Dungeons & Dragons Online

I helped one of my players propose IRL to another player during a session.

Back story

Several years ago, I started playing D&D with a few co-workers, one of them (I’ll call Tom) was DM. We played Tomb of Annihilation. It was all very loose, casual, and good times were had by all. Over the course of playing for about 9 months to a year, we added a few more co-workers including one (I’ll call Gwen) who was brand new to TTRPG and at the start, was just showing up to get away from a husband she ended up divorcing. D&D was a whole new level of geekdom for her, and she got some surprised reactions from people in her life when she told them “I’m playing Dungeons & Dragons with a bunch of friends I work with.”

I don’t remember the exact timeline of events but after Gwen started playing with us, Tom got a new job, Gwen got divorced, and later began dating Tom.

We eventually locked down consistent group that seemed to mesh well. Our campaign that started with Tomb of Annihilation was getting a little aimless, so I agreed to be DM for my first time, and in November of 2019 we started an Eberron campaign right around the release of E:RftLW.

A year into that same Eberron campaign in December of 2020, Tom tells me he wants to propose to Gwen during a session. He was hoping to propose in Feb/Mar 2021, so he gave me plenty of notice to plan something, which really helped me prepare what turned out to be a great experience for our party.

The proposal

Our party, which had spent most of the campaign in Breland, needed to travel to Valenar for an arc. I knew they would enlist a magically adept NPC to teleport them. I used this opportunity to logic this NPC wasn’t familiar with Valenar and the teleport “rolled” an off target success. The spell dropped them in Taer Zanathar which they were able to identify from geographical landmarks (Mist Wall to the west, ocean to the south).

I described a small, abandoned town around the ruins of a large tower (the Taer). As they moved through the town, they saw quite a bit of ghost or spirit activity that was leaving them alone for the most part. They happened on the ghost of a small elvish girl who was crying. She tells the party her parents are trapped and can’t take care of her. The party is lead to one of the larger houses in the village. After waiting a bit, they see the ghosts of a couple appear, talking about a surprise waiting inside.

I played it that this couple was stuck in a time loop with them re-playing little echos of time in each room in the house on the day of their engagement. Little clues of somewhat cliché marriage advice were in each room with a simple puzzle to solve.

One example: On the table there is a pitcher of water and two cups, and a card. You see the ghosts appear, looking around. The woman picks up a card on the table. "As you journey through life together, always seek out ways to serve each other. Service strengthens all bonds. A simple act of service is all that's needed to resolve some issues, like lighting the torch.

And all they had to do was pour each other a glass of water to light the torches. Pouring water into your own cup makes the water disappear.

This was a large house I had designed with some dungeon craft maps with about 9 rooms in total. The last one they discovered was an underground cellar with two sarcophagi in it. When they party enters the room, I tell them “You see the couple appear in this room and the male drops to his knee and says…” and I stop talking and look at Tom. It takes a beat for everyone to shift their focus from me to Tom as he gets off his chair, down on one knee, which finally gets a reaction out of Gwen “What is happening?!?” Tom managed to get through proposing and got a “yes” from Gwen after a good long pause. It was during this pause I had the perfect view of our whole party, jaw dropped and absolutely stunned in the moment. I will never forget their faces, LOL!

We took a few moments for some drinks to celebrate. Came back to the game and fought the bad guy that was keeping the ghostly couple in the time loop (which I decided was Death Kiss accompanied by some stone golems (other statues in the room). Turned out to be a great fight. By the end 3/6 players were within one hit from the death kiss of going down.

Tom tried to setup a recording just before the “proposal/coffin room” with his phone hidden in the corner of the room. But it fell face down before we got there. So, he has an audio recording of it.

During all the marriage advice puzzles, Tom was worried I was being too heavy handed and was going to give it away, but Gwen didn’t see it coming. Neither did anyone else in the party. I had disguised it in the setting well enough that none of them thought there was anything above the table going on. This brought me great joy to learn after the session.

We are still playing the same Eberron campaign. The party is currently level 11.

Tom and Gwen are in Las Vegas right now getting married tonight. I’m super excited for them, wish them the best in their life together and look forward to our many years of D&D to come.

Congratulations to them on their wedding day!


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