Disclaimer: I don't own Trapped in A Dating Sim: The World of Otome Games Is Tough For Mobs.

Julius Pov

As crown prince I was granted an office by the academy a privilege usually only afforded to each year's representatrive. Normally it would be nothing but an inconvenience that would enable the nobles who only saw me for my title to hound me but now it would serve as an excellent place to meet with Leon and Angelica. As I waited with Jilk and Greg for them to arrive I thought about the girl who'd slapped me shortly after Leon's speech.

" Marie Fou Lafan." I smiled softly as I whispered her name under my breath. Her refusal to apologize after slapping me for my rudeness was a breath of fresh air compared to all of the other noble ladies, which was why I had plans to meet up with her after passing the task of looking after the scholarship student to Leon and Angelica. With this time consuming task Angelica wouldn't have time to bother me with lectures about propriety and I'd be free to interact with whoever I chose to, already she'd been bugging me about the tea parties that make students were expected to host ignoring my desire to have mine be a small affair because it wouldn't be suitable for someone of my status. I pitied my future replacement as once he became prince she'd inevitably try become his queen. Perhaps Jilk or Brad might be able to suggest some suitable candidates for Leon's future bride.

!!! Knock knock knock!!!

" Come in." I said the knocking having jolted me from my musings. I watched as the door opened to admit Chris and Leon. The latter of the two looking rather irritated. " Ah Leon how good of you to come."

" Your Highness." Leon greeted me with an overly polite tone as he bowed, almost as if he knew how much being addressed by my title annoyed me and did it on purpose.

" Please call me Julius." I said before continuing. " We're just waiting on one more person and then I'll explain why I had you brought here."

As I finished speaking the door opened and Angelica walked in followed by Brad.

Leon pov

Chris coming up to me and telling me the prince wanted to see me was a surprise. The prince trying to be friendly with me was another surprise and one I wasn't happy with, but perhaps even more surprising was the arrival of the villainess given that I was certain their relationship was strained in the game even at this point in time.

" Your Highness it is good to see you." The villainess said, her voice joyful and full of emotion even as she inadvertently continued to drive a wedge between her and the prince who's face briefly flashed with annoyance.

" Leon this is my fiance Angelica Rapha Redgrave. Angelica this is Leon Fou Bartfort." The prince said as he gestured at each of us when he said our names. That was admittedly helpful of him as now I wouldn't need to explain how I knew who she was even though we'd never met.

" Baron Bartfort I'm glad to finally meet you." The villainess said as she turned towards me and smiled warmly. Truly the game didn't do her justice in depicting just how emotive she was, even though she was being formal she sounded genuinely happy to meet me for some reason.

" Lady Redgrave the pleasure is all mine." I said bowing as was appropriate.

" Now I've asked both of you to meet me here because I was hoping to ask you two for a favor." The prince began speaking. " You see for the first time in the academy's history a commoner is taking part in the advanced classes on a scholarship. I was hoping the two of you might be willing to help her out as unfortunately I'm too busy to help Miss Olivia to the best of my abilities because of my duties."

While this was phrased as a request I knew I wasn't actually allowed to turn it down because of his position which led to the more important question. What the actual hell was going on ? The scholarship student he was talking about was obviously the protagonist but the prince shouldn't be passing this task on to me and the villainess, after all he was supposed to fall in love with her. Even if the protagonist wasn't on his route she still should've triggered the first flag by slapping him. So what had happened to lead to this?

" I figured that as an experienced adventurer Leon you would be able to help make sure she's able to pass her practical exams while Angelica can help her with the more theoretical stuff along with etiquette as being a commoner she probably doesn't know a lot of the rules." The prince explained in a way that sounded almost rehearsed. This whole plan seemed strangely well thought out and I couldn't figure out what the end goal was. The prince was going through a lot of work to involve me in things I wanted nothing to do with. I was supposed to be a background character not the protagonist's tutor.

" Your Highness while I don't wish to speak for the Baron I would be happy to help ..." The villainess began before trailing off clearly not knowing the protagonist's name. Great I probably shouldn't let the villainess and protagonist interact without some sort of buffer. That could go badly.

" I would be happy to help, your Highness." I said as formally as I could knowing he'd hate it especially after he'd invited me to call him by name earlier.

" Excellent, I'll let you two work out the details." The prince said before getting up to depart alongside Greg, Brad, Chris, and Jilk. " Feel free to continue using my office."

" Your Highness about your tea party? " The villainess kindly inquired. The prince ignored her as he and his friends left.

" Good bye your Highness." The villainess said looking crest fallen, she really did seem to love him for some reason, seeing that first hand instead of on a screen made her eventual fate seem even more terribly tragic.

" He hates that you know." I said before I could stop myself. I just felt bad for her so I'd at least do this and then nothing else. " Being addressed formally that is."

" It's how he deserves to be addressed. " Said the villainess with a surprising amount of conviction.

" Yeah but he seemingly can't stand it." I explained despite knowing I was likely screwing things up more than they already had been. " What he might deserve may not necessarily be what he wants though."

" An interesting perspective." The villainess said pensively. She looked like she was seriously considering advice from a mob like me.

