Another of my players is a level 1 former mercenary from a company who occasionally turned to being brigands when times were lean.
About 50 feet away, they hailed him and said they they needed him to come with them to answer some allegations. As they closed within 30ft of him, he decided to flee on his horse.
First off I think this situation is murky and impenetrable. I don't think we have enough information - I don't think we as a forum can ever have enough information - to work out what actually happened during this exchange. So what follows are, really, questions and musings and I hope are taken in that spirit.
A brigand is approached by the town guard to 'answer some allegations'. Why wouldn't he run? Why should he believe that running and escaping isn't going to be cool and cinematic, Robin Hood style, vaulting the stable door on his horse, being chased around town, rolling under the gate as the portcullis comes crashing down. Giving the other characters a chance to get involved in this scene and unite against this awful smear.
Maybe he crosses paths with the woman as he's fleeing and she sees the terrible injustice she is unleashing. Who knows how that might have played out?
What was stopping you taking these options?
I feel that by giving the players "hints" like my friend wants, I undermine the nature of the game.
RPGS are a conversation. Poor communication is, imo, synonymous with poor play. It cuts two ways, but when GMing I feel a responsibility to communicate clearly and effectively and in the spirit of fun and co-operative enjoyment.
I think it's difficult to claim 'hints undermine the game', especially having told your player the following, essentially pre-playing his escape plan as a failure...
I informed him that they might be able to intercept him before he could mount his horse and ride out of the stable, that the main gate might be closed, and that even if he did make it out, it would mean he may as well roll a new character.
Why did you inform him of that? Why is a false and horrible accusation 'a challenge' but a daring escape from injustice not a challenge? Without a communication of ideas how does your player know he's starring in To Kill a Mockingbird instead of The Fugitive?
Further, the town would see his flight as an admission of guilt...
Was this a threat to the player or a challenge for the PC?
Do you believe this situation arose because of the specifics of this scene or was it a flashpoint which had been building due to an ongoing mismatch of ideas or styles or personalities?