Prompt: Team Ro plays cupid

Ita/Saku Week 2021 🌸🍡


Uchiha Itachi had succeeded in becoming the new head of the Uchiha clan at 22 years old when he decided to retire from the ANBU corps.

He was told it was time to pick out a wife and he had no intentions of doing so, busy trying to advocate on the clan's interests, being isolated away from the rest of the village due to his father's one-sided way of thinking and going with past accusations, course it didn't help that he was blamed for the nine-tailed attack during the 4th reign.

Fugaku who was now at wit's end to make Itachi see the light, went to see the Hokage, who was currently, the 6th Hatake Kakashi who was highly amused by the state of things in the clan.

"Hokage-sama, is there a law you can enforce that entails Itachi to marry if he wants to keep being clan leader?" he asked miserably.

"Sorry Uchiha-san, but the Hokage's office cannot interfere in clan business unless it endangers the village and I'm pretty sure Itachi not marrying isn't going to hurt the village at the moment " he replied humorously.

Observing from the sidelines were of course Team Ro, the Hokage's personal 4 man squad of protection and surveillance around the tower.

Kakashi had appointed Yamato, and three younger members to watch over him. These members knew of Kakashi's old genin team 7, who were all now Jonin and 3 of the most powerful ninjas in the village.

Hmm, maybe they could help Itachi-san out finding a bride worthy of his attention?


Once Fugaku was gone, they appeared in a row at Kakashi's command.

"You heard everything, right?" he demanded

"Yes Rokudaime-sama" they replied mutely.

"I am technically not allowed to help Uchiha-san in my capacity as the Hokage but nothing says I can't help as Hatake Kakashi… I think it would benefit Itachi-san to visit the 'matchmaker? Hmm,' he suggested, smirking lightly.

Not quite as a direct command but he basically wanted them to help the Uchiha on his behalf as Kakashi-san.

Team Ro started their day individually, as someone had to be watching over the Hokage at all times in case anything happened.

They met every morning at 7 am to debrief when the Hokage arrived and met with their personal assistant to go over their day which lasted about 15 mins and then they would disburse and start their routine guard duty and watch.

Yamato who was captain and code name Sugi(Hardwood)

Uchiha Sasuke was assistant team captain and code name Tento(Lightning)

Hyuuga Neji whose code name was Supaisu(Spice)

And Uzumaki Naruto who was technically Hokage in training but needed at least 6 months experience of being an ANBU, mostly to learn hands-on experience in absolute stealth, assassination, high stakes intel gathering and negotiations. His code name was Kori(ice).

Naruto was forced to change his appearance for this assignment to the ANBU, his yellow spiky hair and orange clothes gave his identity away too easily so he temporarily dyed his hair brown, and wore darker clothing, with no hint of orange. When he wasn't on active duty, he could wash the dye out and it wouldn't give away his ANBU identity.

Kakashi also wanted him to expand his ninjutsu arsenal beyond his sage Jutsu, six sage paths, the tailed beasts, Kage Bunshin, wind afflicted Jutsu aka the many forms of Rasengan. Basically, any attack form that just screamed Uzumaki Naruto.

Of course, Naruto was a bit dumbfounded as all those things made him… him and without those, he didn't have much left. Which was exactly Kakashi's point. Sure he was probably one of the most powerful ninjas alive in their era but a Hokage should be trained in all facets of ninjutsu and have a large arsenal of attacks at their disposal.

He was recently learning to use water as his secondary nature after wind, and he also was learning to combine wind and water to make ice. It was like his wind nature training all over again.

"We have been given orders to "help" Itachi-san find a bride… discreetly. Any ideas?" asked Yamoto to the group. Neji looked bored and didn't say anything, Sasuke sighed as he thought his opinion shouldn't be counted for he was Itachi's younger brother and Naruto's eyes shined with glee.

"Has he tried blind dates already and he isn't planning on marrying a cousin?" looking towards Sasuke in mild disgust, the Uchiha liked to marry within the clan first, and not many had ventured out into the real world…

Sasuke glared back.

"Uchiha-sama wants to marry outside the clan if it was his choice. Of course, the elders disagree wholeheartedly with this so he has decided to not marry…"He explained awkwardly.

