Dungeons, Dragons, and Date Nights

Welcome to the love quest.

Dungeons and Dragons is a game designed to be played with friends, but the game is quite malleable and can easily be adjusted to any situation or setting. This is, in fact, one of the best qualities of the game and a primary reason why it has accumulated such a large following. If you and your loved one desire a more intimate setting to explore the game as a couple, then this guide should serve as an outline to create your very own love-themed adventure.

First: the premise.

The story behind this adventure is that one member of a loving couple (you, of course) has decided to set up an adventuring challenge for their significant other. This challenge will feature wholesome memories, precious moments, reminders of the trials of love, and some pretty adorable monsters. You can come up with your own backstory that makes the challenging work. Did your character have a buddy in an adventure training guild who was able to set everything up, or is your character a high-class wizard who is using magic and illusions to set the scene? Also, take liberties in describing the setting you want. It can be a high-fantasy realm with goblins and elves and dragons flying above, it can be set in the far reaches of space, or it can take place right there in your living room! Anything goes in this game, just have your idea in mind as you play.

Step 1: Character Creation. There are several ways to approach character creation in D&D. There are races and classes from the book and homebrew options out the ying-yang. There are no limitations on the character that you can create for this game, but for an added step of romantic fun, I recommend a few special settings.

Instead of rolling for stats, create a fun personality quiz for your partner. Their responses determine their stats. For example, you could create situational questions about strength, wisdom, or charisma to see how many “points” they can accumulate for each of these stats. See below for sample questions.

You're walking down the street when you see a poor little ogre child getting bullied by a group of human children. How do you react?

Any response that requires talking down the bullies or comforting the victim adds +2 to Charisma

Any response that results in physical violence or a display of strength results in a +2 strength.

Once you finish the personality quiz (or skip it If your partner already has a character from a campaign they want to use), create an additional “love stat” based on how well your partner can answer questions about your relationship. See below for sample questions.

Where was our first date? What was our first trip together? What is my dream job? When did we have our first kiss? Who said "I love you" first.

Once stats are out of the way, character creation typically involves picking appearance, background, personality, et. Feel free to invent your own race, class, etc for this campaign, or use one of the standard character guides already in existence. If you don’t want to dive down the rabbit hole of character creation for a small one-shot, simply assume that your characters look quite similar to how you appear in real life. Most of the background and additional information isn’t necessary for this one-shot because your partner’s character will not be interacting with many NPCs, traveling to far lands, or anything of the sort. c

Step 2: The Hook. There are a few things you can do to set up your adventure. I recommend one of the following.

You have left a letter for your partner’s character inviting them to participate in a special adventure in honor of valentines day (or an anniversary, or any other special moment).

You pretend that your character has “gone missing” and an NPC informs your partner’s character of this “tragedy” and instructs them as to where your character was last seen and how to rescue them.

A strange visitor comes to the city and asks for a display of true love. Upon seeing you and your partner’s characters, the stranger announces that you shall participate in this trial and poofs your character away to lands unknown, then informs your partner’s character that they must prove their love for you in order to be reunited.

Your partner forgot to get you a gift for this special occasion (classic, right?) and so now they are scrambling to pull one together. The quest for the perfect gift sends them on the trials below, and somehow along the journey, they must come up with just the thing to give you when they meet you at the end.

Step 3: Trials: Once you have your hook selected, it’s time to select the trials. I have listed out a few possible “trials” that you can put your partner’s character through. I recommend picking a few for the sake of time. If you want a shorter game, pick one. If you want a longer game, pick multiple. If you can’t pick, roll a D8!

Memory Lane :

A shimmering pink road stretches out before you, as far as you can see. There is a strange fog around the road so you can’t quite see where it leads, and the fog is so dense around the road that it seems impossible to venture through it. As you progress along the trail, you see strange objects from your past scattered across the roadside.

