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Saymore levels up from time to time when you do. You don't need to have discourses with him.
And yes, nobody wants to "fight" you, because your level is too high.
Every Discourse there's a chance he'll gain a level if he can. Usually anywhere from 0-2 levels per Discourse, depending how far away you are from his level.
I think the fact that the "Seymour gained a level" popup and noise happen when you fight him and he gains a level, but don't happen when you fight someone else and he gains a level anyway, subconciously convinced me that fighting other people obviously wouldn't work.
In Chapter 1 (and for most of the game), Boasting will refuse to engage you at all. S t r a n g e l y enough, you won't even be able to Discourse him once level-appropriate. He has an interesting level formula - his level is equal to Whitty's unless she's 31 or lower, in which case he is level 32. So in the final chapter he becomes available as a high-level, high-skill challenge with exceptional AI and a formidable and balanced unique advantage, then tailors to match your raw power all the way up to the level cap. He thus gives out more experience than any other character in the game, upon defeat, so sparring with him will allow you to max out your level bows and purchase anything you might still need.
The General is available in every chapter EXCEPT the first, but by the time you are no longer at a significant disadvantage to Boasting, she will quickly fall so far behind you that she becomes unavailable in the later chapters unless you're deliberately rushing through at a low level. She is thus a middleweight by design, who will challenge you significantly through your upper single digit levels through your teens, becoming more of a punching bag in your twenties before disappearing entirely.
The Boxer STARTS the game as the lowest-level character besides Whitty and Seymour, but ENDS the game stronger than any of the "normal" characters except Boasting and, if he's fully developed, Seymour. He's similar to the General but lasts longer because of his higher level cap in later chapters and has a more prominent role in Chapter 1.
Mew will only Discourse you during the final chapter. She's more of a joke character, since she grants no experience but only a bow and a necessary part of an achievement.
I can't remember if Seymour will still discourse you if he's at his level cap and you're at Whitty's (40), but if not he'll get you almost the whole way there. On your first playthrough he's one of the weakest characters because of his level caps, but on subsequent playthroughs his level tracks Whitty's largely without restraint if you Discourse with him frequently. This allows Whitty and Seymour to be some of the most powerful people in the room on New Game+, if you choose to play them that way. (I love to play them that way.)
Prattle is quite interesting - she starts the game as the second-most powerful person in the room after Boasting, but has the most modest level growth of anybody. If Seymour is developed much, then she ends up the weakest of everybody, and can be level-locked permanently by the second chapter if you grind enough. To me that always felt like commentary on her character - her heavy-handedness diminishes even her high social station, while the young boxers humility, charm and patience make him more upwardly mobile as he learns all he can from Boasting.
Boasting, well.....his specialty is opening-move advantage and level advantage, and without getting into spoilers, that figures nicely into how he ends up engaging the plot.
Every character is not equally relevant in all chapters. In Chapter 1 you should be dealing heavily with Seymour and the boxer. In chapters 2-3, you should be dealing Discoursing with all of the humans except Boasting. By chapter 4, Prattle and the General should be falling off of your radar, and Seymour will only be able to keep up if you upgraded him aggressively and sparred with him frequently. (His upgrades carry over betweeen playthroughs, so this is very easy on New Game +). In Chapter 5, even the boxer will likely be level-locked, so your final partners will be Judge Boasting, Mew the cat, and possibly Seymour in his ultimate form - in essence, the real heavyweights in the room when all pretense is stripped away.