One day at work, Gwen was finishing up her new cartoons for the paper and clocks out for the day. She leaves the Honeycomb Herald and to her surprise, Elder Kettle, the cups and the goat arrived to pick up Gwen.

"Hey guys! What brings you all by?"

"Hop on in girlfriend! We're having a day of fun!" Elder Kettle explained happily.

Gwen stood there, confused for a moment. But she shrugs it off, gets in the truck and Elder Kettle drives away.

They drive to the optician shop and to Gwen and the cup's shock, Elder Kettle asks the clerk for five expensive pairs of glasses and breaks out into song and dance. The screwdriver clerk is charmed and hands them the five pairs of sunglasses as Elder Kettle grabs the cups, human and goat and leave the shop.

"That was amazing! How did you know Chalice's song?" Cuphead asked.

"And how come you can charm Screwdriver Lady?" Mugman asked.

"And why are you acting like Ms. Chalice?" Gwen asked.

"You still haven't figured it out, have ya?" Elder Kettle asked.

Both cups and human look at each other.

"It's me, Chalice! I possessed your Elder Kettle! Day of fun!" Elder Kettle said.

Gwen's eyes widened, realizing Ms. Chalice possessed Elder Kettle.

"Wait a minute, why aren't your eyes glowing blue?" Gwen asked.

"I fixed that kink. Now you can't tell girlfriend!" Elder Kettle explained.

Mugman took a closer look and said,

"Banana oil."

"Nice try, Elder Kettle." Said Cuphead.

"Hmm, okay. Then, if I'm not Chalice, how would I know you two broke into a cookie factory and got thrown into the ol' Hooba Dooba? And how would I know you conned a snooty piano teacher and broke your ding-dong best friends out of the ol' Hooba Dooba?"

Gwen and the cup's eyes widened.

"Shh! Elder Kettle doesn't know we got thrown in the Ol' Hooba Dooba!" Cuphead whispered.

"Yeah. And Hooba Dooba's not even a thing." Mugman added.

"Wait a minute, Elder Kettle doesn't know I did those things." Gwen realized.

The trio gasped, realizing it was Ms. Chalice.

"It is Chalice!" The trio said at once.

Ms. Chalice in her ghost form appeared from Elder Kettle's mouth.

"Heya ding-dongs. Heya girlfriend!" Ms. Chalice said with a wink and went back into Elder Kettle.

The cups freak out along with the goat while Gwen stood there shocked.

"You're possessing Elder Kettle?" Mugman asked.

"That's right fellas. Day of fun!" Elder Kettle said.

"Wow, you really outdid yourself Chalice." Gwen complimented.

"Boy, oh boy!" Cuphead said excitedly.

"Not 'Boy, oh boy!' She took over Elder Kettle and didn't tell us! She's been playing us for fools all day!" Mugman argued.

"Would it be the first time guys?" Gwen pointed out.

"Well, now you know." Elder Kettle said.

"Huh. Well, I guess you're right." Mugman agreed.

"I guess I can't argue with that." Gwen added.

"Day of fun!" The group yelled and jumped in joy.

Suddenly, Elder Kettle's back threw out.

"Ooh! There goes Elder Kettle's bad back." Cuphead said as he helps Elder Kettle into the truck.

"So much for out day of fun." Mugman said sadly.

Ms. Chalice opens Elder Kettle's cap, pops out and says,

"We don't need Elder Kettle to have our day of fun."

"You mean, you can possess anyone?" Both cups asked excitedly.

Ms. Chalice exits Elder Kettle's body and said,

You bet your sweet striped straws!"

Ms. Chalice floats down and shapeshifted to her living form.

"Now goat, you watch Elder Kettle while we're gone, okay?" Cuphead asked the goat.

The goat bleated and Mugman said,

"Great! Let's go!"

"Day of fun!" Ms. Chalice said.

Both cups grab Gwen's hands and ran down the street.

"Woah! Guys! Slow down!" Gwen said as she was being pulled fast.

The four arrive at the Inkwell Pharmacy Soda Fountain and order four root beers.

Cuphead, Gwen and Mugman notice Ms. Chalice was gone.

"Hey, where did Chalice go?" Asked Cuphead.

"I don't know. She was here a second ago." Mugman answered.

Gwen shook her head as Cuphead started to get suspicious.

"Hmm. Well, I'm sure she won't mind if we start without her. Go ahead." Cuphead said.

Mugman declined and said,

"After you."

"Well, you always take the first sip. It's your thing, remember?" Cuphead asked loudly.

"Oh, of course. Mugsy remembers. And I'm Mugsy." Mugman chucked and started sipping.

