Hi Maddie,
Jade will begin staying out all night any time now and the worry for her will begin. This will go on until Oct when the weather starts to cool down. Thankfully through the Winter months and into Spring, she sleeps in the house - a relief. Even when she's outside, she is always here, I can always find her, so I assumed she didn't roam at night. I was wrong. One of my neighbors works the night shift and a few yrs ago, saw her walking all 'lady like' (his words) near the curb on the street around the corner from me one 3am morning. I felt so upset hearing that.
Our kitty before Jade did what your boy does. Stayed out all day and all night. I used to be obsessed with finding her (I never could) and darn near worried myself to death over it. So I understand how you feel completely! I have learned not to worry so much about Jade though. There's simply nothing I can do about it, but I am always relieved to see her in the morning. :)
Tweety did when I first had her, then I started shutting her in in the evening worried about coyotes, she adjusted okay ..doesnt really want to be out at night here so many dogs with barking..I could never sleep when she did stay out