A/N: A quick update! Hopefully I can keep this up until the end of July, but eh, no promises XD Thank you once again for your support, and here's the next one!

Disclaimer: I don't own Pokémon or the picture used as cover (though I did edit it).

Days

The day with the act

Cilan

Tuesday, December 3rd

"Ah, Cilan, please come in."

Mister Studee made a welcoming gesture, smiling jovially, and Cilan entered his boss's lavishly decorated office. Every time he came here there seemed to be more luxurious items added to the shelves, and while normally he wouldn't be bothered by his boss's overly extravagant style, now it only reminded him of his current mission.

"What brought you here today?" The jovial smile was still in place, but Cilan could read the calculation in his eyes.

Yes, what brought him here?

Well, he had plans, that's what. Cilan sat down in the chair opposite of his boss, smiling humbly. He was certain that Mister Studee could help him, but to attain that perfect result he had to balance the ingredients just right.

"Thank you for making time to speak to me, sir. I'm glad you were able to, on such a short notice," Cilan said.

The man's azure eyes narrowed just the slightest bit, though he smiled and nodded politely at Cilan's words. While Jack Studee could be very blunt at times, he also enjoyed subtle mind games, especially when some mystery was involved. It was distasteful, but Cilan would play along.

"As you know, sir, I love working as a Connoisseur, it is my greatest passion. And I also love my work as a Gym Leader and in the restaurant, but…" He hesitated intentionally. "But lately, it's getting progressively more difficult to combine the different jobs, especially with-" He cut himself off on purpose. "Anyway, I have come here for advice, sir."

He paused, as if in an attempt to gather himself. His deep breath to calm his fast-beating heart was no act, and Cilan had no problem putting a worried expression on his face.

It worked, though.

"Cilan, my lad, you aren't in trouble, are you?" Mister Studee had leaned forward, an expression of grandfatherly worry on his face.

"Oh no, sir, not trouble, it's not bad-" Cilan allowed a bit of a smile on his face, before looking worried again. "It's simply… some problems."

Mister Studee smiled in satisfaction at having caught on, and Cilan had to keep himself from smiling in a similar way for catching his boss's curiosity. If he spun his tale right…

"Hm, yes, well, what do you need advice for?"

Cilan looked down. "Well, sir, it is… I would not ask you, but it is of utmost importance… The League is too unbending to even consider my request, and I cannot ask my brothers..." The lump in his throat was real, and his hands had gotten sweaty.

It was make it or break it time.

"For personal reasons-" Which would stay personal. "-I would like to make more money. As I already work here, I was wondering if there are any possibilities for that."

It had come out a bit too rushed in his opinion, but the message was clear. The personal reasons were no lie. While Iris's enthusiastic reaction to the marriage proposal was a weight off his shoulders (and the memory never failed to make his heart soar, not even in this situation), it had posed a whole new set of problems.

The easier to solve but nonetheless pressing problem was their family. While Cilan had reassured Chili and Cress time and time again that things between Iris and him were alright after that fateful phone call, they hadn't given up in trying to find out what was going on. They didn't keep secrets between the three of them, and while Cress had been infinitely more subtle about questioning him, he had been just as relentless as Chili.

So, his brothers needed to know something soon, though Cilan expected no trouble from their reaction except maybe overenthusiasm. His parents would be delighted as well, and Iris didn't foresee any problems in telling her father and uncle. Then again, from the bits and pieces he had gathered, Cilan knew that Iris wasn't very close with either of her remaining family. Being sent off to boarding school had broken up things between her and her father, and her uncle was always on the travelling, though Iris loved seeing him on the rare visits.

What they would tell everyone was the point, though. They had agreed to wait with the announcement of the pregnancy until they had more certainty about the baby's health, but perhaps they were going to use a little white lie to make it seem they had been in a secret relationship for a longer time before marrying. Not that it would matter for long, since within a few months, Iris's pregnancy would be showing anyway.

Cilan glanced up at his boss, who still hadn't said anything and was frowning in thought. He didn't know if that was a good or a bad thing.

Finally the jovial smile returned, though Mister Studee's eyes remained cold. "Cilan, you're a good Connoisseur, but I can't give you a raise simply because you ask me, you know." He laughed, but the tone of warning in his voice was unmistakable.

"No, no, sir, I quite understand that, of course. Though it would have been a nice surprise if you had agreed to that," he half-joked. A raise had been his secret hope, but that was not what he had come here for. "I want to make more hours, or I wanted to know if there was perhaps another way in the Connoisseur's business to make more money..."

He knew there was, but it wasn't something one asked. It had to be offered.

Mister Studee's eyes glinted in recognition of what Cilan was getting at, and Cilan quickly glanced down at the table, waiting.

