I am starting to think there needs to be a back and forth in my story, between my character and someone else so he has someone that he's telling all of this too (before it was just a journal but that wasn't working). I am thinking it could just be a teacher, and I have experience as a teacher, so that really isn't all that difficult to imagine what a teacher might say or think or do. What I am struggling to figure out is how do I make the characters sound different enough (without the going "Don't you dare read this Mrs. Dunphrey route and have him write it without every expecting a response), when it's still me writing (very novice writer lol). Any ideas?
Are you actually writing from two different first person perspectives or do you mean how do you make dialogue sound different? I agree that it can be really hard to make two voices sound very distinct. I've said before, I think Nick Hornby masters this really well in A Long Way Down, as it was something I hadn't thought much about before, so check that out. Also think about different dialects and slang - if it's a teacher / pupil difference then what colloquialisms will have changed between generations? How emotive are they both when they talk? What are each of them trying to express - e.g. the teacher may want to draw out emotive language from the pupil without revealing their own emotions. Listen to people around you in everyday life and really listen for different phrases people use, how much they pause, how fast they talk, how long they take to get to a point. Then apply it.
I tend to use things like dialects and work usage to separate my characters. I make lists of phrases that each one say often and ones that they never say. I also say embrace stereotypes. Canadas say "eh", jews say "oi", rednecks use strange contractions, new yorkers speak fast, teenagers swear, people who were kids in the 90s say "dude"... In Of Mice and Men, Lennie and George have some long two-way conversations but it's very easy to tell who's speaking because they speak so differently.
If you mean 'how do i make characters sound different', I second the first part of Jersey's suggestion. I have 3 characters who do the majority of my dialogue, though not always with each other. Mal uses a pretty simple vocabulary; he's just a soldier, albeit a damn good one. Zandakar's a bit more of a romantic linguistically, and his words have a bit more flow to them. Miranda has read a thesaurus, and likes to use big words where a much smaller one will do. Malchoir's sentences tend to be shorter, and he'd say 'very irritating' before he'd say 'infuriating' or use the word 'ire'. Zandakar would probably call the same thing infuriating, but might later say 'irritating'. Miranda wouldn't deign to say any less than irascible, and the idea that she ought to use more common words is nothing less than opprobrious.
If your characters are usually in the same vicinity throughout your story, I believe that you can follow the suggestions of the people above. Have different dialect for each character or have the way each of them speak be different. But say that your characters are far away from each other. You can try to change the perspective after each chapter. Like Character A starts on chapter 1, then Character B starts on chapter 2, Character A starts on chapter 3, etc. Haruki Murakami's book, 1Q84, has that type of perspective change, albeit the characters are very distinct in terms of their personality and the people they meet. Hope I was able to answer your question correctly