We both had +1 weapons, both were at 18 dex. It most likely had something to do with their light, even though both also had darkvision. Him being 10 feet away had some ray of light in the cave I didnt or something. Its just too finicky. If its going to be like that I wanted to be able to hit a button, like shift does with vision, but its a heat map of where you will get the highest chance to hit.