I don't quite get this.
The player decides I wink at the maiden. Who gets to decide whether it's also true that I soften the heart of the maiden with a wink? They're too different descriptions of the one action, so framing things in terms of difficulty doesn't seem to help.
Actually they are not different descriptions of the same action. " I wink at the maiden" is an action. The player has complete control of this action. How an action is reacted to or received is not part of performing that action. Desired effects are just that- desires. Actual outcomes or consequences of actions are often not within the original actor's scope of control. In this case I soften the heart is one possible outcome or consequence of the winking action certainly but there may be others completely unknown to the winking player character. Player agency extends to what they actually say and do. Reactions to those words and actions both from GM controlled NPCs and other player characters are not part of that agency.