Diary of a Forever DM

So I’ve been wrestling with the idea of where to start with all this, and I finally figured I might as well start at the beginning. That is to say, the beginning of my D&D journey.

Back around 2016/2017, I was working as a house manager at the local theater. I’d graduated from college in Spain about a year or two prior with an acting degree, and I was struggling to find myself and my place after moving back to the U.S. Acting work wasn’t exactly easy to come by, so I was making do with house managing, teaching theater, and performing as a princess at birthday parties.

I was also struggling to reconnect with my friends in the U.S. I’d only really maintained contact with four of my high school friends, one in particular being my best friend—we’ll call him Tim. We’d been best friends since middle school. We were so close that everyone always thought we were dating, which the two of us found very amusing, as we were most certainly not.

When I moved to Spain for school, we maintained our closeness. We talked every single day and had lengthy video calls once or twice a week for all four years of my college career. We didn’t let the distance or six-hour time difference stop us from constantly talking to one another.

Unfortunately, during those four years, our relationship spiraled into a toxic mess. A codependency of sorts. To put it plainly, I always expected Tim to be there to talk to me, be my emotional support, have a laugh with me, etc., whenever I needed him to be—and he expected the same of me.

Now, you’d think that being in different countries would make it easy to excuse or justify when that wasn’t possible on either end, and yet it didn’t stop us from having massive blowout arguments about it. Arguments that I now realize stemmed from my frustration at having to carry the bulk of the emotional weight in our relationship—and from his inability to properly communicate or express his apathy and periodic emotional detachment to things (me in particular).

We struggled to find the balance between desperately wanting to spend time together and living our lives out in different countries following very different paths. I constantly juggled a billion and one things and always wanted to do and try more stuff, and he would find that overwhelming or overstimulating and become apathetic in response, which would drive me nuts.

Not only that, but we were also incredibly jealous of other friendships/relationships the other had. (Yes, I know we sound like a toxic couple. I assure you we were toxic, but also entirely platonic—neither of us was romantically invested or physically attracted to the other.)

I’d started a very deep—and also platonic—relationship with one of my classmates in college, and any time I wasn’t spending with Tim, I was spending with him. Tim would get jealous any time I couldn’t get on a Skype call or respond to a text because I was out having fun with this other friend.

Tim, on the other hand, had started dating this (in my humble opinion) abusive, manipulative, arrogant a-hole. We’ll call him “B” for Butt-face. Is it clear yet that I hate this person? I absolutely loathed him and their relationship with every fiber of my being. I hated seeing B mistreat Tim—gaslight and manipulate him. I hated that no matter what B did, Tim still wanted to be with him, and I hated that Tim would always cancel plans with me if B hit him up.

I’d put in a lot of time and effort into our relationship, and it felt super shitty to play second fiddle to B, when he was such a bastard. Tim and I argued a lot about their relationship. Granted, had B been a decent human being, I may have felt differently, but alas, he was not.

Regardless, as my college years passed, Tim and I began getting into more and more arguments. We had lengthy fights all the time, we bickered back and forth constantly, and it felt like neither of us was willing to budge or give the other any ground.

By the end of my senior year, I was certain that all we needed was to be in the same place again. Once I moved back to the U.S., we wouldn’t have to fight over scheduling or time with one another. B was supposedly out of the picture, since I’d gotten the two of them to finally break up a few months prior, and we could just go back to being best friends and hanging out all the time.

Boy, was I wrong.

When I came back in the summer of 2015, the arguing just escalated. We’d find time to hang out, and then he’d blow me off for people I’d never even heard of before—or worse, TO SEE B! It blew my mind and infuriated me to no end! After everything he’d been through with B, everything I’d done to try and fix and salvage our relationship, I was still second to this idiot!

It felt like Tim never made time for me, and I always had to jump through hoops to spend time with him. I didn’t feel appreciated or respected, and I was starting to doubt that our friendship would ever recover. Granted, I realize now that he was probably avoiding me a lot of the time because whenever we did hang out, I’d usually end up chastising him about something, and he simply didn’t want to bother with it. But at the time, I just felt neglected.

Now fast forward to the start of this long-winded story:

I’d been back for a year and a half or two years, and things between Tim and I had just continued to deteriorate. We still had fun and an incredible time with one another when we weren’t fighting—but we were fighting more often than not. It was exhausting and emotionally taxing for me.

Tim and I were so intimately close and understood each other on such a deep personal level that losing that relationship felt like losing a limb to me. And I couldn’t understand why we couldn’t fix things. Like I said, we understood each other incredibly well—to the point where it might have seemed overbearing. I knew he understood that I was being hurt and upset, because I was constantly telling him so, and yet he still refused to meet me in the middle and change behaviors that I found intolerable.

I’d spent years fighting for us—trying to repair the damage between us, swallowing my pride, and extending the lengths of my patience to limits I’d never reached before and haven’t reached since. But Tim wasn’t putting in any effort on his end. If I told him something upset me, he’d just go and do it again. Hell, getting him to genuinely apologize without coaxing it out of him was nearly impossible.

Which baffled me, because I knew he cared about me and didn’t want to lose our friendship—but he refused to fight for it. And I couldn’t understand why. Why the apathy? Why did it seem like he was fine with hurting me? Why did he feel like it was my responsibility to carry the weight of our friendship?

It became clear to me that he was taking me and my patience for granted. Like he knew that no matter what he did, I would always find it in me to give him another chance. And he was right—but I was at my wits’ end.

All that to say, I was in a pretty isolated and dark headspace. I was working at the theater, struggling to feel fulfilled in my career and my friendships, and just generally feeling alone.

That’s when one of my coworkers—we’ll call him Bob—started talking to me and clearly wanted to be friends. Normally, I would have had an aversion to getting close to him because, from past experiences, I’d found that nine times out of ten, a guy who became my friend would end up catching feelings, and I’d have to break their heart and reject them. (I have a hard time being attracted to people.)

This would inevitably ruin the friendship, make things weird and awkward between us at work, or—worst of all—turn them into yet another stalker I’d have to deal with. So I tended to keep my work relationships strictly professional. However, I was so incredibly lonely that I decided to give Bob a chance.

He and I became work friends fairly quickly, and one day he asked if I wanted to come over to his girlfriend’s place after work to play Dungeons & Dragons with them and a few other coworkers. I’d never played before, but I’d always been interested in it. My uncles had mentioned playing when they were kids, so I kind of had an idea of what the game was about.

So again, I ignored the instinct to say no and keep our friendship restricted to work, and I took him up on his offer. And I am so very happy that I did—because it completely changed my life…

Which I’ll elaborate more on next time. My ramblings have gone on for much longer than I intended.

I realize that this post is more about Tim and me than it is about D&D—but that’s okay. You see, Tim is a very integral and important part of my story and (spoilers) currently a player at my table. So this is all relevant, I promise.

Next time, I’ll dive into my first D&D experiences and how they set up the groundwork for me to become the story-driven, fearsome Forever DM I am today. I also have a billion and one stories about Tim and me, so if anyone is interested, I can always elaborate more on those.