you were supposed to be; you must have been
Dovevi essere con Tom ieri pomeriggio.
You were supposed to be with Tom yesterday afternoon.
Non dovevi essere in custodia alla polizia?
Weren’t you supposed to be in police custody?
— The Man from Nowhere (2010)
You should have been prepared.
You had to be prepared.
Non dovevi essere alla festa di Elton John.
You weren't supposed to be at Elton John's party.
— Love Actually - L'amore davvero (2003)
Non dovevi essere in Salvador?
Weren't you supposed to be in El Salvador?
— Tutto su mia madre (1999)
Quando l'hai scritto, dovevi essere molto innamorato.
When you wrote it, you must have been very much in love.
— La grande bellezza (2013)
Tu dovevi essere con Tom ieri pomeriggio.
You were supposed to be with Tom yesterday afternoon.