I would tell him that he needed to invest in some Aqua Di Gio just cause the ladies love it, and it would hardly be offensive at all to anyone. For a cooler weather scent I would suggest Gucci Envy. Cause its not to heavy or cloying but nice and sweet and very sexy. This could also fit for the "night out" catagory. As for the formal occasion I might suggest some Rive Gauche by YSL just cause its a cool, classy, masculine scent. Best of luck to ya!