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wafflefries13 · 3 days ago

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First Date Ideas (Multi TWST Cast X Reader)

Summary: Short drabbles of where you would take your favorite Twisted Wonderland guy on a first date, and where he would take you.

AN: Pseudo part 2 to the asking-out fic I posted. Not really much else to say besides I really liked trying to come up with a bunch of unique ideas. Thanks for reading!

Cross-posted on my AO3 TheGhostInTheKitchen

Warnings: Fluff

Part 1: Asking them out

Ace:

Where you take him: Arcade

It’s fun, it’s cozy, it’s classic, and it gives Ace a chance to show off. You both get a bunch of tokens, eat greasy pizza, and try your hand at the games. You take each other on in skeeball and Ace tries to convince you to go against him in the basketball game but you argue he has an unfair advantage. So you settle for the racing simulator. After, when you collect all your tickets, you pour over the prize counter, probably ending up with something not very impressive, or maybe a snow cone maker that stops working after the first three uses. But you’ll treasure it since it’s loaded with memories.

Where he takes you: Carnival

This boy is already a clown, put him back where he belongs. Besides the fact that it gives him an excuse to impress you by winning prizes at the games alley, or trying to anyway, a carnival date fits Ace’s high energy. You can share popcorn and cotton candy while watching the circus acts and Ace will whisper to you explanations for the tricks the magician uses. There’s plenty of stuff to do and tons of fried food. It’s a classic for a reason. And he’d love it if you hold on to him on the rollercoasters. He ends up screaming more than you.

Deuce:

Where you take him: Petting zoo

I just want to see Deuce fawning over baby chicks, is that so much to ask? NGL, I think he’d love it. You could go to some sort of tourist farm and check out the cows getting milked, sheep shearing or sheepdog herding, and collect eggs from the chickens (the kind that don’t hatch into chicks). I can also see Deuce getting into a grudge match against a goat that keeps bonking into his legs with his horns. At the end of the day you’ll sit at a picnic table eating some treats made at the farm and watch the sunset.

Where he takes you: Botanical garden

Deuce would want to do something classic, a surefire, tried and tested dating spot. I can imagine him being nervous, getting you flowers when you are already going to see more flowers. You’ll hold the flowers in one hand and Deuce’s, slightly sweaty, hand in the other. If they have a butterfly room, even better. They’ll have a little booklet with different species and you and Deuce go on a scavenger hunt to identify as many as possible. Winner gets kisses.

Trey:

Where you take him: At home food science experiment kits

Did you ever see those at home science food kits where you made gummies and foam and other candy, usually themed to something really weird like monsters or worms? Yeah, you do those, half making fun of how weird it looks and half marveling at the cool effects of swirling all the different ingredients together. Will they taste amazing? Probably not, but Trey probably knows a few cool tricks to make everything a little more edible.

Where he takes you: Chocolate factory tour

Have you ever been to Hersheypark in Pennsylvania? There’s a whole section with a little dark ride that shows you the history of chocolate (that’s worse since they took the singing cow animatronics out), a cute interactive play, a trolly ride with chocolate samples, and two chocolate making experiences. You can stuff a giant Reese’s Cup (which is way too sweet IMO) or design your own chocolate bar including the wrapping. Anyway, there’s probably not a one-to-one replica, but with all that magic you can’t tell me there’s not something Willy Wonka-esque. You’ll both spend the day learning about the history of chocolate and chocolate making in Twisted Wonderland, capped off by making all kinds of treats. You’ll experiment with typical flavors, like raspberry, caramel, and nuts, to the more extraordinary, like jalapeno, lavender, and cheese. In the end, you’ll go home with a full box and a picture of the two of you, melted chocolate smearing your faces. (Trey will remind you at least three times to brush your teeth properly after all that sugar.)

Cater:

Where you take him: Thrift store

Listen, you find the right thrift store and you can find amazing treasures. And if not, well, you still find weird, kitschy stuff you can have fun ogling. You and Cater will take turns finding the best and worst outfits in the thrift store, having a makeshift fashion show by the changing rooms. Cater would, of course, take plenty of pictures for Magicam, labeling them #MeetMyNewPartner, #HeightOfFashion, #BestLookingCouple. You’ll also look through the aisles, coming up with backstories for all the various objects people have donated over the years. Whether or not you actually buy something isn’t the point. You end the day with plenty of pictures and at least three inside jokes that will drive everyone else crazy.

