Jan 29

“My Favorite” part 3. by Caleb


Hello all,

Here is the third and final “MY FAVORITE” articles written by Guest Lecturer @theCalebg. In his first article, Caleb wrote about Conor, a  half elf, Neutral Good, cleric of Pelor, who was his all-time favorite character.  Next he wrote about his favorite DnD setting which was a home-brewed world created by the DM. Today Caleb talks about his favorite session of D&D. Please enjoy . . .



When it comes down to it, every gaming session has favorite memories and best moments.  There is always something amazing that happens that leaves players and GMs shocked and excited.  I remember countless sessions where a stunned silence fell across the table as the dice results settled over us and we realized what happened, which was followed by an eruption of exhalations and high fives.  I remember awesome moments when plot twists were revealed and major bad guys were exposed.

One of my recent favorite moments from a gaming session happened in the home brewed world I recently wrote about.  In this particular session, we were in the southern desert city of Rhugdon.  I was a human warlock and my friend was a changeling ninja.  We were infiltrating an enemy fortress in search of information about their attack plans and supply lines.  We had kept a low profile and had made some contacts within the enemy organization.  Our plan was to sneak inside the fortress walls when a shipment of food and wine was delivered for a feast.

But, as can happen, our plans fell apart.

We were in a tavern in the small city outside the fortress walls waiting for the shipment to be prepared.  A fight broke out between some of the tavern patrons and we stepped in.  The tavern owner was our local contact and we didn’t want things to get out of control.  However, the city militia had already been called.  The guards were employees of the enemy forces we had been sent to infiltrate.  We tried to stay out of sight, but I flubbed a roll and one of the guards recognized me from a wanted poster.  We managed to escape, but the tavern owner was arrested.

We decided to rescue him.  Luckily, he was only being detained in the city holding cells, not the larger prison within the fortress walls.  The ninja shape changed into a local thug and got himself arrested as well.  I created a distraction by setting the guards’ quarters on fire.  This gave the ninja a chance to free the tavern owner from his cell.  Unfortunately, a detail of guards arrived back at the exact moment the ninja was attempting to escape through the main holding cell doors.  With a quick shape change into a terrifying orc, he scared off a few guards.  Then with an incredibly lucky strength check, the ninja kicked the main door off its hinges into the rest of the guards and dashed away.

We regrouped, but knew our plan to sneak into the fortress was shot.  The guards were all on high alert, searching for us specifically.  Plus, reinforcements had been summoned from the fortress.  We decided to try a risky frontal assault.  This was absolutely crazy, as there were only two of us.  But we thought crazy just might work.  I took to the rooftops and started picking off the archers that patrolled the fortress walls.  I also knocked the large oil-fueled torches to the ground in front of the main gates.  My warlock had a bit of an obsession with fire.  As the guards scrambled to douse the flames, the ninja snuck through the gates and I climbed the walls with the assistance of my warlock invocations.

Now inside the fortress, we sped toward the main buildings.  The enemy leader had built himself a tower stronghold within the fortress walls.  We managed to get into the tower and up the stairs before the guards saw us.  Thankfully, the fire I had set was creating lots of smoke for cover.  The plans were in the leader’s main quarters which were at the top of the tower, naturally.  We found what we needed, but then got trapped in the room when the leader came in to prepare for the feast.

At this point, then ninja revealed that he had been given a secret assignment and was tasked with killing the enemy leader.  When the assassination had been carried out, he shape changed into the leader and we started to make our way out of the tower.  Unfortunately, he couldn’t bluff his way past the guards and their passwords, and we were attacked.  We fought out of the tower, but were soon overwhelmed by guards.  There was no way to escape the fortress completely.

In a desperate attempt to buy ourselves some time, we ran into the prison that had been built under the fortress in an old cave.  We had no chance to survive combat with the guards, so we decided to see what happened if we set the prisoners free.  As can be expected, they provided an excellent distraction.  The ninja and I sprinted to the docks used for the troop transport, sank all the boats, and swam to safety.

