does mom come everyday at the same time? if yes then have him ready at the door with his gear on and plunk him on a chair to wait and when she comes in ...say " jonnys all ready you guys have a nice night." that's the cue to leave. or just have the parent text you when they are 5 mins out. I have a gate at my entrance way so they cant get back to the playroom once they are beyond the gate. I have one little guy who doesn't like to put his coat on for mom and so when she is about to turn on my street she texts me and I get him ready ....so when she comes in he is happy to see her instead of a fight because I have no problem getting his outdoor wear on. most of my kids don't want to leave and instead want to show mom or dad EVERYTHING they played with that day so it is much easier to have that gate so that there is the point of no return.