Kingdom Come: Deliverance

It took me a few hours and failing five or six checks in a row to realize that you can't just rely on the stats shown on the screen; you have to actually pick the option that will work best with the person you're talking to. I lost a lot of reputation before figuring out that it's not always a good idea to pick every single conversation topic offered either.

Failing the speech check involving the unbaptized baby was when it clicked for me and was the most memorable one so-far. In real life it would probably be a bad idea to take the conversation in that direction, considering why Henry was even talking to that person, so it makes sense that it failed.

EDIT: A couple of other memorable ones for me in the early game were while talking to Vostatek's son. Those conversations really made me want to punch him!