Getting Players To Do More With Their Free Time In Game . . . . Tips?

[TeiflingDM]

TL;DR Below

So just some information on our group.

We're a 5 player party. Me and my Brother switch off being in charge of the DM seat. (We both have separate "continents" that the players travel between) We both play DM/PC characters, and both tend to do bare minimum when in the DM seat, as to not "over glorify" our own characters.

The Party is made up of 2 sorceress, one wild magic and a dragon type (forget the exact name), a Moon Circle Druid, a fighter and a War Cleric.

Anyway, on to the topic at hand. I've noticed that some of the players treat gameplay almost like a video game. They just kind of go with the motions, and seem to be afraid to go "out of bounds" per say. For example, they travel between towns a lot, and upon getting to the town, or setting up camp, they all just find a tavern and sleep. Sometimes they shop, but don't really engage. They just ask prices and deduct gold, even if I try to RP with them a little bit.

I understand if they just want to get on with their current task at hand, but it leaves a lot to be desired from a DM standpoint, because I'd like to learn more about who their characters are, if that makes sense. I know what they have written on their character sheets, but I want to see them expand on those points.

I try to do things when I'm not in the DM seat to shake things up and show them that it's okay to do things unrelated to the task at hand, besides sleep and buy potions. For example, the last session we had, upon entering the town and heading to the inn, I asked around and found out if there was any news of sickness or injury in the village (I am the cleric, and proficient in Medicine). I spent that evening traveling through the village healing the sick. I'm also proficient with alchemy tools (player background stuff) so I try to tinker and craft potions and what not. When asked what everyone else was doing in town, they just said they were going to sleep.

They all seem stuck in their ways though. I try to give them "permission" to do other things, since they seem to stick to only the task at hand. Not sure if I'm doing something wrong, or if maybe their just dedicated to the cause. I try to be descriptive with locations, and have many premade NPCs to throw at them for flavor, but I rarely get to use any of them since they rarely engage.

I feel like a parent watching their child inside studying all summer. I just want them to go out and have fun. Maybe get into a little trouble from time to time. Make some new friends (or discover some new enemies).

I'm kind of rambling, so I apologize. Anybody have any tips or tricks? Something to get players interested in something besides fighting baddies and looting the dead. It would help me as a DM too, because if I knew more about what they actually enjoyed doing, I could think of some better stuff to throw at them in the future.

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TL;DR Players don't do anything in their free time between adventures. Frustrating as DM because I want them to develop their characters so I can write better content for them. Need tips to get them to engage outside of combat.



Thanks in advance. Sorry if this has been covered.

[Angelalex242]

Spread rumors of magic items that can only be discovered if they roleplay well.

"Ya know, rumor has it Bob never gets cold..."

(Cause he has boots of the winterlands...)

[DarkKnightJin]

Talk to the players out of game about it.
This isn't necessarily something that you can fix in-game, since it appears to be an out-of-game problem. The players aren't wanting to engage. Trying to entice the characters is nice and all, but if the players are not explicitly, out of game, told that it's not a videogame, and they can do other things than just go to the Inn and fastforward to the next morning to get on with the quest they're on.

[Pelle]

Make it interesting. Sounds like your players find it boring to smalltalk with the local baker about the prices of flour and so on. If they enjoy it, they will do it on their own, I don't think it helps to push them. If there is no conflict or interesting decisions to be made, spending game time on it feels like a waste. Just summarize the healing of sick people with a sentence, and make one roll for downtime activities like crafting. Weaving baskets is not "what the game is about" to the other players, so don't drag it out.


I find the players need some goals which make them more likely to interact with the setting. Either of their own or from their character, or because of working toward a long term goal. Maybe they want to spread theit faith, maybe they are looking for something, maybe they need local intel in their quest to stop the big tyrant. But you need buy in from the players, they have to be interested in exploring the world themselves. So talk to them about it, so you can find out if they are interested in it at all. Maybe they just want to be served a ready made quest and go slay some dragons.

[ImproperJustice]

Savage worlds has an “interlude” system where during significant portions of downtime players can draw a card, and are then encouraged to tell some back story about themselves based on the card drawn.

If it’s entertaining they earn a “bennie” which is the equivalent of an inspiration die.

You could adapt something similar and have it apply to types of NPC interactions or tasks and award inspiration die as an incentive.

[Unoriginal]

I agree with the people who say that this is an OOC problem that should be addressed by talking with your players about it.

