Should i be bold or let it go?

Ok so im 17 and im stuck on a boy.lol We both have history together. We started talking about a year ago and we were very serious. He was my first of everything. My first kiss, and the first person i had sex with. The only person. Anyways after a while we started talking, we started to get distant. We ended up not talking anymore but he would always hit me up. I lost my virginity to him waaay after we stopped talking. But he would just text me out of the blue he still does till this day. Hes told me his feelings about us snd ive done the same. But i never teslly knew if i had a chance. Ive never texted him first. Its always him. And im just scared to text him cause i feel like he wouldnt want to talk to me. I really like this guy and hes the only one that i have feelings for. Should i just go for it and if he doesnt seem interested just let it go?