5 Monstrous Duos for your Next D&D 5e Session


So many things, no matter how great, are boring by themselves after a while. You might think that a Slaad is the best monster this side of the Monster Manual, but if you use it in a predictable way over and over again, you and your players will get bored.

Great things usually come in pairs in roleplaying games: orcs and goblins, zombies and skeletons, dungeons and dragons, the tarrasque and the twitch in your DM’s eye that says you really pushed them over the edge this time.

So, how better to keep encounters fresh than with fun pairings of monsters that break them out of the ordinary and make the encounter worth remembering? I break down 5 great monstrous duos to use in your next 5th edition D&D session. Some of these use interesting mechanics specific to the two monsters, while a few are cool encounter ideas in which the monsters presented fit nicely, though they may be swapped with others.

The roper and darkmantle combo is nothing new, but it is oh so great. It’s even better when the roper is a stalactite like the darkmantles rather than a stalagmite. Everything going black as teeth gnaw at your skull, the feeling of constriction around your body rendering you struggling to get free- as you feel yourself pulled off the ground, higher and higher.

I personally prefer the ceiling variety because it’s another obstacle to overcome. Want to cut off the roper’s tentacles? You’re looking at some fall damage for the grabbed character. Want to damage the body of the rocky monster? You’ll be impeded if you’re primarily melee and don’t get creative with your actions.

This duo (or group if you choose to use multiple darkmantles) are a remarkable surprise encounter for how quickly they can throw your players into disarray- and hopefully, force them to come up with a viable strategy on the fly that deviates from the same hack-slash-spell strategies they employ. This encounter is also easily scalable- from the number of tentacles the roper has, to the damage it does, to how high on the ceiling it is or if it’s on the ground. Just make sure you don’t completely nullify your melee combatants, otherwise it won’t feel like something they can actually overcome.

Banshee/Will O’ Wisp
This is a low level but easily fatal combination. I came across it accidentally while preparing a crypt adventure, and I ultimately couldn’t bring myself to insert it against the poor, unsuspecting players. It’s two fairly low DC checks to instant death, but in a group of 4 or more the chances of a character going out this way is surprisingly high.

It starts with the banshee’s Wail ability, which can be used once per day. All creatures besides constructs and undead must make a DC 13 Con save, taking 3d6 psychic damage if they succeed- and dropping right down to 0 if they fail. I can count on my party all having at least a +1 to their roll here, but that’s over 50% fail rate for them. If they can pass, they’re safe provided the 3d6 psychic didn’t take them down, though they will all be wounded. The real pain comes in the form of a will-o’-wisp or two. Their consume life ability allows them to, as a bonus action, force a creature at 0 hit points within 5 feet of it to make another constitution saving throw. This time it’s only a DC 10, but unlike Wail this can be used as a bonus action every turn. Oh, and if the player fails, they die. Outright. Just like that.

For a CR 4 and CR 2 monster combination, that sounds brutal. In theory, with bad enough rolls a high level character could be instantly killed by this. Seriously, I had to show some restraint to not throw this at my party of six. But, next time their heads get a bit too big, maybe they’ll have an encounter with this pairing.

Hear me out on this one, as I pulled this off in Knights of the Pool Table to the delight/bane of my players. Kobolds working for dragons is as old as Dungeons & Dragons itself, but it’s all about how they work together.

Kobolds are devious little cretins and dragons are intelligent masters. You can’t change a kobold’s stats (well… you can), but you can change how it behaves. The Monster Manual lists the kobold as using a spear and a sling. What kind of dragon is going to be thinking: “My worshippers are throwing rocks at people and missing most of the time. That seems like a sound defensive strategy.”? The answer is none. But rarely do I see people re-outfit a creature en masse. A leader in a group? Yeah, maybe they have a damage die higher of damage from trading from a shortsword to a longsword, but to take an entire group and really amp up the damage is not something we see often enough. So, fix this and have your dragon outfit them with crossbows, light or heavy. Turn that d4 of damage into a d10 and really amp up the danger of them.

