The Jovian said:
Welcome to the hobby! Let's take care of the big problem I can see in your post.
I'm currently in the process of planning out the next adventure in the campaign which is pirate-themed high seas adventure, involving a party member being kidnapped by pirates and the rest of the party going on a rescue mission across the seven seas.
So Braddock the Fighter gets kidnapped, his party goes to rescue him... What is Braddock doing? Is he supposed to sit around in the brig off-screen while the rest of the table has fun chasing him? Is he going to get some stimulating conversation with his jailer about the ethics of piracy while the other players get to sail through storms, wrestle sea serpents and buckle some swashes? What if the character tries to break out? Are you going to slap them down with overwhelming numbers of pirates and throw them back into their cell? What if they try to fight to the death just so they have something exciting happen to them?
The captured friend is a strong traditional story hook, but it doesn't work particularly well in tabletop games because the climax of the story is the rescue, meaning that the player of the captured character has to spend 2-4 hours waiting for that moment (if things get wrapped up in one session). It's compounded by your choice of game and genre: D&D is a party-based combat-oriented game, meaning that an isolated character faces a much more difficult challenge than you might first think, as they have a narrow range of skills and a specific role during fights. As well, the party will have troubles of their own compensating for the missing person- they're already short-handed with 3 characters, taking one of those away pushes them into the "inadequate" category. In a similar vein, a 'high seas adventure' implies big setpieces and overblown character moments, which is a lot of fun. However, the Prisoner is not going to be able to do something that matches that tone, as they will be trying to find a place to hide on the ship (if they do escape) or just waiting in their cell. There's going to be a disconnect between the two groups of players, and the ones who are actively contributing to the story are going to have a lot more fun.
So with that in mind, here are two options that spring to my mind to improve the story:
1. Have The Prisoner Be An NPC You're right in assuming that 'Vague Dragon' is not a great threat. The key is making things personal. Look at the backstories of your PCs, see if there's anyone they care about (if they don't have them, which is not usual in new groups, ask them about it before or during the session: "Hey, what was the name of your friend from the Borderlands Keep, the one who used to tell all those bad jokes while you were on patrol?" "Doesn't your sister live in this town?" etc.). THERE is the seed of investment, which you can use to build a story. Don't just kidnap them right off the bat, though; that breeds "Street Orphan Murderhobos", players so scared that any connection they make will be exploited by the GM that they don't have any human interactions at all.
So think about this: The party goes to Waterdeep to sell some of the loot from that dragon's hoard and sniff out some new jobs. One of the players has a brother named Boris who runs a tavern in the inn and has volunteered to put them up for a few days.[footnote]A good trick for making NPCs seem real is to give them a defining motivation/characteristic that you can reference whenever they need to make a decision, and also to add some flavour to their actions. This works best if you combine a body part with an adjective or other short description. For Boris, the phrase is "Hands Full of Food"; he's a warm and caring person who loves taking care of other people and making sure that they're happy, and whenever he's not bringing out armloads of dishes for his customers and friends the big man is almost certainly enjoying a snack of his own.[/footnote] Over a meal of his famous spiced potatoes, served by his daughter Natasha (Shy Smile), Boris tells the party that there have been a number of kidnappings in the dock area over the past few months, and the city has offered a reward to anyone who can find out who is responsible. The PCs look into it and realise the attacks are following a pattern, moving across the city in a grid; Natasha here's the party talking about it and mentions that she saw the same mean-looking clam salesman in each district in the days before each kidnapping (who scouts the area for the criminals). Our heroes go and intercept the kidnappers, catching some of them in the act. They confess (to the PCs directly or the city watch) that they work for a human trafficking ring bringing subjects to Thay for experimentation, under the orders of a cruel elf woman with a sinister scar across her mouth who commands a pirate ship called the
Red Mercy. They next day they go to City Hall to collect their reward and follow up with the hostage rescue being planned by the city, and when they return to Boris' tavern they find him lying by the broken door, bleeding from the scalp and moaning that they took Natasha right from his arms.
Now the PCs have a clear goal (rescue the hostages from the pirates), a way to accomplish that goal (join the Waterdeep vessel going to find the
Red Mercy, though they may have their own ideas of how to find and beat the pirates which should be supported) and a good personal motivation for doing so. Everyone gets to take part in the high seas adventure.
2. Set the Prison Somewhere Else, And Talk To The Player In this scenario, you go ahead with the kidnapping idea. First things first, you talk to the player you want as the 'victim' and ask if they would be OK with their character being taken prisoner, knowing that it will put them at a disadvantage. If they aren't 100% behind the idea, abandon it; it's not worth making 1/3rd of your players unhappy.
You also restructure where and how they are being taken to allow that player more options. Maybe instead of a pirate vessel, they are taken to a slave mine where the overseers don't care what happens in The Pit, so long as the gold keeps coming up. The player meets some other prisoners and works with them on an escape plan while also dealing with the 'toughs' who prey on weaker prisoners, and the rest of the party races across the desert to help extricate the player and conveniently arrive just as the escape plan goes into action. Maybe the player's prison is actually a magic ship in a bottle, an extraplanar vessel that they crew with other prisoners and have to deal with all kinds of strange creatures while they sail for the Cork, hoping to break free, while the bottle is carried on a real pirate ship that the rest of the party is chasing. Heck, just a set of Sending Stones so they can communicate with the party and coordinate would be a big help. The PC is being put into a difficult situation, don't make them powerless to boot; give them the freedom of a big cage with plenty of other people to interact with in a variety of ways, from friends to rivals to enemies.