You describe the objects your partner sees. Maybe it’s a football because they were on the high school football team when you first met. Maybe it’s a DVD of the first movie you saw together. Maybe it’s a book you have read together. Whenever your partner approaches one of these objects, they might get a sense of the old memory and you could describe it to them. Alternatively, you could have them describe what they remember.

This could be a good time for a check with that “love” stat. If there was something that your partner failed to remember on that quiz you gave them during the character creation stage, put it on memory road. They can then roll to see if their character can remember the object now. If they pass the roll, you describe the object as you had with the others. If they fail, the object could become animated and attack! (See Monster Section)

That Darn Cat (Or any pet)

Your partner has forgotten to feed the cat (or other pet) for the last time. Now, their unsatiated hunger has morphed them into a giant beast that your partner must fight (or otherwise appease). Be very creative and very outlandish with your descriptions. Give your turtle a giant spiked shell that can be removed and thrown like a frisbee. Give your dog a thundering bark that causes earthquakes. Make your kitten the size of King Kong.

Your partner can either fight to calm down the raging beast or use a clever tactic, like delivering food or singing a lullaby. You choose what works, but model the right choices based on your pet’s personality and preferences.

Obviously, no pets should be harmed in the making of this campaign, so if your partner does choose combat, the battle ends once your pet has decreased by a certain number of hit points, which shakes them out of their rage and returns them to normal size. (See Monster Guide for details). Also, a high enough love save (you choose the #) may calm down the pets earlier on.

The Attack of the Chores

Do you remember the movie The Brave Little Toaster, where all the appliances come to life? Do you remember the sheer terror of seeing that vacuum monster? Now imagine it to the extreme. Vacuums, dustpans, dirty dishes, all of those household chores that you and your partner never get done are coming to haunt you. This is a mob-style battle where your partner must vanquish all the chores.

To personalize this experience, make the chores that you and your partner struggle to accomplish the strongest enemies. Also, be sure to add in as many personal details as possible (i.e. maybe describe the dishes that are actually sitting in the sink right as you play!)

The Runaway Third Wheels

Does your relationship have a third wheel? Or maybe a third, fourth, and fifth wheel? Maybe your entire friend group frequently tags along and you have a full semi-truck each time you all hang out. Regardless, those extra wheels are in trouble, and you and your boo must save them (yet again).

Personalize this one as much as possible. Do you have a friend who frequently gets lost? Describe a maze where your partner must search for them. Do you have a friend who constantly dates the wrong kind of people? Have your partner fight off an army of prince(es) not-so-charmings so you can save them from their poor mistakes. Do you have a friend that’s more of a party animal? Maybe you have to find them at a rave filled with dancing psychedelic hippos (I mean it, be creative and have fun).

If you so choose, you could have the third wheel give your partner a treasure for finding them (see the treasure section) or you could have them tag along and assist your partner as an NPC, or even have them play along because odds are that third wheel is right there with you even now during the game that was supposed to be just for two!

Imposters of Love

Yay, your partner has found you… or have they? It seems as if you have some doppelgangers out there pretending to be you, but can your partner see through their fibs? Or will they fall prey to the imposters of love?

Describe significant memories that you and your partner share together. For example, maybe think back to the first dinner date you had. Describe most of the details; the restaurant/location, the meal you ate, and the weather with perfect accuracy, but change one thing, like the outfit you were wearing or the words you said, or the date of the occasion. Can your partner figure out what’s off about the memory?

With a high enough “love” stat check, you can drop subtle hints and provide more details to help them figure it out.

If your partner fails to uncover the discrepancy in the memory, they must now battle against the fake you. This is when you get to use your own character (if you made one in the beginning) or you can create a character for yourself on the spot. Again, be creative. If you’ve always wanted a glare that paralyzes your victims or a scream that shatters glass, now's your chance. Just don’t make your imposter too powerful, your partner needs to vanquish them or escape to finally beat this love challenge!