"AH-HA!" Cuphead exclaimed.

"What?" Mugman asked.

"The real Mugsy always drinks his root beer floats in one gulp! Face it Mugsy, you're Chalice!"

"Chalice… get out of his body." Gwen warned.

"Alright, ya got me!" Mugman said.

Ms. Chalice exits Mugman's body and floated next to him as he has a brief headache.

"Oh, hey Chalice. Ooh! Root beer!" Mugman said.

The four raise their glasses, toasted and said

"Day of fun!"

They all drank their root beers until Mugman got a brain freeze.

"Ah! Brain freeze!" Mugman yelled.

"I told you not to drink it in one gulp Mugsy." Gwen said as she sipped.

Throughout the day, the four friends went around the Inkwell Isles for their day of fun. First they stop at the Fly Trap outside the window where Ms. Chalice possessed Ribby and started a pie fight as the four friends laugh. Next, they stop at Porkrind's Emporium where Ms. Chalice possesses Porkrind and tap dances though out the shop. Gwen and the cups laugh at Porkrind through the window as Jerry comes in and is pulled in by Porkrind, spins him around and dips him. Ms. Chalice exits Porkrinds body, as he drops Jerry to the floor and rejoins the group. Gwen falls back on the ground laughing at Porkrind.

At Inkwell Pier, they ride some rides until Ms. Chalice noticed Gwen's fellow theater classmates Sherman and his little girlfriend Doris at the 'Test your strength' game. Sherman swings the hammer, making the bell break at the top. As Sherman was about to give the giant teddy bear to Doris, Ms. Chalice possesses Sherman and makes him give the teddy bear to Mugman, to Doris's shock. Gwen takes the cups and leaves with Ms. Chalice exiting Sherman's body, only to have Doris whack his foot with the hammer in anger.

The four friends laugh as they walked, having the best day of fun together.

"Wow, this really was a day of fun." Cuphead said.

"You said it." Ms. Chalice said.

"I wonder what fun tomorrow will bring." Mugman wondered.

Gwen was now more curious about Ms. Chalice's ghost powers and decided to ask her about them.

"Hey, Chalice?" Gwen asked.

"Yeah girlfriend?" Ms. Chalice asked.

"There's something I've been thinking about." Gwen said, concerned.

"What is it?" Ms. Chalice asked.

"How did you get your…" Gwen was about to ask a question until Cuphead interrupted.

"Hey look! Let's get our fortunes and maybe we'll find out!" Cuphead said.

Gwen sighed as they approach four fortune-telling machines. They all pay and the machines make a noise and a card sticks out. Cuphead grabs his card and reads,

"'Your lack of common sense will be your undoing.' Huh. Well, that's no help. What about yours Mugsy?"

"Mine says: 'You're one tough cookie.' It's not a clue, but it's true." Mugman bragged and chuckled.

"What does yours say Gwen?" Cuphead asked.

Gwen took one look at her fortune and said cautiously,

"'Your ultimate test of love and friendship is coming.' I don't like this. It sounds scary."

"Eh, don't be too worried about it Gwen. Hey, what does yours say Chalice?" Cuphead asked.

Ms. Chalice looked at hers nervously, hides it and says,

"It's nothin'. It's just some silly nonsense." Ms. Chalice said nervously.

The cups and Gwen look at Ms. Chalice in confusion.

"Chalice? Is everything okay? You seem… scared of something." Gwen asked, now getting suspicious.

"Uh… Hey! You guys wanna get some cotton candy?" Ms. Chalice asked, changing the subject.

"Boy, do we!" Both cups said excitedly and both run off. Gwen walks after them hesitantly.

"Come on!" Cuphead called.

"You three go on ahead. I'll be right there." Ms. Chalice called.

Gwen decided to see what was going on with Ms. Chalice. She hides behind a tent, shapeshifts into a ghost, makes herself invisible and flies to Ms. Chalice. She notices her fortune card had a shape of the Devil's head with his evil eyes. Gwen's eyes widened, realizing the Devil is connected to Ms. Chalice somehow. Ms. Chalice goes behind a curtain into an alleyway with Gwen peeking over. Suddenly, the elevator appeared from the ground and Henchman opens the door.

"Uh, boss wants to see ya." Henchman said.

Ms. Chalice sighed and goes into the elevator.

"Yeah, I figured." Ms. Chalice said as Henchman closes the elevator door and disappear into the ground.

Gwen is horrified at what she saw, gasped and shapeshifts back into a human. She kneels down to the ground breathing heavily.

"No! It can't be! It can't be true!" Gwen said shakily to herself as tears were building up.

