Will & Grace Season 2 Episode 15 Advise and Resent ( Air Date 2000-02-29 ) Genre Comedy category. Overview "When Will is set up on a blind date by his boss, he has internal debates on whether or not to go. Of course, Jack gives Will advice on how to be a good blind date. Meanwhile, Grace continues to struggle with her wimpy boyfriend Josh as Karen doles out some typically un-wanted advice.".