Where he takes you: Crafting class

There’s been an emergence of cute crafting stores. Make your own bag, make your own candle, paint your own pottery, make a phone case, rug tufting, that kind of thing. Not only are they a cute and totally Magicamable couples activity, it also gives you both something to take home at the end of the day. Whichever you do, I can see you both making a craft for each other. Maybe you keep what you’re doing a secret until the end, filming your reactions when you reveal your crafts. If you pay close attention later on, you can catch him quietly admiring your gift.

Riddle:

Where you take him: Escape room

Back during the NRC Halloween event, when everyone was stuck in the ghost realm, Riddle had a ton of fun solving those puzzles. I think he would love an escape room, finding clues and undoing locks, using logic and guile to uncover the story. He might get frustrated at the harder puzzles, but it’s all worth it when you work together to solve everything. You get your picture taken together with a “We Escaped!” sign that you frame. It would be something unexpected but fun for the both of you. (TBH, I think he would love the Nancy Drew games. Maybe not the part where you keep breaking into people's things and stealing stuff, though.)

Where he takes you: High tea and window shopping

Riddle is going for a classic, something prim and proper for a prim and proper boy. I can see him reserving a table at a high class hotel for high tea, a table set with a beautiful porcelain teapot and a tower of tiny sandwiches and cakes. He’d order a bunch of different teas you could try. Afterwards, you would walk along the street, checking out shops and talking together. Bonus points if you both get to wear something fancy and cute.

Leona:

Where you take him: Picnic

Look, while having the title of Ramshackle Dorm Prefect sounds fancy, you don’t have a lot of extra cash. You would need to do something simple and cheap but still meeting Leona’s royal tastes (You can’t tell me this boy isn’t a picky eater.) Thanks to the Culinary Crucible, you have a few new skills to test out. You find a big blanket in some old trunk in Ranshakle and pack everything together in a cute wicker basket. Maybe you’ll eat in the gardens where Leona always takes naps or go out on the beach to watch the waves. You both end up falling asleep with full bellies. (Leona won’t admit it, but he feels like that was the best food he’s had in a long time.)

Where he takes you: River cruise with a fancy dinner

Leona is going to see your cute picnic date and immediately one ups it with a super fancy and elegant river cruise with a full five course meal. It’s on a beautiful private yacht sailing down a river in the Sunset Savannah. You’ll sit on the deck, candlelight table, while perfectly dressed waiters serve you. This would probably backfire on Leona, though, as you tease him for acting the most prince-ly you’ve ever seen him. Not that you don’t have a ton of fun. By the time dessert rolls around, you’ve both ditched the fancy setting and started skipping stones in the wake of the boat.

Jack:

Where you take him: Canoeing

Something relaxing and outdoorsy and fun. I’m thinking you’ll find someplace like the Ocklawaha River or Crystal River in Florida. A beautiful river with plenty of turtles and fish to spot, surrounded by lush forests or Everglades. If you’re more confident on the water, maybe you each can have a kayak, but I imagine something like you both share a boat. It would be fun to have a sort of eye-spy sheet, like who can spot the most turtles, identify fish, maybe catching sight of a manatee, and, wait, was that an alligator? You’ll end your journey at a natural spring. Dumping your stuff in the canoes, you’ll jump in and spend the rest of the day swimming in the cool water. Maybe you find a good vine or rope and swing out over the water.

Where he takes you: Zip Lining and high ropes course

More high energy and involved than a lazy day river trip, but it gives you two the chance to be close. I can almost guarantee Jack found out about the place you go to from Coach Vargas. You’ll get hooked up into harnesses and climb up to a vast network of bridges and ladders and obstacle courses hung between the trees like a giant athletic spiderweb. Maybe at one point you slip, and, although you’re perfectly safe with the harness system, Jack still lunges forward to catch you, blushing hard after as he realizes how close you too are.

