Yes you can do! Surprised but yes while you answer any question and find there some one you know, you just comment on and get answers again you do comment and thus you can chat with them regularly choosing the same question and going to its comment box again and again.
Ask.com does not support this feature but you can comment on something they've answered. The reason why you can't message people on here is because Ask.com is more of a Question Answering website rather than Facebook, Twitter, etc. websites. But, if you have any suggestions that you believe can improve the Ask.com website please do so and you can at https://www.research.net/s/askdotcomfeedback Hope that helped, Your Welcome and have a Wonderful Day :D
When someone comments on anything I've posted, including my questions, comments, and answers, I get a message that says they have done so. Is that what you're talking about? Also, if you follow someone, you can click on their icon and you'll be taken to their page which lists recent questions and answers they entered.