"[OC] Campfire" by Kleoite (resized) is licensed under CC BY-NC-ND 3.0
Attraction sometimes enters the realm of courtship. If characters are on their own in a fairly open society, wooing might not be difficult, lengthy, or even required at all. Characters could meet privately, even without being properly introduced, and engage in sex without much censure. But in many societies, people watch and keep couples from being too free with each other. Families want to be involved, and friends take offense if codes of conduct are breached. If you're looking to add a sense of chivalry and lawfulness to your game, this can be a way to do it. Courtship is usually a path to marriage, but it can also be the acceptance of a lover in someone's life – and it can involve all kinds of quests and rituals.
The early stages of courtship tend to involve keeping a couple in the public eye while they start to get to know each other. A suitor might be involved in a family function, which in D&D could be everything from a party to a joust. A chaperone might be sent along if the couple goes out together, and there's nothing like your Uncle Paladin to put a damper on an evening. A suitor might be expected to attend functions with other suitors, which can be highly entertaining. The point is to see if the couple and family approve of each other, and yes, to prevent sex from happening too soon. It might seem outdated to some of us, but it can be a fun point to add to a game. And other player characters can easily be involved in such scenes because they are so public.
Later stages of courtship allow for more private visits and a few more liberties. They might also involve challenges and quests. Parents might expect a dowry, or the head of a fearsome creature, or a magic item. They could require a suitor to avenge a slight or act as a diplomat for the family interests. Slowly but surely, so long as they pass muster, suitors should be drawn closer and closer to their love and to marriage. (For a more modern example of courtship, watch the way that Michael Corleone woos his Sicilian bride-to-be in The Godfather. Courtship doesn't just happen in knightly stories.)
For lovers who can't be seen together, hidden intimacy can be exciting and dangerous. It involves sneaking away, meeting in remote places, and sending private messages. Skills to lie, disguise oneself, hide letters on one's person, and go unseen around can be as useful for sneaking around a city as they are for sneaking around a dungeon. Magic can be used to ensure privacy, send messages , slip past guards, and make use of out-of-the-way places. Class and race abilities can come into play, as well. A mini adventure can involve being able to spend time with a vampire suitor before the break of day, a la Romeo.
While advanced options can make these things easier, they aren't fool-proof and can get expensive. A character can use something like a flower code, in which flowers have different meanings based on their type and color. These meanings will likely have local significance; trying to use the flower code of another region could lead to a hefty penalty on a communication roll. Why bother with this method at all? Because without words, a lover can deliver messages about a wide variety of things: faithfulness, being wrongly accused, apologies, doubts, jealousy, initial fascination, determination to win affection, reassurance, meeting location and time, warnings, disappointment, disapproval, and offense. (For a more in-depth list, click here.)
If worse comes to worse, a couple might need someone trustworthy to pass messages back and forth. A servant is a traditional choice, like Juliet's nurse, but bards easily get involved in such entanglements. A couple might find each visit a sympathetic cleric, or an unassuming sorcerer. Adventurers might help other members of their party, not only by passing messages but also by giving reassurances. This can be a good way to get more than two characters involved in a courtship.
Those who haven't been able to find a worthy suitor on their own can call on matchmakers to help find someone appropriate. Bards and rogues can make excellent matchmakers, since they are often adept with social customs and up to date on local gossip. They can even navigate family trees to find the most profitable matches, if that's what's desired. A cleric might be sought if the client is devout and wants to make a match with someone who follows the same deity. They might offer divinations and dream interpretations to discover who the deity wants as the client's spouse. Followers of certain gods - namely those dedicated to love, marriage, and family - may be more inclined to act as matchmakers, as well.
Matchmakers who are approached by parents (authority figures) in strictly traditional places may be pressured to fulfill the wishes of those in power over the desires of the candidate. In these cases, the family has a lot to lose or gain by a match, so the larger social, economic, and political concerns are paramount. It's not that romantic love doesn't matter at all, but it probably isn't expected; if it happens, it's a happy side-effect (and perhaps a sign that the matchmaker went above and beyond to find the right person). It's still a good idea for a matchmaker to learn the candidate's wishes for their future spouse because if they're pushed into a miserable match, it could be blamed on the matchmaker and earn enmity down the line.
When candidates approach and pay for matchmakers on their own, they have the most influence over how things proceed. A character could approach a matchmaker upon reaching a certain age, discovering a desire to have children, or taking a friend's recommendation. They might be in the market for a long-term companion, a strong addition to a polycule, a parent for their children, or a mate they don't have time to find, with or without marriage entering the mix. Whatever they decide informs the matchmaker's approach, and candidates retain final say on how to proceed.
Matchmakers are by no means perfect, so they tend to introduce various candidates over time and gauge how bonds develop or fizzle carefully. They may get to know candidates' families and friends to learn more about them and may rely on social connections they already possess to find suitors. But if their recommendations fall seriously short of expectations too often, their reputations suffer, so they work hard for amicable meetings. How much they can expect to be paid depends on things like their reputation, the methods they employ on the candidate's behalf (skills, spells, magic items, artifacts, etc.), and how satisfied the client is with the result. A matchmaking NPC or PC can be a valuable and fascinating addition to a social and/or political campaign because of just how connected they can become - and the unusual quests that can result.
Though it may sound tedious, there are many reasons that societies support courtship before sex and marriage. Parents value the safety, innocence, reputations, and futures of their children. Friends care about supportive, healthy relationships for one another. The upper crust has the most to lose through marriage, since they own so much to begin with, so they are likely to put extra weight behind protracted courting. And it must be said that some people just want to control others and make demands out of selfish interests. Choose the flavor of courtship that interests you the most and makes the most sense for the setting and go with it.
When a couple has proven themselves ready and worthy, they will often be urged to marry so let's talk about that next.
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