Otherwise, have you looked at the downtime rules in the Xanathar's?

Maybe it'd give them some incentives to roleplay people.

Or maybe try to give them an adventure that requires interracting with more people, ex: "I want you to find X magic item that was stolen from my step-father, go talk to him for the details".

[Aett_Thorn]

From your description, it sounds like your players want their adventurers to be...well...adventurers. They like to go out on adventures, and other things in the world are just there for them to springboard from. It also sounds like they're waiting for you, the DM, to provide them something to do. That's not at all an unusual request for a game like this.

For things like this, it might be better to give them a few minor springboards for them to go off of. For example:

"You get to the next town a few days earlier than expected, and your contact doesn't seem to have shown up yet. What do your characters do in the meantime?" - Have some minor adventure points written up for various potential actions, including just staying at the inn (perhaps a fire breaks out in the town that they could have prevented if they had gotten out of the inn and talked to people, or something like that).

"You've planned the heist, but it will be several days before the (insert object name here) is in position. What do you do?" - The players might do something stupid and get arrested, meaning that they need to break that character out in another little mini-heist.

"You've been sitting in the inn all day waiting, you can hear a ruckus outside that seems to be building."

"You slept for two days at the inn. When you come out, you find the rest of the townspeople dead of some mysterious illness. The people within the inn don't seem phased by this."

I'm not saying that you need to do that every time, but doing it on occasion might get them out a bit more. Still, your players might not want to roleplay that kind of minor stuff. They're there for high fantasy and Dungeons & Dragons, not "Adventurers & Dayjobs".

[TeiflingDM]

I don't necessarily want them to haggle prices on their goods or small talk. And maybe I'm expecting too much of new players. I just think they would have more fun if they let loose a little more in game. It feels like the only thing they actually do or say in game is "I want to make a X check" and then "Okay I inform the group, now what?". Like I know that they're all gold hungry. Maybe I have to start enticing them more with little mini quests to earn money or something. Will definitely speak to everybody outside of the game.

[Unoriginal]

Like I know that they're all gold hungry. Maybe I have to start enticing them more with little mini quests to earn money or something.

Well yes, it's a method. Starting the next quest by having someone come tell them to meet with a rich person who want to hire them could work, too.

[Vogie]

If they're focused and quest-driven, take a card from MMORPGs and give them little quests that have no impact on the overall storyline, and maybe open up NPCs to meet, various reputations gained or lost, or just a way to make money

A savvy merchant calls to the party as they're walking by, insinuating that they need better shoes, and can mention that they could craft some shoes that are completely silent, if only they could get some hands on moonsilk.
There's a bank robbery, or bandits attack the town in general.
Go hunting the wolves that are attacking the sheep of John Peters (you know, the farmer?).
Because of the changes during the war, there's a travelling troupe that provides healing and will teach others how to use healer's kits.

[DMThac0]

I have had an on going problem with the same thing, how do you make downtime, or long travels distances interesting without rolling a d12 and throwing random monsters at them to pass the time. I have not found a perfect answer yet, and I'm 2 years into the game now lol.

A lot of the previous posts pointed out having the NPCs initiate some sort of conversation/plot hook. This is rather helpful, you can have your players running around the whole town talking to various people to gather information, tools, quest items, etc. It will also give you a chance to flex your improv powers, and through the NPCs you can start pulling the character's stories out of them by asking questions.

"I've never seen a lass with horns on her head before, did you have an accident with a spell or something?" I had an acolyte wizard ask that of a Tiefling in my group. It helped reinforce that Tieflings were a rare thing in the world, it showed that there was an inherent lack of knowledge about the race, and it gave her a chance to talk about what she was.

Sometimes you can inject the backstory your characters have given you into an event, causing it to become a piece of the action. The Sorcerer in my group had his shirt torn by a weapon attack in a fight, it showed the draconic scales from his arcane lineage. The NPCs who were present all gawked at him, mid combat mind you, as something like this was odd. His background said something about him being ashamed and embarrassed by those scales.

If you want to have your players open up, give them the tools. Some of them will take the reigns and run when they see they have the freedom, some will just sit there and stare at their cell phone until you ask them to roll initiative. Don't stress it too much, learn your players and cater your narrative to show them what they can do, reward them by playing along when they do step out of their comfort zones.