"Well, I don't think it would be hard to find a lady for they all seem to want one of your elite clansmen for their own" continued Naruto sourly.

"Hn" replied Sasuke refusing to say anything else on the matter.

Well, they weren't going to get any good ideas with just Naruto suggesting things. Yamato sighed.

"I think our first mission should be "guiding" Itachi-san to see the local Matchmaker."Yamoto decided.


Sakura debated if she should have taken on an ANBU assignment, like her two teammates, Sasuke was always going to want to be the best he could, minus becoming the Hokage, and Naruto was technically a genin still but with the upcoming appointment of his dreams, Kakashi forced him to be an elite ANBU for 6 months.

Sakura had decided to stay a Jonin and focus on her medical-nin duties to the village but that became quite routine since the end of the fourth war.

She had budding plans on creating a mental health institute for the younger generation but that was still in the works with Tsunade, Ino and Shizune.

She was pining over having a purpose since hers was fulfilled temporarily.

Being 17 now, she was just on the cusp of true adulthood and couldn't spend her nights like her older comrades, going out and enjoying the nightlife of Konoha.

Heck, she was even slightly jealous of Naruto for realizing and having mutual feelings for Hinata who had been chasing him since they were kids.

She had proven herself a capable kunoichi and was recently given a second chance at deciding who would take on the head of the Hyuuga family by pitting the sisters against each other in a 1vs1 match to see who was stronger.

Hinata had been distraught about it all week, not wanting to fight Hanabi a second time since their childhood and her being outcast as a true heiress given her being older.

She had actually demanded her father change how the clan decided its hierarchy. He only told her that if that is how she truly felt then she should succeed him as clan leader and make that change but it was out of his hands now that she was 17 and almost of age.

Naruto had gone over today at some point to cheer her up and give her tips on how to best Hanabi, having recently duelled her, as she was attempting to reach ANBU rank.

Love life shouldn't have mattered much being a kunoichi but Sakura saw how her friends were silently pairing up and she wasn't following down the same road, everyone expecting her to end up with Sasuke.

It was true she loved him when they were genin, but her feelings matured after all they went through and she didn't feel the same anymore. Sasuke never seemed to reciprocate her feelings so it was no loss to him. Besides, he was enjoying life before Itachi got married and his parents set their sights on him and his future as the clan leader's brother…

Currently, Sakura was lounging on her bedroom balcony at her parent's place, not deciding to get her own place yet. She had snuck a cider outside and was getting inhibited because she was that bored and mellowing about everything.

Suddenly a masked man appeared on her railing with a kitsune mask and black clock…

"Sakura, getting naughty with alcohol! I should report it to Hokage-sama" a familiar voice teased.

Swiping the mask off, it was clearly Naruto, well to her who knew him well. She had to adjust her view with the brown hair, concealed whisker marks, and green contacts that hid his bright blue eyes.

"They should get you a new mask, the fox makes you obvious even with your hair colour changed…." she commented throws it back at him grumbling.

"That's the trick though, it is obvious and even if they unmask me they can't tell its' me, still," he said, leering into her eyes deeply.

Blushing Sakura backed away before punching him lightly, casting him off her railing.

Laughing loudly, he disappeared as fast as he appeared.


Itachi was good at masking his true feelings and not being affected by others as he got older and matured fast for his age.

Mikoto had summoned him to her private dressing rooms as she skimmed over her collection of exquisite kimono that only the clan leader's wife owned.

"Itachi, who am I going to give this massive collection to if you don't get married?" she asked, trying to unruffle him.

"There are many women in this clan, mother… Perhaps we share the wealth around the other families?" he suggested knowing how she would react.

Her eyes narrowed and she stilled in her movements.

"Though I understand you are going to rid many of traditions in upcoming years, I do not believe it wise to cull the importance around your future wife's role in the entire clan. I don't wear these as symbolism to our wealth but more of a status of power and influence. Without a role model what will future Uchiha women aspire to uphold our good name?!" she demanded coldly, knowing he may not understand as well bring a son and not a daughter to the Uchiha.

"I'm sorry mother but my stance holds, now if you'll excuse me I have work to do" he dismissed himself leaving her to go back to his new office. That his father was just finishing vacating as he was now retired.

