Now, my doubt is : Should or Would?
Avresti incontrato = you would have met
Avresti dovuto incontrare = you should have met
"Se fossi arrivato mezz'ora fa, avresti incontrato Davide" " If you had come half an hour ago, you would have met David "
" E' una ragazza veramente interessante, avresti dovuto incontrarla " " She is really interesting, you should have met her "