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Derpy's Reunion (The Time I Hit My Tabletop Player With The Feels)

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Awhile back I had the pleasure of running a one-on-one tabletop game with an online friend I made half way through 2019. I had messaged him after seeing some of his stories and art, and interacting with him in the typical way that a consumer interacts with a content creator. Telling him how good his art was, or making a funny quip about a joke in the comments of his story. I had seen several things in his work that indicated he liked tabletop games, so I invited him to a game I was trying to set up. After a bit of talking we hit it off real well, and are in the middle of a joint RP/story writing set up, as well as playing tabletop games when our schedules allow.

One thing that started this tale was the fact he and I started doing one-on-one tabletop sessions. We'd spend a few hours, time permitting, every few weeks or so, and just play out a story. Largely improvised, we would have a blast voice chatting and going through a much more story focused tabletop experience. He led the first session by GMing for me. My tomboyish mare, Ivory Fire hunted down a disguised evil necromancer in Celestia's magic school, and proceeded to bully him until the royal guard arrived to cart him to jail. I returned the favor by GMing a session for him, were in a griffin named Raven had to help Princess Luna steal a magical present for her sister on their 100th Gift Giving celebration. After that he offered to GM a multi session game were I play as Ruby Aurora, my usernamesake, as she tried to go on the high seas with pirate ponies. I knew I had to plan a special session for him, as his own schedule made it tough for him to plan out a full game. Enter in, Derpy's Reunion.


With Derpy being a favorite pony of his, I constructed an entire oneshot for him. The plot focused on Derpy going to an anniversary back at her old high school. Given her less than fond memories of the place, she requested that his character attend with her, as we'd already established Raven was a character that could get things done. Raven agreed to Derpy's request, since the mailmare had gotten caught up in the gift heist, and Raven felt a little bit of guilt. Just a smidge, I swear.

Entering into the school, and then the gymnasium proper, a cast around 15 NPCs could be seen milling about chatting, browsing the snack table, and catching up on old times. I had music playing ambiantly as the scene unfolded, the event DJ playing songs from when Derpy and her fellow classmates had still been in school. The tracks were partially taken from Messer Chups - The Incredible Crocotiger album, with the bass and synth really nailed that prom/yesteryear party vibe. The entire feel was aimed at evoking a sense of nostalgia, and that was only a part of it. When he started figuring out what the problem parts were, "That's Gilda, we should steer clear of her" and "Hmm anypony seen Rockerhopper? I heard she's supposed to be here, and I know that Gilda would want to hang out with her old chum." Derpy's wellbeing was the primary goal, though the ditzy mare seemed to let her guard down a little bit upon seeing some of her old friends, one from the drama club, and the other from her math classes.

That was when prong two of my nostalgia trip hit my player. I revealed a side quest that involved helping out the old school photographer find some photos he'd misplaced upon arriving back in town. Scattered throughout the school were polaroid pictures like this.


Made with some edits, the pictures of things that happened in the background of Derpy's school days was put into full view. And the fun didn't stop there. For you see, there was more than just nostalgia in the air. There was also a hint of love. Now, Raven's player is a CheerileeXBigMAc fan. With that I wove a drama of a most devious sort. Cheerilee, busy with her studies to become a teacher, had neglected the stallion she'd loved during their school days. Her introduction at the reunion was Raven finding her having a bit of an existential breakdown as she saw Big Mac, as well as Sugar Belle. With Big Mac seemingly having moved on, the school teacher was sure there was no chance for her to even say hello to the farmer without losing her composure. Raven stepped forward, and did the only sensible thing her chaotic good griffin personality knew how. She called Cheerilee a nerd, belittled her a bit, and told her to mare up. Giving her a pep talk, she helped Cherrilee look a bit more presentable by helping her redo her mane, and helping her find a better dress from the drama department.

