Good for you for being thoughtful and for taking the initiative in learning how you can be supportive towards the guy you're dating. To answer your questions: I probably wouldn't tell him that his stutter is cute. There's a good chance he'll feel a bit objectified about this, and for most people in his position, stuttering may be a big part of his life - it can go deep and shape a lot of their personality and their life. But with that said, if you do decide to 'compliment' him in this way, it could lead to an interesting conversation. As for generally bringing it up, I think that's fine, particularly if you ask it in a way where you'd like to learn more about it, and are curious about it because you haven't ever dated someone who stutters, or something along those lines. If he is okay talking about it, you're in the clear. If he's not okay talking about it, it could be good information for you to know, and perhaps it can serve as an opportunity to remind him that you care about him and if he ever would like to open up about it, you'd be happy to listen. I'm not sure if you have to worry much about making him feel emasculated. Like someone else mentioned here, you know him best, but perhaps if this is a concern, you can somehow remind him, maybe by example, that vulnerability can bring you both closer together. Plus it's 2019 - more and more guys are cool talking about sensitive issues.