"What am I gonna tell the guys? The family?" Gwen asked herself and got up and exited the alleyway. She knew she had to tell her friends and family someway, somehow. Just then, the cups ran up to Gwen.

"Gweny! There you are! Where have you been?" Cuphead asked.

"Guys, we gotta talk…" Gwen was about to speak until Mugman interrupted.

"We were just gonna get cotton candy! Let's go!"

The cups grab her hands and pull her to the cotton candy line.

"Guys, I just learned something about Chalice." Gwen tried to speak again.

"I know, Chalice is a great friend!" Cuphead said.

"But guys!" Gwen protested.

"Yeah, she's one of us." Mugman added.

Gwen cringed at them still thinking she's their friend.

"Not exactly…" Gwen tried to speak.

"Gwen, what's come over you? You look like someone betrayed you or something." Mugman asked, concerned with Gwen.

Gwen cringed and yelled,

"I don't know!"

Both cups looked at Gwen in confusion. Gwen realized she shouted and said,

"Oh wow. That was loud. I'm sorry guys, I'm just concerned about Chalice." Gwen said after calming down.

"Eh, don't be too worried about her. She's our friend, she can handle herself." Cuphead assured her.

Gwen sighed, realizing if she told her friends about Ms. Chalice and the Devil, they won't believe her. She needed to find another way to show her friends the truth. After grabbing some cotton candy, Gwen takes the boys home back to the cottage.

"Looks like my only option is to learn about Ms. Chalice and her past." Gwen thought to herself.

Gwen looks in Elder Kettle's bookshelf and finds the book about the magic inkwell. Gwen goes upstairs to her room and closes the door. Gwen opens the book, looks through the pages until she spots a page about how to look into the past. She witnesses an eyeball being drawn and to request something or someone's past and the eyeball will spirit the user into a vision of the past.

Gwen sits on her bed, uses her ink pen to magically create the eyeball and catches it in her hand.

Gwen took a deep breath and said,

"Okay, I'm doing this. Looking into her past. I hope the guys are right and that she really is our friend."

Gwen held the eyeball and said,

"Show me Ms. Chalice's past and her connection with the Devil."

The eyeball glowed a bright light, floated and it's light blasted into Gwen's eyes, making Gwen's eyes glow bright. In Gwen's subconsciousness, she finds herself at an orphanage with four large anthropomorphic penguins caretakers forcing the orphans to work in harsh labor. Just then, Gwen finds a young Ms. Chalice being forced to work too. Gwen skips ahead into the past and sees that Ms. Chalice learned how to dance and have fun, making her get in trouble a lot. One day, Ms. Chalice escapes with her own glider she made and becomes a street urchin. Gwen witnesses Ms. Chalice learning to use her charm to get what she wanted to survive.

"Oh, my goodness! I had no idea she had it tough all her life! But how did Chalice get her ghost powers?" Gwen asked herself.

Gwen skips ahead to a few years later at Ms. Chalice's current age and singing, dancing and charming to get free stuff. Suddenly, she was accidentally hit by a street car and died.

"Chalice! No!" Gwen cried out. Suddenly everything went black.

Gwen finds herself in a somewhat familiar place. She saw that Ms. Chalice was a ghost.

"What happened? Where am I? I feel so strange." Ms. Chalice said as she discovered she was a ghost.

"I'm a g-g-g-g-ghost!" Ms. Chalice cried.

Suddenly, a spotlight shone on a desk and Henchman stood next to it. Gwen gasped at the sight and knew exactly who was sitting in the chair.

"That's right." The Devil said as he spun around to reveal himself.

"You're a g-g-g-g-ghost. I'm afraid it was just your time." The Devil said mockingly.

"What? My time? But that's not fair! Everything was finally coming up Chalice!" Ms. Chalice complained.

"File." The Devil ordered Henchman. Nothing happens.

"File!" The Devil yelled as he snapped his fingers.

"Oh!" Henchman said as he lifted up a huge file to the Devil.

"Yes, yes. Pity. Let's just take a look at your file, shall we?" The Devil asked as he made a pair of reading glasses appear on his face.

He opens it and takes a look and said,

"Ooh! What's this? Charming people into giving you things for free through song and dance."

Ms. Chalice chuckled nervously as Gwen said,

"Yeah, that's her thing."

"You know, I'm a bit of a song-and-dance man myself. Impressive, Ms. Chalice." The Devil complimented.

"It's just this little thing I do. Hey, listen, I really should be going." Ms. Chalice said and was about to leave. But suddenly, the Devil made flames surround her, preventing her from leaving.

