It's tricky but I got it on my second try. Two things: 1. for some reason I thought it was asking me to alternate the keys which is not what you do, you tap left or right depending on the icon. It's probably just a me thing, but once I realized that it got easier. 2. With the bartender, you want to win as fast as humanly possible or else you'll get tired out. I alternated fingers when I clicked, but if you dont win in the first like 3 seconds you'll lose. Hope this helps.The arm wrestling game with Bartender is not humanly possible on a keyboard and mouse... not even a person with parkinsons can fuckin click the right and left arrows that quickly
Edit: i have the ring that is mentioned and have the arm wrestling bonus with Intimidation also maxed out, im very frustrated at this point
Edit 2: nvm i just said fuck it and lost the match instead of rewinding, he is supposed to lose fml i wasted around an hour on this