...so I tried bleeding the rad again and don't think I was successful. I was turning it and turning and the bolt came out pretty far, that can't fall out can it?
Yes, the bleeder valve stem will come out if turned too far. Without a properly operating shut-off valve (the handle is broken off on yours and the valve stem may also be broken giving the illusion of ON/OFF when turned with pliers but not actually opening all the way to let hot waster into the radiator) you may have a heart breaking experience...
Shut-off valve with handle shown below and parts explosion of your type bleeder valve-