at it.