I don't know if this is an option but I like talking while wine tasting. If you pick the right place (Coopers Hawk works well for me) there's just enough noise and distractions that if you need/want to change the topic, easy. If you want to go deeper into a topic, go for it.
Not only that but we've met a lot of interesting people that were fun to be with. To answer your question, I agree with Rachel Lynn, just tell him.