[HolyAvenger7]

Had a similar problem in our game with newbies that only wanted to fight rather than role play. DM solved it (somewhat) by forcing a few encounters where fighting wasn't an option so we had to role play our way out of the situations and then rewarding us with a small token of loot. So, to echo the above, there would be two factors.
1. No other option but to role play (Be it time, needed information, need to earn money, OP opponent...)
2. Reward for role playing well. (It could be a trinket, or verbal praise and finally moving on to some adventuring)

[Armored Walrus]

I think many GMs struggle with this. It's only partially on the players. D&D itself puts the majority of its resources into the combat pillar of the game, and I think most DMs spend most of their prep time on the combat portions. It's also the part of the game that tends to take up the most time - half an hour to an hour goes by in real time in order to resolve 60 seconds of combat - and then the fast-forward button gets pushed and we skip to the next combat.

Two times in my campaign where I was able to get my players out of tactical rpg mode and into story mode stand out to me:

When my campaign launched the party members each had a task for which they had to travel about a week from the capital city in order to accomplish. Some of them shared the same task, some were totally unrelated. None of these quests were "kill quests." One was to pick up some mysterious spell components for a patron, one was to discover why she hadn't heard from her pen pal lately, one was simply to escort the group and get them safely where they needed to go. The travel there I think was pretty typical - some days of just moving forward that were narrated in seconds, a couple non-combat obstacles - a narrow trail over a cliff that threatened to crumble under them, a large chasm in their way that they had to figure out how to cross - and a good handful of wandering combat encounters. Once they got to town, though, there was nothing to fight. The ones that were there to pick up the spell components had to meet with their contact, the other had to head to her pen pal's home, etc. When they tried to pick up the components, they discovered their contact had already given them to someone else; someone who had given the correct signals, so they did some investigating to figure out who the person was, whether anyone in the area had seen them, etc. The one looking for her penpal found the place deserted, some prominent items missing, and a curious neighbor who was able to converse with them and give them info regarding the last time the person had been around. That session didn't involve any combat, but every player was fully engaged for the whole session.

The second time I had a non-combat piece of my session that I thought went exceptionally well was when I stole AngryGM's chase scene (http://theangrygm.com/how-to-build-awesome-encounters/) whole cloth and dropped it into my game.

There certainly have been other times that they've engaged, but those two stand out to me as the sessions that broke them out of game mode for the first times and showed them there was more to do in this world than just find stuff to kill and take its stuff. The key, I've learned, is to give them something they want to engage with. If you're spending the majority of your prep time on combat encounter building, your players will likely spend the majority of their time in combat, but if you spend some time putting together different challenges and obstacles, they'll engage with those. Well, some of them, and some of it will just not get used. Fortunately, it's easy to re-purpose stuff that doesn't get used in one session, and reintroduce it as something completely different in a later session.

If you want one fool-proof, quick and easy way to convince your players they should be interacting more with your world, have an NPC try to get their attention, and then if they fail to engage, have that failure to engage cause them some problem down the road. "Oh, you didn't get your anti-vampire charm from the local priest? I'll enjoy feasting on your blood tonight." etc.

[TeiflingDM]

Good advice all around. Thanks to everyone for the input.

I'll try to talk to my players out of game, but before that I think I want to try for a few more games with trying to teach them without directly explaining things to them. Don't want them to feel like I'm trying to force them into RPing either.(Plus I want to see if I can do it by example only, lol)

[Derpy]

I've been DM (or GM or whatever they call it nowadays) for a little more then 3 years now. I've been playing maybe twice that, and interested in the game for 15 years (read the books, but no groups in my area). I've had led campaigns (once a week, every week), both a year and a half, though the second one is ongoing. In both of them I told the players beforehand that I would be trying to get a nice mix of combat and social interaction. It put both them and me in the right frame of mind.

First off, are the players expecting role play in addition to/with fighting? If they signed up for kill and loot or with the expectation of just that, then no amount of coaxing or gentle hints will be likely to get them into town for a good time; the good time is the roll of the dice, the cracking of heads, and the looting thereof. Second; are they roll playing while they go though encounters or are they acting with just mechanics in mind, if they aren't into their characters in combat or an exciting situation it is not likely they will when they are in a sedate situation. Thirdly, are/were you giving them options and opportunities; if you shot them down once or twice early on it could have affected their desire to flex their roles.