Ruggie:

Where you take him: Food festival

I imagine something like the Plant City Strawberry Festival, the Wilton Blueberry Festival, or the Gilroy Garlic Festival. Heck, even throw in the Epcot Food and Wine Festival if you want to have another Disney reference. Something county fair-like with plenty of free samples. You’re not sure who convinced who, but at some point you end up getting those cheesy headbands with springs on top and plastic versions of food bobbing around your heads. There always seems to be sketchy fair rides at these things, too, so you definitely cling to each other going down a log flume ride, kind of regretting how much you ate beforehand. But that’s not going to stop you from chowing down after.

Where he takes you: Farmer’s market

Listen, if something is good at a farmer’s market, then you know it’s the best. The big ones not only have plenty of great food, but also local performers and plenty of fun extras to buy. Even if you don’t want to buy anything, it’s fun walking through the crowds and seeing all the different stands. You definitely get some super fancy ice cream, probably with some ridiculous flavors like lavender, parmesan, or licorice. Serving sizes always seem huge too, so you both definitely go home with plenty of leftovers. (You totally don’t notice that Ruggie has been paying with Leona’s credit card this whole time.)

Azul:

Where you take him: Game shop

One of Azul’s vignette stories has him practicing throwing dice so many times until he’s able to completely control what numbers will come up. Sure, he might be in the board game club for fun, but also because he likes to win. So a game shop that hosts weekly game nights would be perfect not only for him to show off and impress you, but also a cozy space to have fun and take the pressure off first date jitters. Whether you have a game with just the two of you or join in with other patrons there, you can team up to strategize and win. I personally think something like One Night Werewolf would be perfect. (He does feel bad when he accuses you of being the werewolf, though. Too bad he’s right.)

Where he takes you: Fancy restaurant

It’s nothing compared to the Monstro Lounge, of course, But Azul is putting his best foot forward with a classic first date spot. Azul plans everything down to the most minute detail. He double and triple checks the menu of where you’re going before you even leave to make sure there’s nothing you’re allergic to and there’s something you’ll like. He goes all out: flowers, pulling out your chair, getting a bottle of something fancy and expensive to drink (non-alcoholic if you prefer). Of course, the moment you start complimenting him he turns red and starts tumbling over his words. Maybe you lean into that, enjoying teasing him, the switch from having everything under control to a mess of complex emotions. Still, you slide your hand across the table taking his, and you both have a perfect night.

Jade:

Where you take him: Make your own tea blend shop

Jade is an experimental guy. I think if he wasn’t the founder of the mountain lovers club he probably would be in the science club just to mix together every kind of chemical just to see what happens. You would take him to a small tea shop, maybe in town on Sage’s Island or somewhere else through the mirror portal. You would pick out matching tea cups then choose different flavors and leaves from the jars of dried tea. You could make up little packets of different custom blends, some of them stuff you actually think would taste good, some that just sound interesting all together. You and Jade could trade and drink them together back at the Monstro Lounge.

Where he takes you: Mountain and cave hike

This is kind of a gimme, but I think he’d want to show off all his knowledge of local mountain flora and fauna. He’s the only member of his club, which gives you plenty of time to be alone together and use the club’s budget however you want. He would surprise you by showing you an undiscovered cave entrance. Hopefully it’s not the kind where you have to crawl on your belly to get in. I like imagining something like Ruby Falls in Tennessee. He’d bring you in, turn off his lantern, and crowds of bioluminescent mushrooms would glow around you.

Floyd:

Where you take him: Roller derby

You can’t tell me this boy would not absolutely love watching a bunch of people going super fast while trying to beat the hell out of each other. He would immediately pick a favorite team and buy all their merch. Even if it’s just a small local circuit he’ll make his own merch for the two of you to wear while you cheer them on. Floyd already likes shoes, specifically sneakers, so I think he would really like the idea of roller skating, going as fast on land as he can in the sea. Your next date will be at a roller rink.

Where he takes you: Laser tag

Similar to going to a roller derby, Floyd would love the energy and competition of laser tag. He’d be vaulting over the barriers and launching sneak attacks against other players. Maybe you two would team up and top the leaderboard or maybe he’d hunt you down in the glow-in-the-dark black-light game room. Afterwards you can catch your breath in the lobby and eat junk food. You’re not sure if you’re excited or nervous when he mentions paintball.

