any chance you would design it to allow a second non sexual interaction via some sort of upgrade? It just seems odd that building upgrades can allow you to have group sex numerous times but a second date is just not happening.

I agree,  esp since most dates don't result in sex *AND* date can be used for training  *AND*/OR improving LOYALTY.      (Loyalty factors a *LOT* on Obedience, in fact at 100% Loyalty,  Obed never drops! )

Since we're talking about Dates  (hope Strive4 reads this)  should be able to have the "date"  at any town,  shouldn't have 2 have both come back home everyday  (many lost hours/Obedience) just 4 date & then go back out again.    ("sex" part could be done later---or skipped.   Since Dates affect Obedience, stats, Authority & Loyalty,  most important to not miss those while sex can be skipped)