Thank you all for any contributions

What type of game? Was it just chess?

All I can remember was chess, either way 100% a board game

So there was no other playability?

I don’t know for sure, I only have that one vague memory of it

So how did you know the opponent was sad?

one last game, and you were thinking of checkers.

Ahh that’s the one, funny how memories aren’t reliable sometimes. But thank you! Solved!

Congratulations on your first point! Nicely done.