I had a three step plan to get the party in the right frame of mind for roleplay. First, before the campaign even began I set the stage for the party, I laid out a brief of how the world was, why the party was where they were, and asked the party to do the same with their characters; a background beyond the cut and paste provided in the books, I also wanted one real fear from each of them (something I could add to encounters later [sparingly] to spice it up; it didn't need to shut the character down, and I didn't want it to, but maybe provoke an Indian Jones like response [snakes, why'd it have to be snakes!] that bought them a bit of life). I was pleasantly surprised by the work they put into their characters.

The next step was taking their backgrounds and putting them into the world. I could have a party wandering with no connection to the land, but if they don't care about anything in town then they wont have fun interacting in that town. They enjoyed the times they would wander into a new town and an NPC would see them and go... “Player! It's been years since I last saw you, what's been going on? Remember that time... [insert something from their backstory a bit expanded on].” It showed I cared enough to put their work into the world, and something the player is involved or invested in is a much greater hook; as a rule people tend to be invested in themselves. The party in my campaign has chosen a town to be their base based on the NPCs in that town, bought property in the area, and give away some loot to their NPC friends and contacts (nothing rare or magical, but their altruism caught me off guard).

The final step a two parter; brushing up on my notes and improv skills AND throwing in a few token RP elements to every town. I can't have a dialog tree for every NPC; there are too many NPCs and the players are too varied in the actions they can take, and if every NPC was like me there would be no incentive to spend time with more people in town (I'm not flattering myself about my own social characteristics IRL); they would all be the same. It's been difficult, I'm hardly an actor, but some NPCs like the party, some don't care, some frown on their freewheeling adventurer lifestyle. Happy, sad, depressed, insane, dutiful, deceitful, trope, stereotype, and unique; every Tom, **** [Richard], and Harry makes Ferbrzu the Left Handed seem more... well, more. Having a list of NPCs of note in town, even if it's just a name, a trait, and an occupation gives me a base, and improv is forced to carry the rest. As the party interacts with an NPC I add more (caught player shopplifting, offers good deals on Friday, has an obsession about the color green, hit on, was hit upon by..., whatever). The token RP elements are fun things I add to every town. The party walks into the baker's (everyone has to eat or supply or whatever), and they see a gnome with dark green spiked hair and thick glasses laughing triumphantly; he runs up to the party and thrusts a roll at the one in the lead and goes “eat it! Eatiteatiteatit! Its my life's WORK!” it's something that should be normal, a baker, with a subverted expectation; the gnome is crazy, like a mad scientist. They're forced to react. The one in the lead (whoever had wanted to walk in there, not important really) took a nibble. Turned out to be a cheddar and herb biscuit (you take a small nibble, the warm bread has a savory and rich taste and seems to melt in your mouth in gooey goodness) the gnome had been perfecting... and the NPC hung on every word the character had to say about it, before going on a short insane gnome rant about his work and selling them some foodstuff. They came back for new experiments several times just have a crazy gnome make things for them to eat.

As a final thought; there are many ways to try to get players invested in the world. I went with the world itself being the reward. Finding that odd person, getting a funny encounter, getting a dramatic encounter, learning about the odd person in the town, talking to the shop keeper. Not everyone plays the game for this kind of thing and I feel like the players I've DM'd for have been good to me as I hope I've been to them, but some people are going to want to skill check everything, some people are only going to be interested if there is a financial payoff for them, some people are just looking to dump loot and get back into the fight; talk it out with the players and (if they are interested for whatever reason) put the same effort into town as into a dungeon or encounter, let them know, and tease it out; lead a bit until everyone gets comfortable with their roleplay. At the end of the day it's whatever is fun, if your players remember the time a warlock eldrich bast kited a giant around with 10' pushbacks or the time the party got piss drunk and made up a song on the spot on the local tavern table about their everlasting love for a woman who's name they got confused with her sister.

[Contrast]

Give them missions with an open ended goal without an obvious solution. The more they get used to wandering around and asking random NPCs for help/advice, the more second nature it will become.

Have unrelated events going on. They happen to come to town while a festivals on. There's a darts competition at the pub they're staying in. Someone yells thief as a young man runs past the party. Doesn't have to be anything major, just something to fire the imagination/break them out of the rut/comfort zone.

That said, it may just be that isn't what your party thinks is fun. Dangle the threads and let them choose if they want to bite.

[GlenSmash!]

"I want to make a X check" and then "Okay I inform the group, now what?".

This is something that could be improved upon for sure.

In 5e players shouldn't be asking to make checks, they should be describing what the characters are doing in the scenario and the DM decides if a check is called for.

If my player asks to make a check, I'll in turn ask them what they are actually doing to try and figure it out.

