Better to have loved and lost?

"It's better to have loved and lost than to never have loved at all", says this friend and smirks at me. Why smirk at me? It's obvious that I have not 'loved and won' or, at least, held on to my 'winnings', considering that I am single (And put a sock in your mouth if you are about to bleat 'ready to mingle'.) But exactly why should he assume that I am of those who have 'never loved at all',