My first time playing Dungeons and Dragons was not what I imagined.

I had heard of Dungeons and Dragons in the past, but I didn’t know of anyone who actively played it. Mainly, it was a game that was mentioned in a show (shoutout to Stranger Things) or movie that added to the fact that the character at hand was already a nerd and/or outcast. I, like so many others, grew to associate it with nerd culture. But not modern, “Comic Con”, trendy nerd culture...the kind that the loners with no friends played in their mom’s basement with Doritos strewn all over their laps. That could not be more far from the truth - except maybe the Doritos bit, because everything is better with snacks.

I was truly introduced to D&D when I met my current partner. From our first date, they mentioned their love of D&D to me after I opened up about my own Harry Potter obsession after dipping into the 3rd bottle of wine (hot first date topic, I know). The more time we spent together, the more I learned about D&D, and the more I learned about their passion for it. As I heard more about the game and flipped through the starter books, I knew it was something I wanted to try. The art was beautiful, the mini’s were awesome and I had gotten to paint some, and I really felt like it was something that I would enjoy doing. But, I was also super nervous about giving it a try for the first time because I, the queen of introverts, quite frankly wanted to vomit at the idea of sitting down at a table with strangers and talking in funny voices. I still didn’t quite understand what actually playing entailed. “Roleplay” was the main word that was given to me to describe it, but when I picture roleplay, I picture a bunch of people dressed in medieval garb going at it in a park.

Being so intrigued but still intimidated, I finally said “ok” and sat in on a session that my partner played in and, well, I understood...but honestly wasn’t impressed. It was helpful to see that it wasn’t quite LARPing - it was instead 4 - 6 people sitting around a table, in their regular clothes (or lets be honest, tacky but wonderful D&D shirts), rolling dice in fancy trays and playing a character they put a lot of time and effort into creating. I only sat in on the first half of their game and decided not to watch the rest after they took a break just because it seemed like a lot of time to put into killing a single bad guy. We discussed what I sat in on after and I was assured “it’s all about finding a Dungeon Master that you like and no DM is the same.” I still wasn’t sold, but their friend had just started his own campaign and I knew this was important to my partner, so my decision to play felt like it was now or never.

Kahli, Caia’s first character.

Kahli, Caia’s first character.

Together we sat down and went over character sheets and I spent a couple of hours creating my first character, Kahli; a Rogue Shifter with murdered parents, their killer still chasing after her years later, and a bit of extra body hair. I took my time creating her and was taken aback by how in depth character sheets are. As someone who likes to write, this was the most incredible tool to create with and I was so impressed by what is provided to help you create. I had no idea how much thought was put into the characters people played with. I spent another hour creating Kahli’s backstory, deciding exactly what she looked like, and imagining what kind of personality she was going to have. My partner and I went out to buy my first set of dice the next day and then I found myself at the table on a Wednesday night with sweaty palms and a shot of liquid courage in my system, ready to go. After a recap from the DM and about 5 minutes of play, my character was peering over a rock at the rest of the party and I was put on the spot to start describing who I was and start playing her. After the initial shock of “Oh shit, this is it” I spoke my first lines, and to my surprise, it flowed so much easier than I thought it would.

Now, to be fair, I still wasn’t sold on it after my first session. I really struggled with the actual technicalities of it and found myself dwelling on what I did wrong after the game and still do after nearly 20 times playing. I still struggle with which moves to make in a round of combat and which you can use and when. What’s the difference between an action and a bonus action? Can I use two actions instead? I am still HORRIBLE at remembering to check for traps and be stealthy. I’ve almost died twice in 12 sessions from scouting on my own; once from an elf with a poison dagger and another from a f***ing carpet (To my fellow new Rogues who don’t do well in close combat, DISENGAGE and MOVE AWAY first!!!). The DM took pity on me and had to step in to remind me I am better with my bow because he didn’t want a rug to kill me (The real MVP). I forget to bonus action. I forget I can sneak attack (which is the whole damn point of being an Assassin). We joke that I need to start writing down “SNEAK” and “CHECK FOR TRAPS” on my hand before the sessions start to remind me (Spoiler alert, I did. It helped). Although this can discourage me from time to time, I know practice will help and I still have so much fun playing otherwise.

