How about this... At some moment in Bob's proper time, he is able to receive Alice's light cone as they both fall towards the black hole. At a later moment in his own proper time, he sees Alice's light cone red-shifting and disappearing altogether, so he knows that Alice has crossed the event horizon. (It may not make sense to ask exactly "when" she, er, passed over).
Question now is, if Bob continues to fall freely, will there be a third moment in his proper time when Alice's light cone fades back in through the spectrum and becomes visible again? Or would he have to actively chase Alice by accelerating himself towards the BH in order to have a chance of glimpsing her again?