Kalim:

Where you take him: Hands-on science museum

Coming up with a first date idea to impress Buys-A-Restaurant-Chain-Because-You-Said-You-Liked-Their-Breadsticks-Once-Kalim is a little harrowing. Sure, you know he would like whatever you have planned, it’s the thought that counts, but that doesn't mean you don’t want to try and show off a little. You eventually find a hands-on science museum. Think the Franklin Institute in Philadelphia or the Tech Museum of Innovation in San Jose or even WonderWorks. It’s something that keeps you active, jumping from exhibit to exhibit to try out all kinds of new things while pretending you're learning. Sure, most of the other people there are kids, but that doesn't stop either of you from having fun. With Kalim’s experience with all his younger siblings, you soon have a small army helping you with the replica dinosaur dig site.

Where he takes you: Fused glass class

Kalim’s first instinct is to go big. Throw a parade, rent out a theme park, buy a private island. This little ball of sunshine is way too excited to think anything through. Maybe Jamil mentions that you might be intimidated by such an overwhelming show of wealth on a first date, or maybe he implies you need to work up to something that extravagant. Whatever the case, Kalim agrees to start small. He’ll take you to a stained glass shop that offers classes in Silk City. You’ll take a fused glass class together, where you take shards and rods of other colored glass, placing them gently together in a shape. The owners fire the final product leaving you with a beautiful hand-made ornament. Kalim hangs it by his window back in his dorm room, smiling whenever the light catches it. (He’s still thinking about that private island, though.)

Jamil:

Where you take him: Aviary

Jamil mentioned in one of his vignettes that he would want to own a parrot one day. So why not give it a test run with a variety of different parrot species, and throw in some parakeets, falcons, lorikeets, and canaries while we’re at it? You buy cups of food and the birds will fly down to perch on your arms and heads. The parrots, in colors ranging from green and yellow to blue and purple and red, show you how they dance and talk. There’s a game you can play with them where you hold up different objects and they’ll tell you what they are and what they’re made of. There’s even a falconry show where the birds swoop out into the audience. At the end of the day, the tour guide makes a joke about lovebirds that you both pretend to ignore.

(BTW, did you know President Andrew Jackson had a parrot that cursed so much it had to be removed from the room during his funeral because it kept swearing? The more you know.)

Where he takes you: Dance class

Mr. Jack Of All Trades, Master Of All over here is definitely going to want to show off. No matter who asked who out first, he wants to reassure you, and himself, that you made the right choice agreeing to go out with him. So he sticks with something he knows best, something he has fun with, and something he can easily introduce you too. Whether it’s a classic ballroom dance, salsa, or classic Scalding Sands folk dancing, Jamil just loves the chance to be close to you. It might be better if you have two left feet so he can show off leading you. By the end, you're both sweaty and exhausted, muscles aching pleasantly, but you're also both laughing and wondering if you should enter a couples dance competition.

Vil:

Where you take him: DIY spa night

Like I said before, you don’t exactly have a lot of extra cash, so I can see you relying on a lot of DIY tricks. You’re hoping to impress one of Twisted Wonderland's biggest triple threats with scented candles (bought half-off at Sam’s), homemade avocado hair masks, coconut oil and honey face masks, and a jade face roller and gua sha set you have no idea how to properly use. Vil definitely appreciates effort, so he’ll love whatever you have set up. He’ll even show you how to actually use that jade roller and gua sha.

Where he takes you: Private movie theater

Let’s be honest, Vil isn’t exactly the most humble person. And you, a magicless student with pretty much no frame of reference for any pop culture or just plain cultural insights in this new world, are in the perfect position for him to show off. Vil would rent out a private theater showing the best and most iconic movies in all of Twisted Wonderland. Of course, he also shows you all of his films (Like I said, not so humble). He may give you the side eye when you insist on sharing a bucket of buttery popcorn, but if you gasp and laugh and applaud in all the right places I don’t think he’ll mind.

Rook:

Where you take him: Art museum

Quelle beaute! No matter what kind of art museum you choose, modern, sculpture, impressionist, classical, whatever, Rook is sure to love it. He’d be the kind of person to carefully read each plaque to discover more about the artist and what inspired their work. He’ll praise each and every piece, only to turn around and compare it to your beauty. While this definitely will get you a few looks from some of the other visitors, you won’t mind because you know he’s being completely sincere with every word. At the end of the day, you’ll probably end up with an art book from the gift shop and you get each other prints of your favorite paintings.

