yes, and if it was criminal maybe you should ask someone else (legal) for advise, too

You already know the answer if you couldn't trust him on the street.

Yes, there is minimal supervision, the doors do not lock and you are not confined to the indoors, so the possibility exists

Lucky guy, if true

ask him

Yes, I have 6. Here is my assessment: There are some factors on the outside that have to work in your favor for an inmate's relationship with their kids to be "normal". If the spouse with custody of the kids supports the inmate emotionally and familiarly, then the kids see the example set that this will all work out. BUT, if the spouse is filling the kid's head with negative stuff about their significant other, then the setting changes 180

Don't even try to entertain him 24/7, it is impossible. Right now, he is testing you to see how far he can push you. What will you do for him? You have to set the rules and the boundaries. You need to make sure you are budgeting for YOUR life first. Inmates have a way to make the loved ones outside feel pity for them. Just remember that inmates have all day and night to think. Inmates are very creative

20 years! WOW, you are the "ride or die" girl. Think about the world 20 years ago, cell phones had no texting. The internet had no social media. Technology will shock him. He is going to take some time before things can go back to a normal relationship like before.

There are only a few places an inmate can spend money on, but be mindful that everything is super-expensive. starting with the phone calls... In my first month away, my wife spent over $6000, which translates into a lot more than $500/wk. Commissary is another area where an inmate can spend $200/wk easily if it is in their account. If there are daily fees from the jail, medical charges or fines, they could be debited from the inmate's account, too.

Send him a sexy picture of yourself (no private parts showing) and tell him how you feel