Thank you to naaraanciiaa for your wonderful comment on the demons brothers' version of these headcanons, I'm so glad that you enjoyed them :)
And thank you for asking for a side characters version, I was goi to wait until I finished work today to write them, but I was eager to do it so I started them as soon as I replied to your comment while I had some ideas fresh in my mind.
I really hope I've been able to fulfil your request to you liking

I've technically uploaded two headcanon fics in one because I didn't want to exclude Luke but wasn't comfortable including him in the title "Falling For You", so I gave Luke his own title of "An Angel's Care" and wrote a similar but separate scenario to that of the brothers and other side characters, I really hope that this is okay.
I didn't include Mephistopheles, Raphael or Thirteen as I haven't been able to interact with any of them much yet, I'm sorry.

I'm sorry in advance for any mistakes within this work and I'll come back and correct them as soon as I can, but in the meantime I hope everyone can enjoy this work.
Thank you so much to everyone who has left comments, kudos, bookmarks or even read my works — I am grateful for your support :)

~K'rasu xx

Falling For You — Side Characters Version

For naaraanciiaa

You were making your way through the RAD corridor, barely aware of your surroundings as you spoke animatedly with him about your score on the recent seductive speechcraft test, when your foot caught on the stone floor and you felt yourself fall.

Lord Diavolo:
- "MC, look out!" Diavolo called out

- He saw you begin to stagger a few steps, but despite his warning you were still unable to correct your footing and began to fall forwards.

- You felt a strong arm sweep up your legs as another arm supported your back, within a split second you found yourself safely and securely scooped up in Diavolo's arms.

- Diavolo meets your gaze with a warm smile as he holds you close to his chest.

- "I wouldn't be much of a prince if I just stood by and let you fall now, would I?" He asks with a chuckle.

- He gently set you down on your feet before he offered his arm to you to hold onto, "will you allow me to escort you properly this time?"

Barbatos:
- Barbatos was so attentive in listening to you speak, that he foresaw your trip a little too late.

- He was about to warn you when you began to stumble forwards.

- You flinched and closed your eyes as you fell to the ground, but the impact of your fall never came.

- You instead felt yourself fall further than you should have before you landed softly in a pair of arms.

- You slowly opened your eyes to find Barbatos surveying you with a concerned expression.

- As you cast your eyes around yourself, you quickly note that there were two portals nearby — one was on the ground where you should have fell and the other was directly above your and Barbatos's heads.

- "It sounds like you're doing very well in your studies," Barbatos praised you, his worrisome expression softened into an encouraging smile as he spoke, "keep up the good work, MC."

Simeon:
- Simeon was just able to grab your hands and pull you up before you fell onto the floor.

- "Be careful now," he smiled kindly at you as he guided forwards a few steps to help you regain your balance and stoked the back of your hands with his thumbs in a reassuring manner, "you could've hurt yourself, are you okay?"

- He relaxed when you were steady on your feet again, but held your hand in his own as you continued to walk.

- Simeon became more aware of your surroundings, he was sure to keep an eye out for any more potential trip hazards — he gave your hand a gentle squeeze before he steered you away from them.

- He even made sure he slowed down to a pace that you were comfortable with.

Solomon:
- Solomon was caught off guard as you fell, but he was quick to react nonetheless.

- One second you were falling and the next you were frozen in mid air as though you were being suspended by invisible strings.

- Solomon let out an amused chuckle as he took a step closer to your body, placed an arm around your waist and used his free hand to interlock your fingers as he took your hand before he released the spell — letting you gently lean into his embrace.

- "You know, if you wanted me to hold you, you only had to ask." Solomon said playfully before he helped you regain your balance. "But I don't mind holding you this way either, it's not every day I get to be your knight in shining armour, after all."

An Angel's Care

For naaraanciiaa

As Simeon and Solomon were busy that day, you agreed to spend time at Purgatory Hall with Luke after RAD — he was excited to show you a new recipe he had learnt and invited you to take some cakes and treats back to the House of Lamentation for the brothers and yourself.

You stubbed your toes on the cobblestones of the Devildom street and felt yourself fall forwards, putting your arms out in front of you to break your fall.

Luke:
- "MC!" Luke yelped as he darted forwards and grabbed the hem of your RAD uniform jacket in an attempt to stop your fall, but the poor angel wasn't strong enough and you easily slipped out of his grip.

- He crouched down beside you as he watched you sit yourself upright on the ground and checked your stinging hands for any injuries.

- "I'm sorry, MC." Luke apologised with a frown. "If I was just a little bit stronger I could've stopped you from falling."

- You reassure Luke by telling him that he did his best and that you were grateful for his help.

- Luke helped you check your knees for any injuries, only to find that you had scraped and grazed them.

- "Hang on, I have just the thing!" Luke said as he began to rifle through his school bag until he finally pulled out a box full of colourful plasters. "I'll have you on the mend in no time," he beamed at you as he set about cleaning and covering your grazes.