Emily

When teenage Justin’s sexual explorations are sabotaged by Emily – an old flame and the ghost who haunts him–he must reconsider his previous promise of joining her in the afterlife.

This gem has so much going for it.  The young man isn't exactly grieving for the loss of a girlfriend, at least not in the way film or media commonly portray grief.  But he is, and in an artistic vein we see how he can best work through grief.