With respect to him not leaving, could you put money down for the first month's rent for an apartment somewhere? That should give him enough time to figure out how to support himself. That might be easier than just giving him money (which could potentially set you up for him to claim spousal support, on the grounds that you have already acknowledged a financial responsibility towards him by giving him money). One bit of legal information I retain is "never give cash to a soon-to-be-ex unless you want to keep giving them money indefinitely ...".