Crazy idea.
That night if the party the player has to roll charisma to flirt and do the one night stand.
Lmao.
Ha ha, I actually like this, as long as it's not a "hard fail" (no pun intended), depending on your standing. Witcher 3 had some funny moments (not die roll driven obviously), but what if you had a GOOD standing with your beau of choice but failed the charisma check, I would hate it if they went all sourpuss, but maybe something funny happened. Referencing the Witcher again, what if Shadowheart needs longer to get in the mood because of your die roll and falls asleep or drinks too much and vomits. (See Shani in W3 for details). It's funny or quirky vs Hard Win / Hard Fail. The character who technically likes you could be sheepish or want to ignore it the next day without the "your die roll just got you relegated to the bench until enough in game time has passed to try again".
Obviously if standing not on sure footing, then the Charisma roll takes on more meaning, i.e. going for broke and with the harder consequences that may or may not bring, depending on character. Or perhaps a character is straight, but you use your wily charms to come round to your way of thinking!