A Dream is a Wish Your Heart Makes

Do you have a dream vacation? A dream job? A dream wedding? Here’s your chance to make it happen! Your partner has been transported to this dreamscape, but things aren’t quite how you’ve always wanted them. Maybe there are no more front row tickets in that concert you’ve been trying to see, maybe you’ve sprained your ankle and you can’t complete the hike to the top of Mount Everest, maybe your first day at your dream job is a disaster because you left your briefcase on the bus. Maybe your wedding is in peril because the florist accidentally brought the type of flowers you’re allergic to.

In this challenge, your partner must do everything they can to fix the trouble in your dream and to make sure everything goes exactly as you always wanted, or maybe even better. Again, you can make this more challenging by pointing out what’s wrong, but not telling them what to do to fix it (unless they roll a high enough love stat and you want to give them a boost). This challenge is more of a puzzle to see how your partner can creatively problem solve and how well they know your dreams.

Cupid’s Wrath

What is a romantic adventure without a visit from Cupid? Or more accurate, what is a D&D game without a battle with a giant winged creature with a bow and arrow? For this quest, Cupid is having a rough day. He’s given up on love because he hasn’t seen enough of it in the world. This shift from his normal self has transformed him into Dark Cupid. A hit from his arrow fills people with hatred. He’s been flying around sabotaging happy relationships, and it’s up to your partner to stop him. This quest is an epic battle against the winged cupid. Hopefully, your partner's love/constitution modifiers are high enough so they don't fall victim to Cupid’s evil reign. See the monster guide for details.

Create your Own Adventure:

You know your relationship better than anyone, so only you can design the absolute perfect quest for you and your boo. Time to put on that thinking cap and come up with your own loony tale.

Step 4: Treasure! What is a quest without treasure? You can throw these rewards in at the end of each quest (if you play multiple) or scattered in between if you’re playing one. The treasure should be geared towards helping your partner defeat upcoming challenges and continue on in their quest to reach you. The treasure can also mirror gifts you have given them in the past (or that you may give them in real life during the course of the game, talk about bringing the game to life!) The following are some ideas for treasures, but as with everything else, try to bring your own love and experiences to the table and do what best suits you and your relationship.

True Love’s Kiss

That’s it, a bottled-up kiss. Opening the jar will release the kiss in whatever direction the jar is pointed. A true love’s kiss has some pretty potent power. I’d say it can quell just about any enemy that’s feeling a bit unloved (like, for instance, a raging pet from quest 2, or dark cupid from quest 7). Use it carefully though, there is only one kiss per jar.

If you want to be ridiculously sappy, you could blow a kiss into a small bottle and hand it to your partner when they release this item, and then when they use it, you could surprise them with a real-life kiss too. MWAH!

The Scrapbook of Love

Do you and your partner love to keep a fun record of your adventures together? (or have you been building one as a secret surprise?) Why not give them the scrapbook in-game. Your partner's character can look at images that depict the events of the past, and these images might even jog their memory about past events (especially with a high love save roll). This book of memories might prove extremely useful in fact-checking memories in quests 1 and 5!.

A Delicious Treat

Describe your partner's favorite dinner or dessert (bonus points if it is in the oven now and you’re about to bring it out!). Your partner finds this food. Eating the food counts like an instant long rest (healing, restoring spell slots, etc). It might also boost some of your partner's stats to help prepare for future fights (you can choose which stat and by how much based on what you think your partner needs most, but I recommend a smaller boost here, like a +1).

The Well-Loved Jacket

Does your partner have a favorite article of clothing, like that old jacket that has two dozen holes in it but is still somehow always the go-to choice when the weather gets a bit nippy? On the other hand, do you have a brand new T-shirt you’re waiting to give your partner? Whatever the case, make that special article of clothing a top-tier suit of armor. An instant +2 to armor class and a 10/10 on the style scale! (JK, there is no style scale in D&D…unless you make one).

