It happened at three in the morning (much to Itachi's despair). He was awoken by a black-haired demon.
Then he realized that it was Sasuke.
"Big Brother, you have a problem," Sasuke declared.
Itachi groaned and sat up. "Sasuke," he said sleepily, "it's three a.m. Whatever problem I have can be solved in the morning."
"It's technically morning," Sasuke said, "so get up!"
Realizing that he would not be getting any sleep until his so-called problem was solved, Itachi sighed.
"Fine," he said groggily, stretching. "I'm up. Now, what is this problem?"
"You're eighteen and you still don't have a girlfriend!"
Itachi choked. "What?"
And so begins Sasuke's search to find his precious elder brother a significant other (much to said elder brother's mortification).
Izumi Uchiha was minding her own business when someone knocked on her front door. Frowning slightly (it's five in the morning), Izumi opened the door, fully intending to lecture whoever it was about common decency.
Then she realized that the person on the other side of the door was Sasuke Uchiha. Unfortunately, Izumi figured it would be a bad idea to yell at the son of her Clan's head, especially considering the fact that the boy had never really liked her.
Sighing, she put on her best smile.
"It's nice to see you, Sasuke! Is there something you need?"
Both of them winced slightly at how obvious that was.
Sasuke, deciding to pity her, ignored it. "Ah, Izumi, I just had a question."
"What is it?"
"Are you single?"
Izumi pauses and, forgetting her manners, yelled, "WHAT THE HELL KIND OF QUESTION IS THAT?! BESIDES, YOU'RE WAY TOO YOUNG FOR ME!"
Sasuke blanched. "I'm not asking for me! I'm asking for my brother!"
Izumi calmed down slightly. She took a deep breath. "No, Sasuke," she said finally, "I am not single."
Sasuke looked crest-fallen. "Oh," he said.
Out of curiosity, Izumi asked, "Why'd you ask? Itachi didn't put you up to it, did he?"
"No," Sasuke said despondently. "I recently realized that Itachi would probably never ask a girl out himself, so I figured I would do it for him."
"Huh," Izumi said, "that's a rather pure-hearted goal."
"If he gets a girlfriend, then people will stop pestering me about girls!" Sasuke finished. "I mean, I get that Big Brother seems largely uninterested, but that doesn't mean that they can dump the whole 'produce an heir for the clan' thing on me!"
"...never mind," Izumi said, sweat-dropping.
"Out of curiosity, who's your boyfriend?"
"My fiancé, actually," Izumi corrected. "And I will not be telling you for fear that you will off him in the middle of the night."
"Why would I do that?"
"Why did you cry every time I held you as a baby? There are things about you that I have never figured out, Sasuke."
"...I'll take that as a compliment."
A few minutes after Sasuke left, Itachi Uchiha, a desperate look in his eyes, barged in. Izumi was having breakfast with her soon-to-be husband, who had just woken up.
She sighed and said, "What are you doing here, Itachi?"
Itachi, slightly startled (Izumi had always been pretty polite), said, "Did my little brother come here?"
"Yes, actually, he did," Izumi said.
"I am so sorry for anything he did or said. He will be making it up to you, mark my words...do you happen to know where he's gone?"
"I'm pretty sure that he mentioned Hana Inuzuka."
The blood drained from Itachi's face.
"Th-Thank you for telling me. I once again apologize for any discomfort Sasuke caused. I-I'll be going now."
With that, Itachi raced out the door.
Izumi's fiancé, who hadn't said anything up until then, asked, "Wasn't that Lord Fugaku's first son?"
"Yes, Yasahiro."
"He was chasing his brother?"
"Yes, Yasahiro."
"His brother was trying to get him a girlfriend, right?"
"Yes, Yasahiro."
"...I see."
Breakfast continued as usual.
Hana Inuzuka was feeding a sick squirrel when someone came into her office. Sasuke Uchiha, second son Fugaku Uchiha, walked in with an injured doe in his hands.
Being a vet was an odd job, but she never thought it would be this odd.
Deciding not to question it, Hana said, "Give her here."
Sasuke nodded. There was a tense silence. Then, Sasuke asked, "Are you single?"