At first it frustrated my players who thought that you were just supposed to roll dice to try and do stuff. But after a while they really liked that sometimes their approach would succeed without rolling, or they'd have advantage based on the approach they took.

[Xetheral]

I recommend giving the party loot that they will need to show initiative to be able to exploit. Examples include:

Rare art by an obscure artist that the party identifies as incredibly valuable, but most merchants won't know that. To sell the art they'll need to track down an art dealer or a connoisseur. A rare ore in refined (but unworked) form suitable for making a powerful weapon, but only if they find a exceptionally skilled smith. A broken magic item only repairable by a specialist. Secret information that is undoubtedly valuable, but only if they can find an interested buyer. An ownership stake in a struggling enterprise. It's not worth much unless the party takes the initiative to help make sure it stays profitable. A new spell that isn't very useful for adventuring (e.g. Relieve Drought, Tuckpoint Wall, Soothe Toothache) but that would be worth a fortune to the right spellcaster.

[quinron]

The most effective way I've found to get players "in character," so to speak, is to make their characters' motivations important to the aspects of the game that they're most interested in. Since my current players are big on combat and dungeon-crawling, I've started putting multiple monster groups in most of my dungeons and giving them humanizing things to do, like playing cards or sitting around griping about their bosses. Depending on the order they encounter the different factions and how the PCs' interactions with them go, certain groups might be convinced to become allies or might get offended and become hostile toward the PCs. I do about twice as much character personality planning for a simple dungeon as for a town, because that's where that work is going to pay off.

[Armored Walrus]

The most effective way I've found to get players "in character," so to speak, is to make their characters' motivations important to the aspects of the game that they're most interested in. Since my current players are big on combat and dungeon-crawling, I've started putting multiple monster groups in most of my dungeons and giving them humanizing things to do, like playing cards or sitting around griping about their bosses. Depending on the order they encounter the different factions and how the PCs' interactions with them go, certain groups might be convinced to become allies or might get offended and become hostile toward the PCs. I do about twice as much character personality planning for a simple dungeon as for a town, because that's where that work is going to pay off.

This is a very interesting take on this, and I like it, and will steal it. It's the difference between just cooking the meal and wondering why no one is eating it, and actually dishing it up and setting it out on the table. "If the players won't come to the social interactions, I will bring the social interactions to the players."

[opaopajr]

The correct answer is having a mature talk with them about your table expectations. Something like: "This is not a video game. This is a feature, not a bug. If you want a video game, go play one. XOXO kthxbai!" :smalltongue:

However reorganizing incentives openly works, too. Increase XP for Explore & Social Pillars, Decrease XP for Combat Pillar, and make Adventures more than Kill Quests & Fetch Quests. Add factions between allies & enemies, play with ambiguity, add in restrictions through expectations, custom, & law...

Reaching 1st lvl to 20th lvl, or any other video game-like achievement, isn't that meaningful of a goal because any GM can readily hand any of these goals to you on a platter. It's all imagination on the honor system, so the bragging right are puny. The point of an RPG is enjoying, and engaging with, the creative mind behind the campaign 'dish' placed before you at the table. If that is beyond what they can conceive of enjoying, that's OK, not everyone can share in the same types of fun. :smallsmile:

[Vorpal Crowbar]

Ask them to create a character goal - Something Grand - Some that would take time to achieve - The plots start to write themselves if the goal is big enough.

Aspire to Become a mayor, a king, a God, or to unite the world in harmony, or bend it to your will, to start a war between rival countries and to conquer both of them. Dream big - It's all possible.

My characters side project in one game - Is the goal of bring joy to the joyless citizen of the Underdark.

In another - It's world domination. At level 7:

I've already made alliance with Khans, Demons, witches, God Emperors, Demi-Gods, and Mothra,
Travel to and caused havoc on 3 different planes,
Started a revolution in a city-state and become the leader,
Ruined the economics of the Four largest Countries in the world
And remade alliances with some of them I destroyed.
Now, I'm fortifying and terraforming my city-state for economic supremacy.


Just go do it, because, why not.

VC

[ad_hoc]

Would you watch an action movie about characters between the action?

Downtime is best handled off screen. Character building happens on screen. If it isn't relevant in the adventure then it doesn't exist.

The downtime rules in XGtE are good for adjudicating off screen time.

[Contrast]

Would you watch an action movie about characters between the action?

