Well then he is definitely looking for a partner caregiver IMO. Is your friend financially stable? Is she a nurse or a clinical professional in the healthcare community? Does she do a lot in a friendship or relationship? Does she go overboard with trying to win people over, or being extra nice? I keep saying women need to be honest about men, marriage, and motives. Men pick and go after women according to their level of what they can accommodate. This man could have been married a long time ago, and now he wants to settle down with a BW? I suggest premarital counseling. If her gut is telling her something is off, she and nobody else should be dismissive of it.