Seeing as you really care about him I have no doubt he will get more comfortable with it. >I spent last night basically telling him that it’s ok if he stutters etc. This is good of you but don't overdo it. You told him how you feel about it. Repeating it will just remind him of it, make him more aware, which is not something you wanna do (obviously). Also there are ways to reduce stutter. The oldest method is reading in front of someone/mirror. Also some people wrote about it, i remember reading Steve Harvey talking about having a big stutter and look at him hosting game shows now!