How do I change my relationship with money from fear to indulgence (every so often)?

I grew up financially poor. We barely scraped by. Everything from food, clothes and consistently having a roof under our head was constantly a problem for our 4 person family (1 mom, 3 siblings). I’m now 33-years-old with a stable job that pays well. After paying my bills, contributing to my 401K, and putting a large amount of my paycheck into savings, I give myself $200 worth of play money every two weeks (so $400) for the month. But I don’t know how to spend it. I’m constantly in saving mode that I’m still justifying every opportunity to spend in an opportunity to save. I want to make a balance and have no idea where to begin because I still feel like I’m nickel-and-diming myself when I no longer need to. Help??