" Anyhow we should probably figure out how we're going to help our new student." I said trying to change the subject. At this point I'd rather take my chances introducing the protagonist to the villainess and wait for them to hate each other than keep doing this.

" We'll have to introduce ourselves to her tomorrow." The villainess said. " I assume you'll handle adventuring lessons while I handle etiquette lessons we can split any academics between us."

" That works for me." I said noting how she seemed to get excited when mentioning adventuring, that was odd I don't remember her having a fondness for adventuring in the game. " Great we'll need to find somewhere where we won't be interrupted when we're tutoring her."

" I'll take care of that." The villainess said confidently, a beautiful smile formed on her face as she continued. " If it works for you we'll meet at the fountain tomorrow morning before classes."

" Alright I guess I'll see you tomorrow Ms. Redgrave." I said as I stood up.

" Angelica. If we're going to be working on this together you should use my name." The villainess said standing up.

" As you say Angelica, please call me Leon." I replied as we exited the prince's office.

" See you tomorrow Leon." Angeli- The villainess said as we parted ways.

" See you then, Angelica." I said heading towards my room. I needed to consult with Luxion, far too much had changed and I would need him to figure out why.

Author's Note:

So thank you to everyone who followed or favorites this story. I was frankly blown away by how many had done so in such a short amount of time.

This took a lot longer to write than I thought it would. Shockingly not because life got in the way but because I was trying to write Angelica's pov and couldn't quite find a balance between what we hear about her before meeting Olivia and what we actually see of her after meeting Olivia. We're told both by Julius and Stephanie that Angelica is cruel and Angelica doesn't really deny this. The issue is I don't want to completely discard those statements( despite them coming from unreliable sources) when trying to write her but can't really reconcile them with what we see of her character at least through light novels 1-3 (the ones I've actually read at this point.) and the anime. I imagine that after I have her interact with Olivia it'll be easier to write her and thus easier to write this.

On a separate note I want to address the pairing for this story since I got two comments suggesting that I don't do an Angelica/Julius pairing. I'll be honest and say that that specific pairing was never going to happen for a couple of reasons which I'll explain. The first of which being that I think the pairing is fundamentally broken in such a way that it can only make sense in a handful of scenarios. What do I mean by this? I think the pairing only works in the following scenarios.

Scenario 1 : Leon, Marie and Olivia all don't exist. This makes it so that Julius and Angelica enter what is probably an initially unhappy marriage where they(Julius) would gradually warm up to each other. Leon, Marie, and Olivia can't exist because any of them in theory prevents this from happening. If only Olivia exists we get the game routes or potentially even Olivia/Angelica since canon implies this is totally possible. If only Leon exists Angelica probably falls for him since they're ultimately more compatible than Julius/Angelica and he'd have to break his mob mentality because of the lack of a protagonist. Or we would get something like Iwasbored's Trapped On The Drawing Board chapter 2 where Julius would probably try to pick someone other than Angelica (because in his mind she's the worst option because he didn't choose her) and she'd retaliate like in that chapter. If Marie exists she would effortlessly get Julius to fall for her as seen in volumes 1-3 of the light novel and in the anime.

Scenario 2 : You fundamentally change either Julius or Angelica. This can be done a couple of ways. Either by turning one or both of them into an Si, or by altering their backstory in a substantial way likely years before canon. The later option is shown in chapter 12 of Iwasbored's story Trapped On The Drawing Board.

Scenario 3: Some sort of massive story change. So I know it sounds super generic but I'm talking like major extremes here. Like a real world Au or a post successful invasion of the kingdom or an apocalypse type story, etc. The type of story where they don't meet any of the love interests better suited for them until they're already solidly together or where everything is so chaotic that everyone is essentially a different character then they would otherwise be.

So because this story doesn't fall under those scenarios this won't be a Julius/Angelica pairing and I hope that I've explained my reasoning enough to not disappoint anyone too badly if they were hoping for that to be the endgame pairing. The endgame will probably be either Angelica/Leon or Angelica/Leon/Olivia.

Reader Response:

To Guest- Thank you. It means a lot to see excellent writing in a comment. Hopefully the above section explains my stance on the pairing. Already planning on it but thanks for the encouragement.

To Guest- Thanks. Hope it doesn't disappoint.

To Guest- Thanks. Hopefully it takes me less time to write the next chapter.

To Scott the Wanderer- Well he'll be sorta more cunning but I'm not sure exactly if he'll be less oblivious. Julius is an incredibly self centered and hypocritical character that obliviousness is kinda a core trait for him. My version of Julius will at least appear more cunning not because he's more intelligent but rather because he's more bitter than canon Julius, so it's highly focused cunning. Hopefully my above statements make my stance on the pairing clear. Your absolutely right on how Angelica would react to Julius' scheming. While the twist would be interesting it'd also unfortunately be totally unrealistic. Marrying someone to essentially a position is something I think wouldn't happen. Now the engagement only being valid if Julius was the crown prince might work a little better. The Fab five as you called them almost certainly will try to work together to help Leon and probably will succeed sometimes because you're absolutely right about Leon not being Leon without failing upwards.