With so many people having problems with dialogue being lackluster or pointless, i have some suggestions to improve it:
1. Reduce chained skill checks. As mentioned before, it's pretty dumb when you successfully pass a check and it does absolutely nothing but make you roll another check or 2.
2. Have a warning to any hostility. There are too many responses that sound harmless enough, but instantly cause the NPC or group of NPCs to turn hostile and attack right away. There really should be a warning of "tread lightly or we'll attack" type of dialogue line before those. Perhaps even a notice in dialogue choices themself, adding a (hostile), (friendly), and (neutral) option next to each one to guide us on how we want to RP our character.
3. Rewards for succeeding in avoiding fights using skill checks. Maybe a little XP, some random item, whatever. Combat itself is always rewarding with XP, but dialogue skill checks are by far harder to do and should have some feeling of reward for it. Personally I feel my characters would become strongest just by killing everyone and avoiding these skill checks altogether, none of it seems rewarding especially with multiple checks needed in a single conversation.
4. Natural 1/20 criticals on skill checks. If there absolutely has to be more than 1 skill check roll, at least make it where a natural 20 makes it awesome enough to cover all and maybe a natural 1 instantly the worst outcome. The skill check rolls just don't feel DnD enough without the criticals.
5. Group party involvement. Every conversation that your party is at, they should all be a part of it and contributing. If a party member is more liked than your main char, they should take over. If a party member has a better bonus to a skill check, they should automatically be the one rolling for it. It's very tedious having to micro manage individual characters for dialogue they should all be a part of.
At least this could be a start, some may want more substance and meaningful bits of story and lore, which would be nice, but at least take out the annoying parts killing the fun in talking to every NPC you come across. For many years I've had a habit of talking to every single NPC i come across for lore, hints, guidance, side quests, etc. Because I worry about skill checks failing and causing fights now i tend to not talk to anyone i don't need to lol, or at least quicksave before every single dialogue which is also kind of annoying.
