I'm on the 360, and whenever I talk to him, he doesn't have any dialog option, so I can't get him to train me in speech, which is weird because I got him to train me not too long ago. And I didn't do that quest that involves him, which I heard may be the reason for this, nor do I even have the quest unlocked.

What time of the day is it? Trainers sometimes offer their services at certain times of the day.

I forgot to say I found out the problem. it was because my speech was over level 90, and I didn't realized the cap for trainers teaching you was 90. It's level 100 now though.