"Alright Cupid, you've agreed to help. So no matter how much you want to not do this, you can't back out helping Dexter."

Cupid was mumbling to herself as she left her crownculus class. Crownculus was Cupid's least favourite class. It wasn't that she was bad at the class, on the contrary she was doing really well, it just didn't agree with her personal philosophy. Not everything can be solved with an equation. Love cannot work that way. You can guide it, but no equation can show you what your heart wants. This class just added on to her already miserable mood.

Just yesterday Cupid was given detention for a month. She now has to complete her detention in the library. If that wasn't the caramel on top of the apple Cupid agreed to help her crush, Dexter Charming, get a date with Raven Queen. It kept Cupid up all night, replaying the same scene over and over again. Needless to say Cupid was not in the best of moods.

Cupids state of mind started to improve as she made her way to the cafeteria for lunch. Just a moment in her day to just relax and enjoy a good meal. Luckily for Cupid, they were serving one of her favourite meals; spaghetti. This simple pasta dish brought a smile to Cupids face as she remembered her dad telling stories of all the couples he brought together through this meal. Out of the sauces available, Cupid chooses the one filled with spices to give that extra kick, along with a nice, crispy garlic toast. After paying for the meal, Cupid heads over to the salad bar, garnishing the pasta with parmesan cheese and making a greek salad to complete her lunch for the day.

Turning away from the salad bar Cupid makes her way through the cafeteria, looking for any of her friends to sit with. She didn't have to look for long as Cupid found a small group just down the stairs. The first to notice Cupid was Cedar Wood. Cedar waved to Cupid, capturing the attention of the other girls at the table. Sitting with Cedar was Cerise Hood, Ashlynn Ella, Hunter Huntsman and, with a spot open right next to her, Raven Queen. Cupid places her tray on the table and sits down next to Raven.

Cupid held no negative feelings towards Raven. In fact they were great friends. It wasn't Raven's fault that Dexter had a crush on her. Love is unpredictable that way. You can't help with who you fall in love with, and Cupid was grade A material for that.

"Hey guys. What's new?" Cupid asked happily.

"Just talking about Ashlynn's new clothing line idea." answered Cedar.

"Oh hexcellent! Are we having another one of your secret fashion shows?"

Ashlynn shrugged her shoulders before responding to Cupid. "I don't know. I still have to design and create the clothing. Then find a suitable place to have the show where Grimm won't find it and my step-sisters don't take over it like last time."

"Though it was pretty funny to see them in rags and cleaning the whole cafeteria after." Raven chimed in.

Everyone at the table couldn't help but laugh at the memory. Cerise was the first to recover as she continued to eat her turkey sandwich. After a couple of bites, her attention is focused on Cupid just as the last fits of giggles stopped.

"Speaking of Ashlynn's step-sisters, I heard you got stuck helping out the Evil Step-Librarians for detention. How's that story going for ya?"

'Oh, you know, the same old drill. Never getting a single word from them besides the usual 'Quiet in the library.' I at least get to work away from them." Cupid said, taking a bite from her salad.

"What do you have to do?" Raven inquired.

Cupid swallowed her food. "I got to clean out the left wing. Just the usual dusting of the shelves and arranging the books back in order." Cupid explained. "It's not all bad. I do have some help."

Hunter raised his right eyebrow. "Who else has detention with you?"

Cupid shook her head. "No one. I get help from the Evil Step-Librarian's assistant."

"That has got to be horrible." Cedar said, sticking her tongue out in disgust. "Who would ever want to willingly work for those two?"

Cupid couldn't help but giggle, having the same though just the other day.

"Funny you should mention that. It turns out it's actually-"

"Hey guys."

Everyone turned to see Dexter coming by the table, waving his hand shyly at Raven. Cupid swore that her heart missed a beat as Dexter came closer to the table. Cupid was hoping Dexter would sit beside her for lunch; alas her dream was crushed when she saw him with an empty tray, notifying her that he was already done lunch. While everybody said hello to Dexter, Cupid was still lovingly staring at Dexter. Thankfully she caught herself and said a quick 'hi' before anyone noticed, a faint blush appearing on her pale complexion. Dexter, having accepted the greeting, turned towards Raven.

"Hey Ra-Raven. You're looking gort- I mean great! You're looking great! I don't even know what gort means. Though if it does mean something good than you are totally gort. Why am I still talking?" Dexter uttered, slowly fumbling over his words and speaking fast due to nervousness. Cupid took notice of that.

Cupid didn't understand why Dexter was so nervous. It would seem she would have to get to the source of that problem to actually help Dexter. Plans were gradually forming in Cupid's mind on how to help Dexter. Cupid was so preoccupied that she almost missed Raven replying back.

Raven let out a small laugh. "Thanks Dex."

"So where you off to now?" Hunter asked.

"Off to hero training." Dexter answered, losing his nervousness. He turns to leave but turns back to the group. "Spell you later Cupid."

Cupid nods her head happily. As soon as Dexter leaves, all heads turn to Cupid.

"So Cupid, why are you seeing Dexter later?" Ashlynn asks in a curious tone. All the other girls chimed in, interested in knowing what was between Dexter and Cupid.

"Remember how I said the Evil Step-Librarian's assistant was helping me during my detention?"

Everyone nodded, urging Cupid to continue with her answer.

"Well the assistant is Dexter. I'll see him this evening once school is done."

Cerise snorted at the thought of Dexter working under the Evil Step-Librarians. "Dexter must love it." Cerise said, her voice laced with thick sarcasm.

"Well I don't think he had much of a choice." Cupid added. "Dexter is working at the library because his parents asked him too. You all know how he wants to impress his family, especially his father."

