T.V. dating show idea:

The Grim Reaper themselves feels a little lonely at times, so they've been wanting someone to spend time with in the afterlife. The show is about several old/terminally ill/people otherwise about to die soon (the Grim Reaper can tell, of course) dating Grim Reaper to see who's the best match (and of course who's the best kisser of a romantically-inclined skull.) The winner doesn't survive the show but is guaranteed a good afterlife.

I call it Expiration Date.