Where he takes you: Zoo

You can take the boy out of the hunt but you can’t take the hunt out of the boy… Or something. We know Rook has a penchant for stalking the poor beastman students at NRC (I bet they have to warn the Savannahclaw first years every year), so I think he would also love admiring animals in a place where you’re actually suppose to watch them. Extra points if there are baby animals. Extra extra points if the zoo has one of those programs where you can go back and get close up encounters with some of the animals, like sloths or elephants. You both definitely get plushies of your favorite animals after.

Epel:

Where you take him: Motorcross

Give the farm boy blood. We know from his dorm uniform vignette that he can ride a blast cycle. Checking out a motorcross race or just a show exhibition would be a high energy outing for you both. Cheering in the stands gives him a chance to cut loose from the stricter rules of decorum in Pomefiore, and sometimes it’s just fun to watch things go fast with a chance of crashing. Maybe you can rent one, or borrow one from Ingenhyde back at NRC, and go for a drive. He’ll probably go a little too fast, maybe from nerves or excitement or just to have to hold him a little tighter.

Where he takes you: Ice skating

Do you know how to skate? Great! He’ll take you out to a frozen lake in the middle of a beautiful forest near Harveston. Some place only the locals know about. It’ll be something right off a Christmas card with glitter snow and a perfect clear blue sky. Don’t know how to skate? That’s fine too! You’ll go to an indoor rink, somewhere where the ice is guaranteed to be smooth and won’t crack under your feet. If you’re just learning, please hold on to him and let him teach you, it’ll make him feel super manly and swell with pride. No matter where you go, you both get hot apple cider after, maybe cuddling together in front of a warm fireplace and sharing a warm quilt.

Idia:

Where you take him: Cat cafe

You’re going to need a good excuse to get Idia out of his room, and this is a pretty good reason. Ideally, you would find a place like Tashirojima, the cat island in Japan, but a good old cat cafe will work just as well. You’ll find the least busy time to go which should help Idia’s social anxiety. But once you both settle into plush low chairs and get surrounded by cute kitties, he won’t even notice anyone else. The cafe sells cute frozen cat treats shaped like cat paws that you buy to encourage the cats to come closer. You snuck in some catnip, and you both spend the day enveloped in cute warm kitty cuddles.

Where he takes you: Video game night

The boy is a nervous wreck around other people on his best days, so when he decides to venture on a date he’s going to go with something he’s most comfortable with. You’ll camp out in his room for the date. He’s gone to great lengths to make it nice, plenty of snacks and soft pillows and blankets. He’ll introduce you to some of his favorite but entry level games first. Maybe something Animal Crossing adjacent, but I have a soft spot for point-and-click adventure puzzle games. Eventually, you’ll end up playing doubles on something more action oriented, Idia showing you all the best tricks and combo moves. (Ortho is secretly taking pictures to show at the wedding he’s already planning for you both.)

Sebek:

Where you take him: Salmon fishing and grill

You like it because it gives a chance to get out in nature and be alone together, he likes it because he gets to catch his favorite food and prove he can be a provider. Sure, it just might be a first date, but Sebek likes to think ahead and he’s definitely taking your budding relationship seriously. You two go out into the woods, probably near where Camp Vargus was held, and set up next to a river. While most of the day is hanging out on the bank and talking, there’s always a jolt of excitement when one of your lines starts to tug and you pull out a beautiful gray and pink salmon. Sure, there was that one time when the fish slapped Sebek with his fin until it slipped from his hands, but you both agree to forget about that (you don’t forget, in fact you think about it often). Around midday, you both realize you’re kind of squeamish when it comes to cleaning fish. Sebek puts on a brave face and cuts them up while you make a campfire. Is it the best meal you’ve ever had? No, definitely not. Are you picking fish bones out of your teeth for the rest of the evening? Yeah. Did you two have a ton of fun and are already planning your next date? Of course.

