For me, one of the worst feelings is knowing that I am creating tension / making someone uncomfortable by the way I talk. So, my advice to you is to treat him as you would any other person. If he is struggling with a word, **maintain eye contact (don't deflect by looking away), and do not finish it for him**. Your mannerisms while he is speaking will tell him how comfortable you are around him. If he's struggling with a word and you begin shifting in your seat, looking around, or finishing his sentences, he'll know he's creating tension in the conversation. Unless he brings up the fact he stutters, don't talk about it and pretend like he doesn't have one. Perhaps if things work out and you two continue seeing each other, he will become comfortable enough around you that you can ask him questions about his speech, but for your first date, leave it up to him whether he wants to talk about it. Once he realizes that he can stutter freely around you, he will immediately become more relaxed and open. Trust me, he wants to talk to you until he's blue in the face, but he wants to make sure he's comfortable enough around you to do it. I have friends who crack little jokes when I get stuck on a word or finish my sentence, and although they are still my friends, I am considerably less open to them than I am to other friends who don't take notice of my stutter. Tl;Dr: Show him you don't give a shit that he stutters by remaining calm and collect while you speak with him. Let him finish his sentences and stutter freely around you. The more he talks, the more comfortable he will get. P.S. It's awesome that you find stutters somewhat attractive. I've always thought people found them weird and unappealing. You've sparked hope in me!