I should have
No debí haberme levantado tan temprano.
I shouldn't have gotten up so early.
A veces me pregunto si no debí haberme convertido en abogado.
Sometimes I wonder if I should have become a lawyer.
No debí haberme ido caminando a casa yo solo por la noche.
I shouldn't have walked home alone at night.
No debí haberme quedado despierto toda la noche.
I shouldn’t have stayed up all night.