Possible Results:
hubiera dolido
Past perfect subjunctive yo conjugation of doler.
hubiera dolido
Past perfect subjunctive él/ella/usted conjugation of doler.

doler

Probablemente me hubiera dolido más de haber perdido la de mi mejor amigo.
Probably would have hurt even more if I lost my best friend's girl.
Más, me hubiera dolido.
Any more, it would've hurt.
Eso me hubiera dolido.
That would have really hurt.
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early