This analogy is falls a bit flat because yes, many people do indeed find a narrative more satisfying when the details of a movies character are more fleshed out and well established.

An action movie is more like a one-shot. You're here to get to the meat, no time for dilly dallying.

A campaign is a more like a tv series. You could just do constant action but that is going start to get a bit boring for many people after a few episodes.

[Chugger]

Tavern hijinx can get...boring - yeah, very boring. Or can be hysterical.

If you must force them to roleplay, set the adventure in a tavern. If they don't find person x, sweet-talk person y, or end a tavern brawl - or do something in the tavern - or things in the tavern - the adventure doesn't progress.

[Belier]

To me it sounds like your players want to play a railroad game and have satisfaction completing the quest at hand like you would do on a video game as you state.

I can understand your point. Last night I was playing a Druid and in the tales trees tell advanturer league a villager come back to town almost dead with both eyes replaces by stones and a stab in thr chest and written message on him. I decided I'd stay with him as I am a eldath druid neutral good and stayed the night taking care lf every of his needs. Even using druidcraft to make good smells to ease him on his bed. I was looked at are you really gonna leave the quest to take care of him? Hell yes I am lol. Then the dm and player wanted to put me on railroad and he said you estimate the guy will be fine in 5 day of bed rest and you took good care of him and the players went back for me lol

[Lord8Ball]

What I would recommend is that you allow your players to choose three goals for their character at the start of a session. Completing these goals may grant experience based on the difficulty of the goal at the time of completion or a reduced amount if the player is working towards it. If you use this method I'd recommend removing experience for just killing monsters. From there I'd probably add things like lifestyle expenses, paying gold and downtime to train for level ups, and overall encourage them to roleplay. Remember to ask your players how they would like to do their actions and their characters thought processes based on the situation.

[Requilac]

I don't necessarily think your players are so much afraid of roleplaying small details as they are just not interested. There are many different play styles in D&D and many people have different preferences. Perhaps they just don't care about those small character aspects and want to get into the action. Many people like that, as evidenced by the amount of action movies and video games exist out there. I as a DM ran into a very similar problem to you and just wished my players would do a little more RPing, but eventually I just learned to accept that they aren't interested and I think all my games have greatly improved since then. Talk to them out of character about this. If they really do admit to be afraid of roleplaying, then assure them that you will support it and create incentives. If they claim to just not care, just go with it. I can say that as a DM sometimes what is best for the table is not necessarily what you would like to see, and this is a case of that.

[strangebloke]

This is something that could be improved upon for sure.

Yeah. You stole my line.

You call for checks based on what they say they want to do.

Also: don't give them open-ended downtime. DND is about decisions. Give them decisions. Xgte downtime rules are great for this. The PC is a criminal? RP an old criminal acquaintance blowing into town, asking him if he wants in on a job. Guy's got proficiency with an herbalism kit? Have the local apothecary spy the kit peaking out of his pack and ask if the PC is looking for a job. Have the bar tender note that if you're good at fighting there's good money to be made fighting in the pits.

Eventually they'll get the idea.

[Asmotherion]

Include Dawntime. Explain it in the form of Narative Dawntime:

"The following week, was relatively calm for this town.
At this point, if you want to do something specific during that time, you can start describing your attempts to me"

If you go at it in a Real Time perspective, most players will get lost, and won't know were to start what they want to do.

If the party breaks up for a wile, especially a large party, the best way to handle it is trying to deal with it as a chain of events, and breaking the chain if something in the chain does not trigger.

Give a higher priority of resolution to the easyest chain of events (one that has the easyest DC, allows retries, and generally will go as planed), and the lowest to the one that will need the most adjusting (the one that will include the most failures due to high DCs, does not allow retryes, and may have the player end up somewere where he didn't plan at all pefore Dawntime began.

It's like the Player having a Short term Plan, and if everything goes according to it, Dawntime is presumed to go as planed.

[RazorChain]

As a DM you should engage your players and their characters. If they arent proactive then you should be. Roleplay the innkeep, describe the inn, village or whatever. Have people ask them news, invite them to gamble, tell them rumours.

Make adventures where they use their talky skills, inquire about rumours, buy people drinks to loosen their tongues.

[Avonar]

Something I found that works was just telling players there was going to be downtime. We started a new campaign where I wanted downtime to be a thing, telling players beforehand allowed for them to come up with goals for them to achieve for it. One guy is using his downtime to learn to read, another is looking after some orphans. Just tell them they should come up with something their character would like to do during downtime.