"Stay a while, won't you? After all, how do you expect to dance without feet?" The Devil asked as he made his glasses and the flames disappear.

"So, I'm gonna be like this forever?" Ms. Chalice asked.

"Mm-hmm. Unless, you'd like to make a deal? I could offer you a second chance." The Devil offered.

"Oh, no." Gwen said worryingly.

"To be normal again?" Ms. Chalice asked.

"Well, you'd still be a ghost, but you'd have the ability to turn into your living form anytime you want.

"No!" Gwen exclaimed.

"Okay! Sure!" Ms. Chalice answered excitedly.

"There is one more thing. You'd owe me a favor to be named at a later date."

Gwen gasped in horror, realizing Ms. Chalice is actually in debt with the Devil.

The Devil reaches his hand out for a handshake and asked,

"Deal?"

"Deal!" Ms. Chalice said and both shake on it.

The Devil burns Ms. Chalice's hand, thus giving her the power to turn back into her living form. Ms. Chalice happily dances and shapeshifts from her ghost form then back to her living form.

"Hey! It works!" Ms. Chalice happily exclaimed.

"Of course. But don't forget, you owe me a favor." The Devil reminded her.

"Well, I best be hittin' the bricks." Ms. Chalice said as she was about to leave.

"Uh, uh, uh. Wallet!" The Devil scolded as he reached his hand out.

Gwen shook her head, knowing Chalice could snatch wallets without anyone noticing.

"Aw, you got me." Ms. Chalice said nervously as she hands back his wallet.

"Yes. I've got you." The Devil chuckled sinisterly.

Just then Ms. Chalice noticed next to the Devil's desk an open file that said the name 'Gwendolyn Mae Emmons' with a note that said 'human of personal interest'.

"Ooh, who's that girl on that file? And humans are real?" Ms. Chalice asked.

"She's nobody important, but the lucky human girl who carries and uses the magic inkwell I'm going to marry once I catch her. Only afterwards, I will obtain it's magic and powers through her."

"Huh, Birthdate: February 12…" Ms. Chalice read a little bit of the file until the Devil quickly shuts the file.

"Uh, uh, uh! No peeking into the files of others! It's rude!" The Devil scolded as he gave Gwen's file to Henchman.

Gwen realized in horror that Ms. Chalice knew about her all along and the magic inkwell. And that she lied about how she knew about the Devil seeking to marry her and how she knew her birthday and why she really gave her the amethyst brooch.

The Devil cackled and said,

"Okay, off you go." And snapped his fingers, making Ms. Chalice disappear.

Gwen suddenly disappeared back to where Ms. Chalice was hit. Ms. Chalice scared a crowd of people that surrounded her. Ms. Chalice celebrates her second chance at life and eats an apple from an apple stand until a bee police officer catches her and chases after her. Gwen watches the officer chase Ms. Chalice until she hides by the optician shop and runs inside, sings to the clerk and steals some sunglasses. Cuphead and Mugman pop out of the shop and follow her.

Gwen realized it was that very day the cups met Ms. Chalice and the events that led to the cookie factory incident. Gwen skips ahead a few days later and sees her 18-year-old self, following Ms. Chalice into an alleyway until the events that led her to con Ludwig and breaking her best friends out of jail.

Gwen skips ahead to later to the moment Ms. Chalice goes in the elevator. Gwen noticed Ms. Chalice reminiscing with a smile on her face. Gwen thought maybe she shouldn't jump to conclusions yet. She decided when she finds Ms. Chalice, she will have a conversation with her.

"Uh, okay, we're here. Good luck." Henchman said to Ms. Chalice as she gulped.

"Oh no." Gwen said worryingly.

Ms. Chalice stepped out of the elevator in Hell and nervously approached the Devil sitting on his throne as Gwen follows behind.

"Hey again Devil. Been a while. Say, you look fantastic. You seem to be getting younger and younger and younger." Ms. Chalice said nervously.

"Ms. Chalice, charming as always. Looks like you've been having quite a time up there. I see you made some friends." The Devil said with an evil grin.

"Yeah, just a couple of ding-dongs. You'd love them." Ms. Chalice said.

"And I couldn't help but notice you made a best friend with a certain… human girl?" The Devil asked sinisterly.

"Oh yeah, my girlfriend's like a big sister to me. I think you'd…" Ms. Chalice realized too late he knows about her friendship with Gwen.

"Oh wait, she's that human you're trying to marry." Ms. Chalice remembered.

"Yes. That's precisely what I'd like to speak to you about. It's time to cash in on that favor you owe me." The Devil explained evilly.