But, as it seemed that Cheerilee had found the perfect wing mare (alright, wing Griffin if you wanna be pedantic about it) she remembered Gilda. Not seeing sight of Derpy, Raven raced out to find her. And find her she did. With Gilda and her cohorts having another crack at the mare by verbally taunting her and threatening to do some rather mean things. Not letting that happen, Raven thoroughly kicked flank, and dispatched the bullies, sending Gilda with her tail between her legs. One of the bullies, which Raven recognized as Rockhopper, a wanted small time thief thanks to her own dubious background, was placed into the one room that no troublemaker had ever been able to escape. Detention.

Leaving the criminal there, she gave Cheerilee another pep talk. she then got Sugar out of the picture by locking her in a broom closet (hey, I said she was chaotic good. She does what her gut tells her to). After a completely improvised exchange between Big Mac and Cheerilee, my player was satisfied in seeing them sit down and chat. Cheerilee just barely managed to not die of nervousness while Big Mac was his usual talkative self. With everything looking like the day was saved, what more could there be to worry about? Right? Well, remember how Gilda had fled after getting beat up? She had returned, with a single challenge. Meet her in the restroom, or Derpy would be humiliated like she'd been during their senior field trip to the royal castle.


Raven quickly accepted, and met the bully at the designated place. The muffled music of the gym was ever so slightly audible as they faced off. The whimpers of Vapor Trail, another reunion goer who Raven had left in a rather uncomfortable arrangement, i.e. with underpants on a hook, was the only thing they heard as they stood with bated breath. The fight was fairly one sided. Though Raven was quite the tough griffin, she was no match for the experienced talons of a bully such as Gilda. It wasn't until she received a swirly that Raven was able to at least try and fight back once more. Just as it seemed Gilda was about to dunk her head once more, Raven could hear a certain mare sneaking up behind the bully. With a quick yell from Raven to spur her to action, the cross eyed mare that had been belittled by the griffin did the one thing on pony would have ever expected her too. She wedgied Gilda. This act earned a meme worthy reaction expression of surprise/pain from the eagle faced assailant. That surprise was then leverage by Raven to beat the bully at her own game, and best her in their showdown.

And thus, with the day saved by the power of friendship and bullying the bullies, Raven got to finally put her feet up, and enjoy the final slide show that played the session to a close. All the while the photos she'd found around the school were put on the projector, and she got the hear the NPCs recall all those fond memories. By the end the lights all flipped on, and Raven said a final goodbye to all those that she'd met at the reunion, as well as gloat a bit to the bested Griffin and Rockhopper. As Raven left Yakford, the session drew to a close, and a tale full of memories, regrets, hopes and the prospect of many more stories yet to be told came to a close.


By the end, my player said he was shedding a little bit of a tear at how well the tone had gotten to him. He himself had never experienced a high school reunion, and felt it'd given him a second hand sense of what one might feel like (and I didn't point out a normal one probably would not have been as action packed). So there you have it. Using a combination of characters, music, and visuals, I was able to lay that sense of far off nostalgia of yesteryear upon someone that I am happy to call a friend, and who I hope to have many more stories told with in the years to come.


If you have any questions about stuff I might have glossed over, or want to share your thoughts on this whole wacky session we ran, feel free to reply. I always enjoy sharing my tabletop experiences with others (the reason why I wrote out all of this to begin with) and love to hear what others think of the insanity and hilarity I and my players get up to.

Also, I apologize if I posted this is the wrong section, I spent ten minutes trying to decide which one was best, before settling on this one, as it is a story, and the RP section is more for people searching for an RP.

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*thunderous manic applause*

THIS is the way a GM should be in a one-on-one.  Thank you for sharing your story.  :squee:

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4 hours ago, Randimaxis said:

*thunderous manic applause*

THIS is the way a GM should be in a one-on-one.  Thank you for sharing your story.  :squee:

Thanks, happy to be sharing it. I had a blast planning this out and running it for my friend, and like to channel the bottled up excitement a well run session gives me.

And if you couldn't tell, I tend to go all out with making handouts and character icons. You should have seen the Roll20 map that was made exclusively for this one-on-one. Not to mention this was edited for brevity, as Raven interacted with a few more characters that didn't quite land right, like the cult in the school basement xD

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