Trial Run:
Prince x Ares
Moon x Xenoko
Wandering Fool x Tim
S.V. x Lilith
Vick x Imagineer x Stella

Odd numbers suck. Anyway, this was, in fact, done at random but interesting choices nonetheless.

Edit: Doubt Ares and Prince can be together for long before violence happens. Hah. Also, think S.V x Lilith might make the most sense.

Dates can be friendly outings as well, doesn't have to necessarily mean romantic just to be clear.