Where he takes you: Tournament

Does Twisted Wonderland have Renaissance fairs? Who knows, but considering Briar Valley still has knights, they definitely have tournaments. The Bead Brawl is sort of similar to what I’m thinking, but there’s more of a focus on what we would think of as traditional medieval events. Stuff like jousting, sword fighting in full armor, and archery. I don’t think you go all the way to the Briar Valley for this, it’s probably more of a smaller local fair with less serious competition. I think Sebek will be a spectator at this event, but that doesn't stop him from commenting on the participants. He tells you about his own training with Lilia and Silver. He’ll be boastful and loud, but you know him well enough at this point to tell he’s nervous under all the bravado. He wants to make sure you’re having a good time but is too stubborn to actually ask. There are definitely giant turkey legs, homemade soda and mead, and chimney cakes to stuff yourself with. He’ll enter a visitor competition, something fun and light like an obstacle course, and win you a prize. At the end of the day there will be a traditional dance at the fair and you both twirl together under lantern light.

Silver:

Where you take him: Bookstore date

Whether a big chain store or a cute local owned place, the idea is the same. First, you both find the cheesiest romance novel cover in the store. Next, you checked out the cook books, looking for the weirdest and worst sounding recipes (you joke about getting it for Lilia then laugh at the glare he gives you). Finally, you both choose a book for the other that you’ll read then reconvene to talk about at your next date. You find him an adventure book, something you would have called epic fantasy back in your world. He gets you a collection of well known fables and myths from across Twisted Wonderland. He’s slightly worried that you’ll be insulted in his reference to your lack of cultural knowledge of your new world, but you love it, especially the gorgeous illustrations for each story.

Where he takes you: Horse riding along the beach

This can go one of two ways, depending if you know how to ride a horse/are comfortable around them. If you know how to ride, Silver will borrow someone’s horse from the equestrian club for you to ride. If not, you’ll ride behind him, arms hugged around his middle as you cuddle close. Either way, you’ll ride down to one of the beaches along Sage’s Island. You’ll ride along the beach, darting in and out of the waves. Silver will probably have packed a small picnic that you can eat while watching the sunset. He ends up nodding off for a little while you take a break lounging on some dunes, but you kind of like him leaning on your shoulder like that.

Lillia:

Where you take him: Concert in the park

A few steps down from a full on festival, I’m imagining a lush green park, couples and families spread out on blankets, food trucks surrounding everything making the park smell amazing, maybe a couple of craft tents with knick-knacks for sale. There will be a large stage set up for the bands. Lilia prefers heavy metal, but I think he would like any show that plays something high energy. You’ll set up an umbrella to give you both some shade as you watch the acts. Lilia will regale you with tales of his travels and he’d probably love hearing about all the places in your world. At some point, you both definitely spend time dancing ridiculously. Lilia takes plenty of pictures to show off back at Disamonia.

Where he takes you: Esports competition

When Muscle Red told his online bestie Gloomamurai he was trying to come up with ideas for a date, the later said, “I got you,” and set him up with front row seats to the premier esports competition in all of Twisted Wonderland. Arriving at the indoor arena, you get a giant bucket of popcorn to share and Lilia buys you some merch of his favorite team. If you don’t know a ton about esports or the game they’re playing, Lilia will be more than happy to explain the rules to you. You’re surrounded in deafening cheers when your team makes a last minute score to win, hugging each other while jumping up and down. On the way back, Lilia promises to help you set up an account for the online game and teach you the ropes, while trying to remember to thank his friend when you kiss his cheek.

Malleus:

Where you take him: Mini-golfing

You can’t tell me it wouldn’t be adorable to see a giant Malleus hunched over a mini-golf club trying to gently tap the ball into a hole. I can see him at the first hole swinging like a normal golf course, sending the ball twinkling away, Team Rocket style. Mini-golf is a classic first date, and I think he would like the normality of it all. You’re not trying to super impress him, just treating him like a normal boyfriend, a normal date. And it gives you both more time to focus on each other, between desperately trying to hit the ball through the moving fan blades of the windmill hole.

Where he takes you: Historic castle ruins

I can imagine Malleus panicking at first about where to take you for your first official date. Does he bring you to a ball in the Briar Valley? A romantic opera in perfect box seats? Do you start picking out your engagement rings? Instead, he finally decided on an old reliable choice, harking back to how you both first started bonding in the first place. He finds beautiful old ruins, either in Briar Valley or somewhere else, and you just stroll and talk. He’ll tell you about the architecture, maybe the history of the location, pointing out whatever interesting gargoyles he spots. You both understand you don’t need grand gestures or impressive and expensive dates. You’re both happiest being with each other.

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