20 Questions to Build Bonds in an Adventuring Party
I am about to start several new campaigns, and it has me thinking about the bonds between characters. While many adventures begin with the party not knowing each other, and being united by a common goal in the first few adventures, you can also start out a new campaign with the player characters already knowing each other.
Of course, just because you say the party has been traveling together for a while doesn’t mean that the players will feel that way. The players will still act unsure of the others and get the other characters' names wrong so many times that eventually the player will just rename their character to the new name. Sorry, Aisling, I promise to get your name right next time.
To help the party get past those first few session jitters and already invested in each other’s characters, here are 20 questions that you can pull from! Each player shouldn’t answer every single question; you can have them roll or pick up to 3 or 4 questions.
These questions are also great to bring out during short/long rests for established parties when you want them to grow tighter together.
20 Bonding Questions
Each of these questions is open-ended, and there are no gotchas. This is simply to help players not only flesh out their own character, but the adventuring party as a whole. As a general rule, if a player makes up lore about another player’s character, that lore doesn’t have to be real. That can be what that character thinks of the other.
Ultimately, this should be a back-and-forth conversation between the two players and is about connecting their characters deeper. No one should force their ideas on another or have control over another player’s character.
Lastly, these questions should be spread out around the table. A single character should not have more bonds than other characters.
Examples for each question are provided in italicized text.
1) Your character met one of the other characters several years back, but you aren’t sure that they would remember you. What was this event, and why is it that you remember the character?
I was a server at a tavern that the other character was passing through. They were on an adventure, and I listened to one of their stories about fighting a kobold off with only a shield and a broken spear.
2) You heard a rumor about another character. Was this a good or bad rumor? Does it color your opinion about them?
The rumor I heard was that they had a family back home that they could never see again. They had gotten in trouble with the local lord, and they feared for their family’s safety if they stayed.
3) Your parents were friends with another character’s parents. What happened to the relationship? Has it affected your relationship with the other character?
Our parents lived in the same village. While mine died when I was young, the other character’s parents took me in and raised me like family. I always wondered if the other character resented me for taking some of their parent’s attention away from them.
4) You once had to share a room in a tavern with another character when you were strangers. Would you ever do it again? Did the other character snore?
There is no dragon hoard great enough to share a room with that character. They sleep talked the entire night about how they were going to conquer the world and enslave it to their will. I wished they had been snoring.
5) You covet an item on another player’s character. What is this item? (The GM might allow the other player character to gain a slightly magical trinket or a common magic item.)
Their helm is incredibly cool. Their eyes glow with the red and orange of hellfire. I saw them use to scare off some bandits and I’ve wanted it ever since.
6) You once followed another player’s character when they didn’t realize it, and you witnessed them meeting someone. Who did they meet and what was the meeting about? Are you worried about the meeting?
When I followed the character, I was worried as they seemed extremely nervous. I wanted to help if I could, and I saw them meet with some roguish sort. They passed a few coins to the rogues who disappeared. I’m a bit worried if they were paying off a debt or, more concerningly, hiring them to do something terrible.
7) You and another player’s character had an incredible quest. What was the quest, and how did the other player’s character save your life?
We had to fight our way into a cave where a horde of kobolds had gathered. The cave was dark and the kobolds were using hit and run tactics, but luckily the other character seemed to have a sixth sense of when they would pop up and we easily cleared out the cave.
8) You lost a bet to another player’s character, and now you owe them a favor. What was the bet about? What is the favor you owe them? Do you think they’ll ever call in that favor?
If they ever call in the favor, I’ll never live it down. I was starving in the forest and stumbled on their campfire. I asked for a game of chance; if I won, I’d get some of their rabbit cooking on the fire. If I lost, I’d be their valet for a week. I lost. Twice. They did feed me at least. Now I’m just waiting for them to call up that favor…
9) You and another player’s character have a small rivalry going on. What is the rivalry about? Are you worried that you’ll lose?
They said they could kill more orcs than me; and whoever has the most kills doesn’t have to pay for drinks. I’m at 3, and they’re at 4. Luckily, there is an orc war party nearby, and I can’t wait to have them buy me the finest elven wine this rundown tavern has.
10) When you first met another player’s character, they said something really odd to you that has stuck with you. What did they say? Why did it stick with you?
The first words they ever told me were that my parents were proud of the choices I had made. I never knew my parents.
11) Which player character do you see the most of yourself in? What about the least?
The cleric is a wise and courageous individual; I hope to one day have that same steadfastness. The bard, on the other hand, always seems to have a reason to flee a battle.
12) What stood out to you first when you first saw the other player’s character? Was it a wrong first impression?
I didn’t know they made swords that big. Or muscles that big. Or that skulls were such a huge fashion statement. Its very weird on the most empathetic and kind being I’ve ever met.
13) Has the other player’s character ever talked about their home? Does it feel like home to you?
The dwarf once told me about the city they came from. It was a city built inside of a hollowed out mountain. It sounded fantastic and wonderful, and way too strange for me to ever want to live out my life there. You’d never see the sun and I’d always be thinking about avalanches.
14) If your adventuring party had a name, what name would it be, and would the other player characters agree with your name?
The Vivacious Purple Rats is an incredible name, and I’m going to make sure all the bards in the worlds know it, no matter what everyone else says.
15) Another player’s character had an unusual pet. What was it? Would you want one?
Apparently owlbears make good pets, so long as you train them from a cub. I’d love a little owlbear as my best friend, but I’d be worried about it surviving an adventurer’s life.
16) You saw another player’s character in a dream, but you are pretty sure they had the same dream as you. What was the dream about? Did you two have this dream before you met? If you had it after, did it push you apart or pull you together?
About a year before we met up, I met this strange person in my dream. They said we were destined for greatness. When we met in person, I tried asking around the topic, but they didn’t seem to ever recognize me. I’ve decided to stick around with them to see if anything comes of it.
17) You had to tell another player’s character ‘no’ once. They took it badly. What was the triggering incident?
Apparently you should never stop the raging barbarian from killing every single goblin they come across. Something about family, goblins, and slaughter. Now I just make sure to stay far away from them if I even catch the whiff of goblin.
18) What is something you are scared to tell the other player’s character? Is it something serious, awkward, or nonsensical?
I’m not saying it makes sense, but my character is scared to tell the other character that they think their armor choice is rather… dorky. A full metal helmet, armor wrapped around their chest, arms, legs, and even their hands and feet. It’s like they’re scared of getting hurt or something.
19) You once saw the other player’s character dancing to a terrible song played by maybe the worst bard you have ever heard of. What was the song about? Were they a good dancer?
I don’t recall the name of the song, but it was a song commissioned by a noble a hundred years back about how you should never betray them or you’ll have your head on a pike. Their dance moves were a lot more violent than I thought dance moves could be.
20) The other player’s character knows something incredibly embarrassing about you, and you haven’t worked up the nerve to talk to them about it. What is it that you are embarrassed about?
I once had to pee so bad while we were in a dungeon that I peed in my full plate armor. I thought no one noticed, but the other character made several overt comments about having to pee while we were leaving and maintained eye contact with me.
Do you have any questions you like to ask to help characters bond more? Share your favorites in the comments!
Like what we do?
Join our Patreon!
You’ll get early access to deep dives, the Homebrew Hoard
featuring 500+ monsters, ad-free articles, and more!
Follow us on Reddit to keep up to date on everything we talk about!
