Most of the meanings I see are about Frank Sinatra. The song was not written by Frank Sinatra, it was written by Cole Porter (and, yes, he had his own demons to deal with). However, the song has been sung by many both male and female singers. I think a very important word is "affair". I think this is a torch song sung by someone in an intense affair with a partner who is committed elsewhere (to a family, a career) hence "little fool (singing to him/her self) you never can win". Wake up to the reality that you are never going to get the relationship your heart aches for.
Most of the meanings I see are about Frank Sinatra. The song was not written by Frank Sinatra, it was written by Cole Porter (and, yes, he had his own demons to deal with). However, the song has been sung by many both male and female singers. I think a very important word is "affair". I think this is a torch song sung by someone in an intense affair with a partner who is committed elsewhere (to a family, a career) hence "little fool (singing to him/her self) you never can win". Wake up to the reality that you are never going to get the relationship your heart aches for.