All in all, this was a favorite session for two reasons: one, we had some great action sequences and two, everything went wrong.  It is always great when a finely crafted plan works out exactly.  But when plans fail?  That’s when we get to make things up on the fly and hope for a lucky roll of the dice.  Gaming is all about using our imagination to come up with and describe tasks.  When plans fail for whatever reason, it forces us to think on the fly and make split-second decision.  To me, this is what makes gaming the most fun.  Both the players and the GM can get caught up in the excitement of what is happening and the game really comes alive for everyone at the table.  Picking one single favorite session is next to impossible because there are always great things happening.  But when, as a player or as a GM, I get to flex my creative muscles and make things up in the heat of the moment, I know that a favorite gaming moment is about to happen.



I whole-heartedly agree with Caleb when he said that it was  a great session because things went wrong. There is a fine line to be drawn by the DM to ensure that the PC’s don’t become discouraged because their well wrought plans fail over and over (usually this causes the PC’s to adopt the ‘screw-it, let’s just attack them’ mentality because they already believe taking time to craft a detailed plan would be a waste) and allowing the PC’s to win again and again just because they plan well.  Complications are the key. A minor complication could be having to bribe a guard who was supposed to be somewhere else. A major complication could be having to deal with the fact that your enemy is actually a polymorphed red dragon. And everything between.  Reward players for planning, but ensure that some measure of complications keep them on their toes and your sessions will become more memorable for it.


I’d like to thank @Caleb for his articles. Now that you’ve got a good idea of the type of games Caleb enjoys his next series of articles will be more in line with tips and techniques he uses to craft those same type of games for his players.


As always, comments are welcome.



Michael – AKA Mumbles


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    • Jonathon on August 10, 2013 at 12:48 am
    • Reply

    Another Wow!!!

    Very true that every gaming session has plenty of great moments in them; which definitely is a group effort. (See my comment in “My Favorite” part 2. By Caleb regarding video game 3d modeling.)

    Caleb’s story about the warlock and ninja drew me in and I could see everything happening.

    If Caleb writes this good on a blog, when are we going to be seeing a book by him on the shelf sitting next to Ed Greenwood, R. A. Salvatore, Monte Cook, and… errp… oh wait… I mean… When are we going to be seeing a book by Ed Greenwood, R. A. Salvatore, Monte Cook, and… on the self sitting next to Caleb.

    So is Caleb a player, a DM or both? Caleb wrote these blogs, what looks like through the eyes of a player; looks like Michael, at the end, implies that Caleb is a DM?

    What about a writer? Has Caleb written any adventures? If so, he should send one in for DnD Academy to post in the “Curriculum” -> “Modules” section.



    1. Jonthon,
      Caleb and I got to talking through Twitter after he had started listening to our shows. He asked if we would be interested in having a guest contributor to the site and I took him up on the offer. Right now we are playing together in a PbP game being ran through the Giant in the Playground forums, but otherwise we’ve never played together. As far as a book, I know he writes stories as well as articles. Perhaps we could convince him to let us post a short story or something some time. I’d be up for it. Might inspire me to do the same.


    • Caleb on August 12, 2013 at 9:40 pm
    • Reply

    Hello again…I guess it’s that time in the evening when I just reply everything at once.

    Yes, I have both played and ran countless gaming sessions. I wish I had more time to do both, but life does tend to get in the way.

    I am much more comfortable writing fiction than “adventures”. When it comes to games I create for a home-brew setting, I tend to write the story first, then convert it into encounters. But I do have several notebooks full of ideas that might one day make their way into adventures for this site. The format is not something I have much experience (as my gaming group has always run home-brews) but it’s something I can experiment with.

    As to fiction writing, well, who knows what you’ll see? I have so many ideas swarming in my head that I fear an explosion, from time to time, but there are some high fantasy nuggets buried among the horror and scifi that I tend to usually write. I am actually wrapping up some comic script proposals at the moment, but maybe I’ll dust off the old fantasy notes next and see what happens.

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