Have the dragon organize them and deploy good tactics, such as having high posts from which to shoot down from, or hidden compartments from which to flank from. You don’t need to go full Tucker’s Kobolds on your party, but you should elevate them from the 1-hit minions that they are. And, when you’re dealing with dragon intelligence, you can use the full range of your own mind to foil your players. The reason that this worked for me as a DM is I was able to introduce these smarter kobolds before the dragon was to be fought. En route, the group encountered kobolds with crossbows over a turn’s movement away, above them on the ledge of the road that ascends the mountain. They made a comment about the encounter being tough for being just kobolds, and as they encountered more and more they had to start stealthing. Finally, they scoped out the dragon’s lair and *gasp* formulated a plan instead of just rushing in. They saw the perched kobolds, they saw the dragon, and they knew they couldn’t just ignore the former while they got filled up with crossbow bolts. It was a fun battle, with half the party dealing with crossbow bolts while the other tried to avoid being burned to a crisp.

As a bonus, 5e has flying winged kobolds, also called urds, that usually drop rocks. Load them up with crossbows and watch as your melee characters throw their swords up in frustration. Or give them heavy crossbows with funny blowback effects, if you’re into adding some comedy to your session.

Kenku/Invisible Stalker
I’m going to tell you why this is a great combination. It has more to do with the story ramifications than the actual encounter itself, though it is a fun encounter, too.

An assassin’s guild with the PCs as the target. A not-so-charismatic wizard who needs to have a “chat” with the players. The BBEG is trying to take the characters hostage. All possible reasons for this pairing, with either half being good at taking direction and fulfilling. The actual mechanic here, of course, is to lure the players in with the kenku and spring the invisible stalker on them. Maybe even a band of kenku or other ruffians could join the fray from hiding spots once the stalker makes the first move, and the kenkus’ ambusher ability to gain advantage when they have surprise can make for a damaging first round of combat.

Again, I like throwing players for a loop, but giving them a fair shot. This is a perfect encounter to introduce them to the vile King of Thieves they’ve heard so much about, or maybe just a really rough part of town. Throwing them off their feet but being prepared for the rebound is key, and this encounter can end in a lot of ways that aren’t bloodshed.

Purple Worm/Piercer
Ok, this one is a little bit more out there. I see a very cinematic scene playing out. Your players, deep in a cavern. They’re battered, tired, and worn from their hard fought battles against whatever it is they needed to kill in here. A rumbling. Louder. Closer. Finally, a purple worm bursts through, chase scene ensuing. Ideally, your party should be too low level or beaten down enough to not want to face this beast. Do anything you can to make them run away- because that’s where the fun starts.

One mechanic that worked in many different video games is needed to look out for things falling from the sky. No one ever said those things couldn’t be living creatures who have the life purpose of falling just so they can try and kill you. Make the first few piercers a surprise as your group tries to outrun the worm, but then I would suggest mixing up the mechanics. Firstly, you should figure out a way to do the chase scene that works for your group beyond standard initiative and actions. This can be anything you want it to be, and worst comes to worst standard gameplay if fair. Regardless, I do think you should change the piercers attack to a saving throw. It only has a +3 to hit, so it shouldn’t be that high; DC 10 to 12 at most. This will allow you to try and keep up the pace of the looming danger from behind and above, while the players get to nervously roll their dice over and over, waiting for escape. The worm here should deploy some form of tactic here and there other than chase- maybe it decides to go the other way of the players in a tunnel, only to come back and chase them in the opposite direction, now forcing them to deal with the inevitable difficult terrain.

I like the idea more than the mechanical aspects of running a combat like this, and I’m sure all you creative DMs out there can find a way to make it a truly remarkable encounter.

That’s all for today’s article! Which of these combos should your players be wary of next session? Do you have any great monstrous duos? Let us know in the comments or on social media! Speaking of which, be sure to check out our dice giveaway on Twitter, follow us on Facebook, and check out our social media elsewhere.


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