TTRPG Random Table: Downtime Conversation Starter

Just because your character has a +5 CHA bonus and advantage on every Persuasion check doesn't mean that you -- the player -- are capable of the same feat. Here are some conversation starters to get the ball rolling.

Sometimes you just need the right thing to spark some inspiration, and once the conversation starts it's much easier to keep it going.

Just because your character has a +5 CHA bonus and advantage on every Persuasion check doesn't mean that you do. As an introvert, sometimes it's hard to spark conversations even when you know your character would.

Sometimes you just need the right thing to spark some inspiration, and once the conversation starts it's much easier to keep it going.

There are four Broad topics, each with five sub-topics to help focus the conversation in a specific direction.

History, which relates to any character's backstory from before the adventure started. Where they've lived and why they're out in the world, as well as their friends, families, or enemies.
Connection, which relates to any two (or more) characters' connections with each other. Give a compliment (or, if you're the snooty type, ask for one!), hype up the team, let someone know they hurt you or that you hurt them. Or tell a deep secret, or bring up something you've noticed that you want your character to know about.
Feelings, which relates to how any character may be feeling right now. Is anyone anxious? Worried? Eager and ready? Stoic? Talk about it.
Goals, which relates to what is to come. There are four time frames cited here: next (maybe within a few in-game days), soon (within a few in-game weeks), far away (months away), far away (years perhaps), and end goal (when it's all over). There's also a starter related to the mission, which is vague on purpose. This could be their personal mission, the team's mission, or something else.

I would suggest rolling about twice on the table and combining the two results into a single starter, focused on yourself, another character, the party, or some combination.

Downtime Conversation Starter

d20	d100	Broad topic	In relation to...
1	1 - 5	History	Previous homes
2	6 - 10		Call to adventure
3	11 - 15		Friends
4	16 - 20		Family
5	21 - 25		Enemies
6	26 - 30	Connection	Compliment
7	31 - 35		Advice
8	36 - 40		Grievance
9	41 - 45		Secret
10	46 - 50		Inspiration
11	51 - 55	Feelings	Regrets
12	56 - 60		Hesitations
13	61 - 65		Excitement
14	66 - 70		Confidence
15	71 - 75		Indifference
16	76 - 80	Goals	What’s next?
17	81 - 85		What’s soon?
18	86 - 90		What’s far away?
19	91 - 95		What’s the end goal?
20	96 - 100		The mission

Examples

13,19 => Feelings (Excitement), Goals (End Goal)

"I can't wait to turn that murderer in. They've been going about unchecked for so long. Please tell me I'm not the only one!"

8, 17 => Connection (Grievance), Goals (What's soon)

"Look, I've been meaning to talk to you all about this. Are we sure this is the right thing to do? Maybe we have the facts wrong... Maybe... I dunno. I just don't feel right about this."