One of the hardest things I had to do as a new DM was run the first session for my group.
This was to be my very first time DMing for real (playing about as a character and a DM for the Starter Set didn't really count considering we had no idea what we were doing and there was only the 2 of us!), so I was extremely nervous and had absolutely no idea what was going to happen.
I'd done all of my worldbuilding, and the players had already created their characters, with rich backstories full of hooks I could use, so when it came round to the day, we could jump straight in. Great! Or not, depending on your point of view, but either way, the time came and I was nervous.
Luckily, it all went extremely well - everyone had a good time and enjoyed themselves, which is all you could ask for really. I was still worried about everything I had done.
In my opinion, the first session of any group is the hardest thing to do. I don't want to railroad my players (this is a sandbox-style game after all, with a very loose overarching plot), but obviously there are certain assumptions that have to be made and certain things have to be forced into existence (I mean, what really are the chances of 4 different people of different races all being in the same tavern in the same town?).
It worked out for me in the end, because all of their backstories made a lot of sense - one of the party was a member of the Thieve's Guild, one had abandoned his education at the Mage's College, one had run away from home after his parents died and the other was on a quest to find his long lost father. In the end, we all agreed that the player from the Thieve's Guild hired these adventurers for a job near Shadowley, towards the North, North West of Asparia. As much as this solution worked, I still couldn't help but feel like I'd forced the players (and their characters) into a situation they wouldn't necesserily have been in (but hey, your party's got to start somewhere right?).
The rest of the session involved the job for the guild going haywire; the character had been betrayed by the guild and played against another member. However, one of the things that struck me again - why would the party stick together? Obviously they will, we're a D&D group sharing an adventure, why would this person's character suddenly go back to a mundane life? Even so, this is another problem I've faced - the reasons for the party sticking together.
That avenue is still being explored, but since then we've had 2 other sessions and I've managed to make it so certain events have kept them together as a unit for now, but I'm sure in every group there comes a point where the players, and their characters, must make choices and determine the reason the group stays together.
What really helped though was Mia, who plays a Merfolk Barbarian, rolled for her character's "length and girth". She rolled a natural 1.
Anyways, that's my rant over - all I'm trying to say is that the first session will always be the hardest, so don't be afraid to be honest with your players. If something doesn't work the way you planned, tell them and make a decision (especially if you're a new DM playing with experienced players like myself), they're bound to understand.
Good luck!
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