"Sure, what do you need?" Ms. Chalice asked nervously.

Gwen listened closely, feeling anxious and scared.

"I need you to betray…"

The Devil makes his magic mirror appear and showed a vision of the cups and Gwen walking home earlier.

"…The ding-dongs and your 'girlfriend'!" The Devil explained the favor.

Ms. Chalice gasped in horror. Gwen gasped in horror and realized the Devil plans to have Ms. Chalice betray her and the cups.

"No! No! Don't do it Chalice!" Gwen yelled as she knelt down in despair as everything around her froze in time. Gwen realized maybe it's not too late to stop it from happening.

"No wait, maybe I can stop this from happening. I'll find her and reason with her. Maybe I can help her get out of the debt. Save all four of us. Yeah, that's exactly what I'll do." Gwen said as she was giving herself some hope.

Suddenly, without warning, a familiar demonic voice called to Gwen,

"Uh, uh, uh! Someone's poking her nose where she shouldn't!"

Gwen looked around, but couldn't see the Devil anywhere as the visions around her started fading to black, realizing she was not alone anymore.

"No! You're not here! You can't be!" Gwen said in denial.

The Devil chuckled.

"My beautiful flower, I told you once and I'll tell you again. You can't escape from me, you never will."

Gwen started breathing heavily as she stood up looking around. She tries running away, trying to make her physical body wake up.

"Wake up! Wake up!" Gwen yelled, but to no avail.

Suddenly, everything around her started turning into fire. Gwen started coughing from the smoke. After coughing, she opened her eyes and finds herself in a familiar surrounding. Only a moment later realized she was in the palm of the Devil's hand, once again grew giant and looked down on her with an evil grin. Gwen ducked down and trembled in fear. The Devil chuckled and said,

"You poor little girl. I was hoping you'd never discover this power. But regardless, you did anyway. You just had to go seeking answers about your little friend Chalice, didn't you?" He said as he stroked her head like a pet.

"W-w-what do you mean you hoped I'd never discover this power? Looking in the past? I had a right to know! You took advantage of her! You're using her!" Gwen fearfully exclaimed.

"It's what I do, remember?" The Devil snickered.

"How did you find out what I was doing?!" Gwen demanded to know.

"Oh, a little birdie told me he caught a little glimpse of you snooping around in your ghost form at the Inkwell Pier earlier today." The Devil explained.

Gwen realized in horror Henchman was the one who caught her spying on Ms. Chalice earlier.

"What do you want?!" Gwen yelled.

"I'm very glad you asked. It's not polite to poke your nose into people's pasts. It's an invasion of privacy you know. I am very, very disappointed in you." The Devil expressed his disappointment.

"Like I care what you think?!" Gwen yelled.

"Because of your poking around into other people's pasts dear, I'm afraid dire consequences are coming your way… very soon." The Devil warned.

Gwen's heart started beating fast and grew more scared.

"No!" Gwen tried to deny his warning.

"The more you try to resist and reject me, the more dire the consequences become in the future. I will make sure of it." The Devil said in his demonic voice.

"No! Wake up! Wake up!" Gwen yelled as she tries to wake herself up again.

"Silly girl, I have taken control of your subconsciousness while you were snooping around the past. You'll wake up when I decide you'll wake up. I'm not finished with you yet." The Devil explained.

Gwen groaned and held her head in her hands in despair and started to cry.

"Oh, don't be sad my dear. If you don't want the consequences to become more severe, you will say nothing to your cup friends and your family about Ms. Chalice. And when the time comes, you will accept my marriage proposal and we'll seal the deal." The Devil explained as he tilted Gwen's chin up and gently wiped her tears.

He magically makes the same blue-diamond ring he tried bribing her with before appear in front of her floating as it is lowered into a ring box and disappeared.

"Got it my dear?" The Devil asked with a menacing grin.

Gwen looked sad and reluctantly nodded.

"Good girl. Now, where were we? Ah yes, you were about to wake up…"

The Devil said as he raised his hand and snapped his fingers, making Gwen disappear and waking up back into reality.

The lights from Gwen's eyes disappeared as she caught her breath, regaining control of her mind. Gwen breathed heavily and was sweating. Gwen is now torn with not speaking a word to her loved ones about Ms. Chalice and whatever consequence was coming and when. Gwen laid in bed, tearing up and tried to get some sleep. Then she heard the Devil's voice,

"Remember, we don't talk about Ms. Chalice…"

Gwen cringed as she yelled,

"Get out of my head! Leave me alone!"

After a while, Gwen finally calmed down and went to sleep, unsure what to do now. It was only a matter of time until it comes.