Hana, not even looking up from her work, said, "Yes, and I intend to stay that way. Besides, I'm much too old for you."
"It's not for me!" Sasuke said indignantly. "I'm asking for my brother!"
"Your brother who has yet to show any romantic or sexual interest in anyone? Ever?"
"Yep."
"This pursuit of yours is definitely doomed to fail."
"Hey, I have hope!" Sasuke said.
"Well, you better hope luck is on your side, then."
"I am."
"...where did you find this deer?"
"You really don't want to know."
A few minutes later, a panting Itachi Uchiha walked in.
"Are you looking for your brother?"
"Yes."
"He mentioned an Anko Mitarashi."
Itachi winced. "Th-Thank you."
Hana nodded.
A few seconds later, a Nara ran in. "One of our sacred does are lost, do you-"
"Here," Hana said, carefully handing the baby deer with a wrapped leg to the Nara.
Itachi blinked. "Did Sasuke-"
"He did."
"...I see."
"...you're twelve," Anko said.
"I know!" Sasuke snapped.
"That's underage."
"I know!"
"...then why are you in a bar?"
"Because you're here."
"What, do you want me to train you?" Anko asked.
"Actually, I wanted to know if you were single."
The whole bar silenced. Anko raises an eyebrow, then chuckled.
"Hell yes!" Anko said. "I'm single! However, dating you is a little too close to pedophilia for my tastes. If you got a friend to recommend me to, though, I'm all for it. Preferably one that isn't underage."
Sasuke relaxed. Okay, she's single and ready to mingle. This is going well! "Actually I came here to set you up with someone."
"Really?" Anko asked. "Who?"
"My brother, Itachi Uchiha."
Anko slumped. "I've been trying to get with him for a while. He hates me."
"Oh," Sasuke said. "Never mind then."
Everyone in the bar grimaced in sympathy.
"Itachi~!" Anko sang.
"No," Itachi said emotionlessly. Anko sighed.
"If you're looking for your brother, he went to Ichiraku."
"Thank you."
"Sasuke?" Naruto asked. "It's six in the morning, what are you doing here?"
"What are you doing here?" Sasuke retorted to his teammate.
"Uh, I don't know how you haven't noticed by now but I'm kind of always here."
"...true," Sasuke conceded. "As for why I'm here...hello Ms. Ayame!"
Ayame looked up and blinked. "Hello Sasuke. You're Naruto's teammate, right?"
"Yes. I have a question for you, actually."
"What is it?" Ayame asked, humming.
"Are you single?"
Ayame went beet red and Naruto choked on his ramen. "E-Eh?!"
"Sorry if that was a little sudden, but I really do want to know..."
"Y-You're a bit young for me, don't you think..."
"Not for me, for my older brother! God, why does everyone think I want to go out with them?!"
"The way you said it very much implied that you were asking for yourself," Naruto said.
"Don't use big words, it scares me."
"YOU-"
"Yes," Ayame said, calming down, "I am single. However, I cannot date your brother."
"What? Why not?!" Sasuke demanded. He was getting very frustrated at this point.
"Because I like girls, not boys."
A look of incomprehension crossed Sasuke's face, followed by understanding. "Oh," Sasuke said, slumping in defeat. "Another no."
"Yeah," Ayame said. "However, I hope you find your brother a girlfriend!"
"Thank you," Sasuke muttered. "Well, I'll get going now."
"Hey Mr. Sasuke's Big Brother!"
"Hello Naruto," Itachi said, smiling slightly.
"Are you looking for Sasuke?" the woman behind the counter asked.
"Yes."
"Are you aware that your brother is trying to get you a girlfriend?"
"Yes, yes I am."
Ayame giggles slightly. "He had the funniest look on his face when he realized I was gay."
Something flickered in Itachi's eyes.
"Okay, who's next?" Sasuke asked himself. "Sakura and Ino are too young, Lady Tsume, while divorced, is too old (and scary), and Kurenai-sensei is dating Asuma-sensei."
After some intense thinking, Sasuke sighed. "Well, I guess it's time to start asking random people."
One Hour Later:
Sasuke's eye twitched. Apparently, word had gotten around that he was trying to find his brother a girlfriend.
