We refine previous investigations on de Sitter space and extremal surfaces anchored at the future boundary I + . Since such surfaces do not return, they require extra data or boundary conditions in the past (interior). In entirely Lorentzian de Sitter spacetime, this leads to future-past timelike surfaces stretching between I ± . Apart from an overall −i factor (relative to spacelike surfaces in AdS) their areas are real and positive. With a no-boundary type boundary condition, the top half of these timelike surfaces joins with a spacelike part on the hemisphere giving a complex-valued area.Motivated by these, we describe two aspects of "time-entanglement" in simple toy models in quantum mechanics. One is based on a future-past thermofield double type state entangling timelike separated states, which leads to entirely positive structures.Another is based on the time evolution operator and reduced transition amplitudes, which leads to complex-valued entropy.