The family situation was not why he was here. That would be solved. Their living situation was a bit more difficult, with the distance between their homes, but that was also not why he was here. His Tropius was already very helpful, but if he managed to get a teleportation licensed Pokémon, that would be even better. But psychic Pokémon were rare and it was a bureaucratic and expensive mess to get an actual license.

It all came down to money. And even though Cilan had been in constant debate with himself whether he should do this and feeling appalled by himself for actually doing it, he knew it was the best solution.

And that was why he was now sitting here. Cilan carefully looked back up at his boss.

"You mentioned personal reasons." The heavyset man leaned forward a bit, all humor (fake or real) gone from his expression. "Do you have debts, Cilan?"

"No, sir, and I would like that to stay that way."

At that, Mister Studee's lips quirked a bit. Maybe he would be more empathic and helpful if Cilan revealed his real reasons, but Cilan would not speak about his engagement or Iris's pregnancy until he and Iris had agreed on what to tell others.

Mister Studee remained silent, as if waiting for Cilan to reveal just that, but he kept silent.

"So, no debts. Maybe an investment..." Mister Studee speculated, gauging Cilan's reaction. "An investment in the future... How old are you again, Cilan?"

"I turned twenty-five in October, sir," Cilan answered.

"Ah." The man nodded. "I was that age when I first married." A careful glance was thrown his way, and Cilan had to keep his face as neutral as possible. All Connoisseurs were extremely well in reading other people and that was both an advantage and a disadvantage when faced with a colleague.

"And I set up my own business not too long after that…" Mister Studee trailed off, still watching Cilan intently.

Silence stretched and Cilan wondered if he had made a mistake. He'd had to strike the perfect balance between amusing his boss with his act and not annoying him with too much mystery, and considering he wasn't willing to reveal his personal reasons the act had to be enough. Getting this job was a crucial ingredient for a successful future.

Cilan didn't look away from his boss's gaze, and finally, Mister Studee burst out laughing. "All right boy, then don't tell me. Personal reasons, hah."

Mister Studee sat up straighter, calming himself somewhat but still grinning brightly. "Fine, I trust you. I'm guessing you're trying to make more money for a house or marriage or perhaps a business of your own, though if you're planning on the latter I would advise you to spend a bit longer waiting around, get some more experience. Still, fine, I'll help you." His grin made place for a serious smile. "Alright, you can make more hours here, but that's not really what you were going for, is it?"

Cilan lost composure for a moment. He hadn't expected to be called out on his subtle hinting, but then again, he had known Mister Studee was blunt. He just didn't know if the man wanted more of the act or an actual honest answer.

"Ah, that'd- I mean to say, I wasn't- I didn't-"

Mister Studee burst out laughing again and Cilan felt himself flush. His boss liked to be entertained, so this was a good thing, though Cilan's pride rebelled at his behavior. Iris would never do something like this.

It was necessary, though.

"Very well," Mister Studee said, still smiling. "Then I would advise you to start working as a personal Connoisseur for some of our clients."

The victory didn't taste as sweet as he had expected, though Cilan smiled brightly. This was the best solution, even if it meant listening to rich and obnoxious people complain about their bought Pokémon and them not listening to his advice and being treated as a servant-

Alright, that was pessimistic and he should wait before making judgements. Certainly it couldn't be so bad.

"I would like that very much, sir, thank you."

His boss chuckled again and shook his head. "Ah, Cilan, you wouldn't, no need to lie to me, I know you too well. But you'll do it anyway, so that means you need money for something you really care about, otherwise you wouldn't go to such lengths. But if you really want to, I'll hook you up with some clients."

Mister Studee smiled again in that grandfatherly way, though Cilan couldn't say if he meant it or not. He supposed it didn't matter, he had gotten what he came for, after all.

He swallowed. "Thank you, sir, I would really appreciate that."

"Yes, that's more like it."

A/N: This was a bit of a more difficult chapter to write, but I hope it was understandable. Cilan's boss is quite complicated, and we might see more of him in the future. Thank you for reading, and reviews are always great!

Thank you!

Recommendations:

Pokémon: Sexual Tension and That's What She Said by Alyss Ashworth. FFN. Two very funny one-shots about Max trying to understand things about the adult world, such as what Brock means by sexual tension and what 'that's what she said' jokes mean. Featuring PokeShipping and ContestShipping :D Thanks to PokeshipperByHeart and anjumstar for the recommendation!

Pokémon: Uncomfortable by Apheleia. FFN. Thanks to anjumstar for recommending this to me! This is an amusing and cute one-shot about Gary and Leaf with an interesting theme. Very well written, and of course with a happy ending :)

Harry Potter: The Letter by Alohaemora. FFN. If you want to cry, you should read this. It's just… really sad. A well-written one-shot about Angelina dealing with the second of May, together with George and their children.

Recommendations are welcome!