I think he should just get laid already. His idea of doing it with someone who cares is fraught, as there is a good chance he will get dumped and it will be crushing because of his circumstances, and because it wont mean as much to his first partner there will be a power imbalance in the relationship. He may also be so smitten that he ends up marrying the first one even if she isn't the right choice. Once in this marriage he will soon be regretting not having other experiences.