On the Dilemma of the Damned Beloved
Heinlein, in "Job, a Comedy of Justice", has our pious hero reject Heaven because his beloved pagan wife was not in it. In contrast, C.S.Lewis, in "The Great Divorce", shows a blessed lady send her damned husband back to Hell. I see in this a curious metaphysical moral dilemma; namely, are the saved to care about their loved ones amongst the damned, or not? If yes, then their bliss would be contaminated by grief for the suffering of their damned beloveds; if not, then they attain perfect bliss at the price of rejecting empathy, memory, and ultimately even free will.
The saved with damned loved ones therefore face a Faustian bargain; either love with pain or pleasure without love. This is of course a test of character, pitting virtue against vice. I say that the virtuous choice would be to leave the soulless bliss of false Heaven and enter the soulful turmoil of false Hell, and this for the sake of love; for love is true Heaven.
Hmm… that has fantasy-novel potential...