Murmurs of agreement went around the table. Dexter's dad always did seem to favour Daring. Dexter would most likely do anything to get his father to praise him. The conversation gently teetered away from Dexter and Cupid's meet up. This allowed Cupid to not have to fully focus on the topic at hand. Instead she was quietly eating her meal, her mind thinking about how to help Dexter later today; even if it was hurting her heart.

The rest of the day went by smoothly for Cupid. As the last class bell rang for the day, Cupid was already on her way to the library. She knew where to go so as to not repeat what happened yesterday, Cupid just walked by the Evil Step-Librarians. They didn't take much notice of Cupid, only looking up once to acknowledge the fact she was on time for her detention. Upon arriving in the left wing, Cupid placed her possessions on the table and started to take books down to start dusting. Waiting patiently for Dexter Cupid knew exactly what the first thing she needed to do to help. Having only taken the first row of books down, Cupid heard footsteps coming into the room. She turns her body to see Dexter entering the room.

"Hey Cupid." Dexter said.

"So you can arrive on time." Cupid jokingly said. "And here I thought I would have to wait an hour before you arrived."

"Haha very funny." Dexter said with a smile forming at the corner of his mouth. He knew Cupid was just teasing him so he decided to play along. "I thought I would be catching you again but it seems you learned your lesson on being in high places."

Both teens tried to keep a straight face but both couldn't hold and started to laugh together. Cupid continued to laugh as she went back to work, Dexter joining in soon after to arrange the books in proper order. As they started to get into the groove of things Dexter couldn't wait anymore.

"So Cupid what is your plan in helping me ask Raven out?"

As dexter's back was turned away from Cupid, he didn't see the slightest of pauses from Cupid. With a deep breath Cupid continued collecting books before answering.

"Well I thought I'd help you slowly throughout the month. Each day a new lesson on what to do or what you should improve on. Think of it like a class. New material each day with asking Raven out as the final exam."

Cupid's voice was neutral, every ounce of focus not to sound sad. Dexter was thinking over Cupid's plan. He liked the thought of preparing for the moment he always wanted since entering Ever After that year.

"That sounds really good Cupid. What is today's first lesson?"

"...Working on your nervousness around Raven."

Dexter had to fully stop what he was doing. He was not expecting that to be the first lesson. Cupid noticed the halt in his work, deciding to continue talking.

"You were completely fine around everyone else at the table, even me." Cupid started to explain. "It wasn't until you got to Raven that you started to slip up. Thinking about it you are shy around everyone at school except for a few of your friends. What I don't understand is why you are? There's no reason for you to be."

Dexter gave out a soft sigh. "I can't help it. I have great expectations to carry and I'm afraid to mess up. I may not know my full destiny but it's supposed to be big. If I was more like my brother, the great Daring Charming, my life would be so much better."

As soon as Dexter finished his last sentence a light bulb went off in Cupid's head.

"That's it! That's the reason behind your nervousness!" Cupid said, smiling brightly.

Dexter had a perplexed look on his face as he stared at Cupid. "What's the reason?"

"You comparing yourself to your brother. That's what's making you so shy. Dex…you can't contrast yourself with your brother. You and Daring may be brothers but you two are different from each other. Daring is Daring and Dexter is Dexter."

"But I'm nothing special! Daring gets all the attention and praise. Why shouldn't I aspire to be more like him?"

Cupid gave Dexter a cold hard stare that made him flinch.

"First off."

WHAP! Cupid slapped Dexter hard across the face. Dexter didn't move from his spot but he was stunned at what happened, a clear red hand mark appearing on his right cheek.

"I don't ever want to hear you say you're nothing special! You are great and special in your own way. Those are the areas we have to work with. I've seen you when you're being yourself. Your calm and composed, knowing what to do or what to say. I'm stunned sometimes when I see you like that because that's the Dexter I fell in lo...luck with to know as a friend!"

Dexter looked down in shame as Cupid finished her small rant. Realization dawned on him; Cupid was right. He was so caught up in becoming more like Daring that he was afraid. Afraid of not getting any praise or not filling in the shoes of his father.

"...You're right Cupid. I've been so focused on being someone I'm not."

Cupid gave Dexter a smile as he brought his head up. "As long as you know, we can start to fix it."

"...What do you suggest we do?"

"For now we look at your strengths and weaknesses and go from there."

"That sounds good." Dexter said before going up to Cupid and giving her a hug.

Not one to deny a hug from her crush, Cupid hugged back.

"Not that I'm complaining but why the hug?" Cupid asked as Dexter ended the hug.

"For being a great friend."

The comment took a stab at Cupid's heart, but she smiled nonetheless. Her attention was soon focused on the disappearing mark on Dexter's face. She rubbed the back of her head sheepishly.

"Sorry about the slap. Looks like I hit too hard."

Dexter shook his head. "Don't be. I needed it. With your help I can get out of this shell I created."

"Alright then. Let's begin in knowing the real Dexter."

That's right another chapter up. I was so happy with the way the chapter turned out.

Some things to talk about. First off I'm gonna try and make each chapter represent a day. For the full month of detention I'm hoping to get 30 chapters for this story. So for this I'll ask some questions on certain chapters. Questions like what the next lesson should be for Cupid to teach Dexter. No question for this chapter.

Second, I feel like I made Cupid and Dexter a bit occ near the end. You know with the slap and everything. Let me know in the comments how you felt about it.

Thanks for the great reviews and support. This will be a great story in my mind.

Until next chapter,

Morantis

*Looking at my work I noticed a really big mistake. When Cupid told Dexter what her lesson was I wrote Cupid when I should have written Raven. Sorry for this mistake. Hopefully the next update will be an actual chapter, not fixing my mistakes.