I Didn’t Have Fun And I’m not sure Why

WARNING: LONG. (TLDR at the end)

I’ve been running an online game for two of my friends for about half a year, the first arc of which has recently wrapped up. It was a slow-burn mystery, but I had started that game at a time where I didn’t understand proper pacing— as a result, they spent half a year at 2nd level trying to figure it out.

Near the end, I realized this, and ramped up the pacing to compensate. They solved the mystery a couple weeks ago, and though it was satisfying to finally see the villain go down, I learned from my mistake, that I shouldn’t have drawn out an arc that long.

With that out of the way, we decided to have a Christmas break from dnd, and start the new arc in January. Two players were going to join us in the new arc, and an old one that hadn’t played for a long time was gonna return to the game as well, so we’d finally have more than two people.

But one of my players was (and currently still is) extremely flaky and bad at communication. He constantly wouldn’t show up for sessions, and when he did he seemed bored and disinterested.

Maybe two sessions ago he did actually show up, and seemed to have fun. It seemed to me due to the amount of combat in that one. The future looked relatively bright from a DMing perspective.

(Long sentence warning) But that same session, in the second half, they were in the middle of a revelatory scene where they were discovering why the villain did what he did, who he worked for, etc. when he straight up dropped out, said ‘he didn’t feel like playing dnd’ and started playing on his PS4. We had to do the rest of the session just one on one with my last remaining player.

TL;DR this one guy was extremely flaky, I tried to reconcile this several times, tried to communicate with my player, sent dozens of texts, to no avail. When he would respond, his messages either monosyllabic, or cryptic phrases with little to no context. And it was killing me.

BUT… there’s some context, which I thought could help somehow.

I persevered. I said, okay, bro, you can play it like that. But you’re missing out.

Last night, we had the second session of the new arc. He didn’t show up, which didn’t surprise but still tortured me, because all he had to do was say a couple days in advance he couldn’t do it, and I’dve been alright with that.

But besides, it’s cool. We still have the dude that’s been here from the start, and two new players. And a fourth on the way story-wise, about a session or two away.

We used this session to long rest, and have a fight with a swarm of goblins, which took up the second half and wasn’t finished cause it got too late and we had to end. They didn’t make much progress, but it was neat anyways.

This morning, I was hit with something unusual. When I was reflecting back on that nights events, I didn’t see them as particularly Fun.

Which is really odd. Cause at the time, it was a action-packed fight, and my players said they were enjoying it (even though they were getting their asses handed to them by these goblins).

But when I look back at it— I don’t think I had fun. And I’m not entirely sure why. Partly cause there are so many factors that could’ve made me feel this way.

Should I have had that fight at all? That’s practically all they did the entire session— maybe I should’ve just let them pass through and get to the escape route, rather than having the story grind to a halt— or did the action actually propel the story forward?

One guy was having trouble deciding what to do in combat— Had I felt like I needed to babysit for him? Or maybe it had something to do with that flaky player not showing up, somehow? Maybe it had finally worn me down?

Or perhaps, the fact that they had been in this same darn village too long, and I was just bored with the plotline that I had set up? If it’s that case, should I just wait it out and see the new arc unfold, which would be next session, or discuss with the players about if they’d want scrap the campaign entirely?

Or maybe I actually did have fun, and my brain is just out of whack this particular morning?!?

TL;DR I don’t feel like I had fun as a DM that night, I don’t know why, and I don’t know how to fix it. Also, I think I need advice on how to deal with this flaky guy.