Sasuke arrived shortly after, still wearing his ANBU gear, and on active duty. He bowed to Itachi in respect, now that he was clan leader and not merely his older brother anymore.

"An encrypted message from the council of Elders and the Hokage… Uchiha-sama" Sasuke said, handing him the scroll.

Inside was a message that Konoha did not interfere in a clan's internal affairs but the Uchiha did hold one public transition ceremony of the new clan leader, especially if he was not engaged or married yet…

Itachi sighed, a formality he added to his list of things to purge as of him being the last Uchiha to do it.

In the era of the First Hokage, it was a tradition of all clans in the village to perform a matchmaking ceremony if the child taken over as the next leader was still without an incoming spouse to ensure the continuity of the clan, Traditional matchmakers looked to star signs and the arts to give the new clan leader signs of their match and by hosting marriage meetings, it would help determine a good match for marriage, most men were married within 3 months of this ceremony.

The only clan left in Konoha that still performed it was the Hyuuga...Itachi would perform it as it was last minute but he swore he would be the last Uchiha to do so.


Sasuke reported back to the group. Itachi was taking the bait, they didn't leave him any chance to deny the village probably one of their last matching ceremonies from times of old. The priestess that would perform it was turning 52 this year and there was no one else trained in the lost ways of the past.

Neji reported that the Hyuuga were on the verge of forgoing the tradition as well, if Hanabi succeeded they would perform it and if it was Hinata, she already had Naruto so there was no need, and perhaps they would forgo him as well if he was lucky.

This was their chance, only one needed to be close enough to overhear exactly what the priestess told him about his fate and how his sign aligned in the matters of love, course anything could interpret what she would say as any woman but maybe they would be enough to actually guide him to someone decent that he would reconsider and finally marry like his father so heartily wishes.


A week passed and the preparations for the Uchiha public ceremony at Senju Park, as typically would have been at the old Kikyo castle but it was destroyed in the Akatsuki invasion, just before the war.

Similarly to a wedding, the Priestess and important officials, the Hokage, Itachi's parents, the fire feudal lord, and elders stood on a makeshift platform on the end of the field and there were decorations, Uchiha banners and various shrine symbols aligning a lane that was created to go to the platform and on either side, the public was allowed to walk in and stand and witness this grand day.

Itachi was waiting for things to start in a nearby tent where he dressed formally in a kimono that was used for such events as these. Several cousins assisted him in dressing and would cue his entrance before joining the surrounding crowds.

He sat once ready for the signal to leave and walk down the aisle to the platform to begin.


Sakura, Ino, and Hinata were all off active duty and Hinata informed them that the new Uchiha clan leader, Itachi was going through the matchmaking ceremony of old in order to know what to look for in his future wife prospects.

"There hasn't been one of those since like our parents' time" commended Sakura, thinking back to which clans still had ridiculous traditions.

"My parents were the last to go through it because my father hadn't met her yet and was single, surprising the priestess described my mother perfectly and when they met months later, he just knew she was the one," Hinata commented thoughtfully.

"*snort*, there's no way to predict your future spouse, hence there is only one priestess remaining, it's a lost art because it wasn't always accurate," Ino said huffing

Sakura didn't contribute any more to their theories and complaints of such a bizarre thing that really old clans still did.

Gathering together with some of the others their age, they walked over to Senju Park to see the last official matchmaking ceremony of Konoha.

They got there just in time to hear the strings of a koto, and everyone grew silent, awaiting Itachi who appeared moments later, walking slowly down an aisle towards the people on the platform in the distance.

Itachi wore a formal kimono in navy blue, black and white, Uchiha fans adorning the back collar and on each side of his chest. His long hair was tied in a neat knot on top of his head, where he wore a small headpiece hat. The hakama was black and he wore white tabi socks with matching navy geta. Walking, he carried a paper fan of red.

Giggles and whispers surrounded them as Itachi's fan's and the woman of the village gushed at how handsome he was.

Sakura wasn't close enough to properly see every detail but she did think from the glimpse she saw that the Uchiha sure knew how to dress.

Itachi ascended the steps and bowed to the priestess. Everyone else took their seat on either side and sat on cushions as the ceremony began.

The Priestess wafted incense smoke over him and began a prayer.


Sasuke was assigned in getting the intel, as he was naturally seated next to his parents on Itachi's left and the closest person to them.