The Fuzzy/Scaly/Feathered Side Kick

Every classic Disney princess has an animal sidekick, why should a D&D adventurer be any different? If you’re partner successfully calms the beast in Quest 2, you can have your adorable pet tag along on the rest of the journey. I suggest treating your pet like a support spell that best suits them. (I.e. a dog’s bark might count as bardic inspiration. A turtle could give an armor boost. A cat’s hiss could harm the enemy like vicious mockery)

The Best Friend’s Lucky Sock

Or any other lucky charm or classic keepsake. This item should come from the third wheel your partner rescues in quest 4. Maybe it’s the best friend’s lucky sock. Maybe it's their baseball bat that can count as a weapon. Maybe it is keys to their car that your partner can use to traverse across memory lane at high speeds or drive off a cliff to launch at dark cupid (this is a game for creativity and thinking outside the box, is it not?). Anyway, wherever item you choose, have it be sentimental and give it a modifier that fits its description.

A Photo Locket

So a picture of you can always stay close to your partner’s heart (cue the chorus of “awwwws”). Or any other cute sentimental gift- a bracelet, a tattoo, a heart-shaped stone, etc. Make this a positive modifier to the love stat. I recommend +2, but you can go higher or lower depending on what you see fit.

Step 5: Monsters

An important thing about creating any monsters is that you have to level them appropriately. Now, there are currently no level restrictions on what character you can use for this one-shot because it's always fun to make it more open. However, it is important to decide on a character’s level to get his or her proper stats, feats, spells, etc. Once you have a character level, you need to select a monster level. The typical challenge rating in D&D tells you how tough of a monster four people of one level can manage. For example, a challenge level of 3 means that four level three characters will be able to beat this monster. You will want to significantly reduce the challenge rating of your monsters because this one-shot is for a party of one. Check out the official D&D rule book for help setting your monster’s difficulty.

That Darn Cat

This is your beloved pet, so this monster of course is going to require you to be very creative. Give the pet stats that reflect its personality. For example, an exuberant young border collie puppy will have extremely high dexterity and one of its attacks could be a whirlwind whipped up by a wagging tail while a box turtle is going to have an extremely high armor class and might have a ferocious bite attack. Since this is a boss battle, make it difficult and have an opportunity for your partner to heal at the end.

Each pet should also have a “secret solution” or a way to calm them down without a fight. For example, an oversized hyperactive kitten might be quelled by distracting her with a fluttering flock of birds and using the monetary pause to fill up her food bowl with her favorite kitty chow. Be creative, and only have this solution work if your partner rolls high enough on a love save.

The Villainous Vacuum

Or any other chore item, you name it. This foe should be tough, but not nearly as tough as a boss because it will be faced in the company of other chores. Give it enough health that it takes two or three hits to knock it down and give it some fancy attacks too. A vacuum might suck up your partner’s weapons. A dustpan might shake out a swarm of creepy crawlies, and a dirty cat litter box could release toxic odors that poison your partner.

A Swarm of Dirty Dishes

Create a group of smaller foes to also battle your partner in the chores quest. These foes should be easy enough to take out in one hit and they shouldn’t take out more than 5-10% of your partner’s health with any hit, but there are a lot of them so they should be annoying. Half a dozen dirty dishes spitting sud bombs, random articles of clothing that reach out and restrain your partner, etc. Your partner can either encounter these chore monsters separately or in tandem with the stronger chore monster as well.

Fake Love

The imposter of love should be one of the toughest foes on the board. This should be a 1 v 1 fight against your character. Give this one stats that reflect you and attacks that reflect you. However, any “love” attacks against this imposter will be double effective. (Be creative with this. A “love” attack could be a love ballad from a bard, or your partner shouting out a declaration of love for you as they plow their blade into the heart of your look-alike.

Dark Cupid

Another tough boss battle, this one especially because your partner either needs range attacks, or a clever way to keep Cupid grounded. Cupid flies around the area and shoots arrows. The arrows decrease your partner’s love stat and/or constitution. They might have long-term effects that hinder your partner in future quests unless remedied.

Step 6: Victory

Congratulations, your partner has finally defeated all of the trials they have faced and reached the end of the quest. Write a little ending that matches what you chose as your beginning hook. Might I suggest also having a nice dinner ready for this fearless warrior as a feast of celebration?