You can ask, he just will not answer is all. If things are not "okay" with him he will tell you right then and there, there is no galactic "okay" that stays constant.

You cannot control someone else, make them reassure you; you can ask for whatever you want but cannot make someone supply whatever it is; in fact, reassurance is impossible for someone else to give you because they are not the ones without the assurance, you are so only you can supply it. How you feel does not come from outside of you so outside sources cannot "fix" whatever feels bad.

To start, I would try to take reassurance from his not saying anything is wrong! Ask yourself, "is everything okay?" and then answer, "Well, T hasn't said anything was wrong so. . ."