The priestess had awoken from her meditative session and began telling Itachi what he needed to know.

"You were born in the constellation of the twins and are destined for a woman who is stronger than yourself and wise enough to get beyond your stubbornness. She will have the soul of a ram and resemble a spring flower. You are polar opposites and she will help you do great things in the future Uchiha-sama" she told him.

Itachi disregarded the information, still intending to carry the clan on his own.

Sasuke cursed inside… for he knew exactly what the priestess was referring to.


The next day Sasuke reported to the others of Team Ro.

"So Tento, what did the old bat have to say about Uchiha Itachi's love life?" asked Naruto amused.

"Uchiha Itachi is destined to match well with Haruno Sakura…" Sasuke revealed.

A collective gasp from all of them that Sasuke was so sure.

"Backup Tento, what exactly did she say word for word," demanded Neji, already frustrated that he already interpreted it.

He repeated the verse from the ceremony and waited for the others to predict what it meant.

Yamato's eyes burrowed together for he understood how he could have thought of Sakura.

"What's Haruno-san's birthday?" asked Neji.

"March 28th" Naruto replied somberly.

"She fits like Tento says," Yamato confirmed.

"Tento… What about you?" Naruto asked seriously now.

The group looked between the two of them. Did Sasuke love Sakura?

"It was a childhood crush… we both don't feel the same anymore," he replied looking away.

Feeling a bit bad, Naruto put together their next move.


Team Ro decided that Sasuke would casually introduce the two of them at the upcoming end-of-summer village festival. From there, they would let nature take its course and report back to the Hokage on how their "cupid" mission went, hopefully, Itachi would like Sakura.

Sakura was very surprised when Sasuke invited her to go to the festival thinking that they were just going to meet up with Naruto and Kakashi and she agreed.

Sasuke treated her to a few stall games and treats before guiding her over to the gigantic tree in the middle of Senju park where Sakura noticed Itachi talking to the staff at the Hokage building. She lightly tugged Sasuke's sleeve indicating that they should interrupt them. Sasuke ignored her warning.

Walking up to the group, Sasuke bowed to Itachi and introduced Sakura.

Itachi internally cringed because he saw her resemblance immediately from his reading at last week's ceremony and gave a cold stare to Sasuke who stared back at him.

"It's nice to officially meet you again Uchiha-sama, Sasuke's told me a lot about you over the years, as we were on the same genin team I'm sure you're aware," Sakura said politely, wondering why Sasuke was forcing her to talk to his brother.

Appearing not to affect Itachi smiled genuinely at her before greeting her back, they eased into talking about Sasuke and Sakura's genin days with their teacher the Rokuadaime…

Sasuke slowly backed away from the duo once Itachi had then invited Sakura to his teahouse, which he frequented often after they were talking for quite a while. Sasuke excused himself, using Naruto as an excuse. Sakura gave him a curious stare as he was acting a bit weird but brushed it off before walking alongside Itachi to their destination.

Once getting to Naruto, who asked how it went.

The next morning Team Ro reported directly to Kakashi who was lounging amongst several scrolls.

"Status on the mission?" He prompted all business.

"We have disengaged from the target but set him up with his potential match" reported Neji.

'Kori?" Kakashi addressed Naruto.

"His match turns out to be Haruno Sakura-san," Naruto replied.

Kakashi chuckled as it was ironic.

"Good job Team Ro, please return to basic duties until I require your services next, dismissed." Kakashi commended them, waving at them dismissively.

They disbursed and were gone in a blink of an eye.


Itachi knew he should complain to the Hokage's office with intentional interference in Uchiha personal affairs… but he grudgingly agreed with their assessment. Sakura was very interested after speaking with her for the rest of the night at the teahouse; he even invited her on an official date on the weekend, which she accepted.

He did tell her about the ANBU's mission and she was enraged that they had been set up but they agreed to see where things went between them. Itachi was not informing his parents of the recent development… yet… they would be planning the wedding otherwise.


A/N: Happy Thursday, I can totally imagine Itachi being stubborn and not wanting to marry as the village would always be his first priority but of course he would get distracted by the lovely Sakura, Sasuke you sly man lol. As always feel free to review, comment, fav, follow, kudos, bookmark, fav, and like on either platform or both