Itachi's whole fan club was now begging that he set them up with him.
Sasuke's standards were low, but not that low.
"Sasuke?"
Sasuke blinked and turned around. "Shisui! Please save me!"
"Er...okay, but why is Itachi's fan club throwing themselves at you?"
"I was trying to get Itachi a girlfriend and they found out."
Shisui's smile twitched. "Oh. Did Itachi put you up to it?"
"No. In fact, he seemed pretty against the idea."
Shisui's smile twitched again.
"Shisui! Sasuke! What are you doing here?"
"Oh...hey Mother."
"Hello, Aunt Mikoto."
Mikoto frowned. "Neither if you answered my question."
"Itachi's fan club," was all Sasuke said.
Mikoto nodded and turned to the crowd. "Everyone, my son is currently not looking for a girlfriend but I'm sure that someday he-"
"STOP!" someone yelled.
Everyone turned. Ayame Ichiraku was hurriedly dragging a horrified Itachi while Naruto guarded them against the crowd.
When Ayame brought Itachi to the front, she faced the crowd and yelled, "ITACHI WILL NOT BE DATING ANY OF YOU, EVER! WHY? BECAUSE-"
"Ayame, please," Itachi begged.
Naruto grabbed Itachi's arm. "It must be done," he said.
"-BECAUSE ITACHI UCHIHA IS GAY!" She turned and faced Shisui. "AND HE IS IN LOVE WITH SHISUI UCHIHA!"
Complete silence. Then Sasuke demanded, "Why didn't you tell me?! I went to all that trouble for nothing!"
Everyone ignored him. Then, Mikoto quietly said, "You're gay, Itachi?"
Itachi winced then nodded.
"And you love Shisui?"
"Y-Yes."
Mikoto turned to a frozen Shisui. "Are you gay?"
Shisui coughed. "B-Bi, actually."
"Are you single?"
Shisui frowned. "Yes. Where are you going with this-"
Mikoto just wordlessly grabbed Shisui's arm and dragged him over to Itachi.
More silence. Suddenly-
"Now, kiss!" Mikoto demanded.
Both Itachi and Shisui went bright red. Before either could protest, though, Ayame pushed Itachi and Naruto shoved Shisui.
They fell to the ground. Their lips connected.
And suddenly the Itachi fan club became the ItaShi fan club as cheers rang through the air.
When the chaos died down, Sasuke cleared his throat. "Would now be a bad time to say that I'm Asexual?"
Mikoto was suddenly moping, depression lines hanging over her face.
"I'm never going to have grandbabies," she muttered.
Itachi sweat-dropped. "You know that I can still adopt, right?"
And Mikoto was grinning again. "That's why you're my favorite!"
"H-Hey!" Sasuke yelled.
"Though this does beg the question of who's going to be Clan Head after you, Itachi," Shisui said. "Neither you nor your brother is having biological children and the clan rules dictate the Head has to be part of the line..."
"We can worry about that later," Itachi said, going in for another kiss.
And that was the day that Mikoto finally felt accomplished as a yaoi fangirl.
Turns out that Fugaku didn't have any siblings. Neither did his father. Or his father. Or his father. Or his father. His father did but said sibling died without a wife or children.
After a lot of tracings of the Uchiha family tree, it was determined that when Izumi and her fiancé, Yasahiro, had a child, they would become the heir.
Itachi and Shisui got married five years after Izumi and Yasahiro. Also, thanks to a bunch of surprisingly strict and odd laws, Izumi and Yasahiro's daughter ended up being named Itachi's daughter on a few documents, though it was never really acted upon.
Ayame married Anko. It was quite an odd union, but it surprisingly worked. Naruto ended up being flower boy, much to the amusement of everyone involved.
Hana officiated a frankly alarming number of animal weddings (the most controversial of which was the union between Mr. Squirrel and Ms. Deer), but they were too adorable for her to care.
Finally, Sasuke ended up being the cool uncle to the two kids Itachi and Shisui adopted. And he never abandoned Konoha.
(Oh, and Orochimaru was eventually killed and eaten by a tribe in the wilderness of Grass Country whose snake dishes were considered the best on the continent)
The End