Hey y'all, I've been thinking about this for a while and I was wondering if there was any advice here, perhaps people who have been through something similar.
I've been DMing 5e for a while; I started maybe 7 or 8 years ago in college. I ran LMoP for my roommates to begin, and I had a campaign that lasted two semesters for a different group of friends. That second one was super homebrewed, and hugely successful in that it seemed like everyone had fun. But throughout that campaign I realized there were a lot of things in my game I wasn't satisfied with, especially in regards to combat and the "difficulty" of the game. PCs blew my encounters out of the water and took long rests whenever they felt like, and I wanted there to be stakes, dilemmas, etc. That stuff has been pretty widely discussed online and I have learned a lot since then.
Since then I've only had one group stay together for a reasonably successful campaign, and I thought I could do more or less the same as I had done before, but better. I had one player from the previous campaign as well, which I thought would be a boon. He's my best friend and I love the guy, but I realize now he just doesn't like the way I have evolved my DMing. He doesn't like how there's not always time to take a long rest or fighting without all his resources, he doesn't like encounters more complex than running into the fray to swing swords and cast spells, and he doesn't like that the characters might die now. He's been pretty open about this, and he's told me that in his opinion, the way the game should go is the players face some obstacles but they overcome them, and it's unsatisfying if they don't, and character death is unsatisfying and unfair, and imo if I read between the lines he basically wants to be able to run his warlock into an Annis Hag and know that he will come out the other side alright.
To be clear, this isn't a bash-my-friend post or a problem-player post, I appreciate his honesty and how he knows what he wants from the game. The problem is I am having a lot of fun with the things I've learned, and I don't wanna go back in the playhouse. So the question is how do I handle this and AITA? Would I look for a new group, or is that me thinking the grass is greener with folks I don't know very well? I don't want to run a game that my friend will get tilted in, but I am so bored with running simple encounters that get exploded by a party that gets a long rest between every fight. Help please.
Adjusting the game to fit your table is the hardest challenge of all unfortunately. There are some players who don’t fit certain tables and DM styles and it’s your job to either make it work or tell them to find another table.
I think in your case you can make it work, but you’ve got a lot of work to do since you’re trying to accommodate a carebear happy fun time player at a table you want to run more and more as “hardcore-lite” experience.
I think two ideas I would have for you are to present your hardcore challenges as optional / non lethal challenges in a arena type colosseum. This lets you design difficult encounters but sandboxes them from consequences. If you want there to be consequences you’re going to make the carebear sad.
Another option is to come up with a McGuffin for the carebear that acts as protection for their character. E.g they fail there death saves and they turn into a rampaging monster due to some story reason. Lots of bad things happen to the party, but carebear wakes up the next day fine. You can use this to change the dynamic of “carebear” go frontline while we hit badguy. The big problem here is protecting the carebear leads to possible resentment from the other players so doing something like this is dangerous overall, but it can work depending on your players and how you do it.
For a TLDR I think you want to run more hard core games and your “carebear” player no longer fits at the table you want to run. In short you have to accommodate the “carebear”, change their mindset, or create a table of people ok with a more hardcore game.