They need to communicate and finally set boundaries.

High school drop out have low self esteem the other thing is why not go get his GED so he can keep up with how things are instead of being jealous and using sex for everything also MR exam boy there don't give him too much reassurance

Exactly, he should continue his education and get decent job, did he have no savings from his time of being a manager/kept guy? If that's the case he needs to be better at managing his finances and career and not feel so insecure for being dependent