I can only speak for myself, but after having a long period of barely being able to get past a sentence, when I have something to say, I say it. I always want to make sure my point is understood and my voice is heard. There’s a good chance this guy will put in the extra effort addressing and communicating anything that needs it. In terms of asking him to repeat himself, it’s nothing to feel bad about, it just is what it is. What often times happens when you have relationships with people who “talk funny” is you get used to how they speak after a while. This isn’t exclusive to stuttering. My wife has a thick accent and her English is far from fluent, which hasn’t changed much since we met. It’s hard to explain but I just kind of understand her code now, what would have been vague years ago now makes sense just because I’m used to how she talks after being around her for so long. As long as you guys make sure you’re always understood, I can’t imagine communication will be compromised between you 2. Having a stutter can ruin your life if you let it. This guys really sounds like he has his life together and the fact that he’s accomplished that, despite having something so debilitating, says a lot about him. Sounds like you found yourself a catch, give it a try.