Down the line, I joined a second campaign with a different DM as Olga Whetherby, an ugly, ginger, Barbarian Mountain Dwarf who needed to fuck everyone (with the blessing of her dead husband who came to her in a dream and told her to keep making love), and I took a stab at doing an accent (which somehow came out as Russian). I had SO MUCH fun playing her because she was raunchy and completely out of my comfort zone, but ultimately I stepped away from that game because I joined it 42 sessions in and I was having a hard time keeping up with everything the party had already gone through. Also, stepping in as an 8th level character after I had only played D&D four times was a huge struggle for me, but it was definitely nice to not fear that I was going to constantly die with 122 hit points instead of my Level 4 Rogue with 27. Scratch that, the DM had us fighting things that almost made us die constantly and had us facing the potential end of the world. Yeesh. I felt like a newborn baby fresh out the womb getting stomped on in that campaign and had to thrown in the towel.

Overall, I was happily surprised to learn what D&D really is and I learned quite a few things that I think is useful to pass onto first time players:

  1. A LOT more people play this game than I would have expected. After mentioned I started playing with my partner, I learned that I had 6 friends that played it. On top of that, my parents friends had played it. Some of my coworkers. I had no idea how common it was.

  2. The people at your table are more than happy to help you. Use them. They are your best tool. They had to play for the first time once too so they know you’re not just going to sit down and get it. If you’re confused, ASK. If you want to do something but aren’t sure if you can, just ask your DM, “Can I do this?” That’s what the DM is there for. I figured I would have to know what I was doing right away and I was so relieved to find that everyone was ready to jump in and help me with my sheet and calculating my attack points. If you don’t feel welcomed by the group of people you’re playing with, find a new group.

  3. Love thy DM. The amount of thought and time they put into running a game is insane. A good DM is basically writing a book for you and creating content that is outside what is provided in a guidebook. They are putting in the hard work to make sure you have an amazing time every week and some people do not realize how much it takes. Listen to them. Respect how they want to run the game, and if you disagree with something, talk to them after instead of making a scene during the game. Be respectful to everyone.

  4. Do what you’re comfortable with. Did you commit to an accent in the first game that you wish you hadn’t? Tell your players you don’t want to do it anymore. Are there some people at your table that are heavy roleplayers but you’re not comfortable with it? You don’t have to roleplay. You can approach the game in whatever way makes it the most fun for you. If there’s ever an aspect of the game that you dread going into it, figure out a way to change it.

  5. You DO need that many dice if it makes you happy. They’re soooo pretty. Or mini’s. Or terrain. Hey, it’s not drugs, right?

  6. Don’t ever continue in a group if it feels like a chore. If you aren’t having fun, you aren’t obligated to stick around. I feel extremely fortunate to be in the group I am now, especially with it being my first time being really invested, because of the connections we have made and how we all play in a similar way. If you haven’t found your people yet, don’t be discouraged. Keep looking. There are great ways to find people online if you can’t find them in person or you can always check out a local game store that runs games.


So if you’re considering playing for the first time, just do it. Did you try it and don’t think it’s for you? Don’t play! Don’t think you’re good at it? Most people probably aren’t their first time. Dungeons and Dragons is an incredible adventure I encourage everyone to try at least once.

May all your rolls be 20s.

Yours truly,
Most Likely To Die


Meet the Blogger

Caia B. @caiawazlib

Caia is an avid reader, writer, and Potterhead. Outside of business hours she can be found on the patio with a glass of wine, petting her pup and 2 cats or in her boyfriend’s D&D dungeon rolling dice.