Parametric down-conversion can be used to create pairs of photons that are entangled in energy and time.  Photons entangled in this way are emitted at the same time, but with a coherent superposition of such times, which can violate Bell’s inequality and can be used in quantum key distribution, for example.  We have recently introduced the idea of entangled photon holes, in which a two-photon absorbing medium absorbs pairs of photons from two laser beams at the same time, with a coherent superposition of those times.  Entangled photon holes can also violate Bell’s inequality and may have some advantages in quantum communications.  A recent experimental demonstration of entangled photon holes will also be discussed.