Chapter 1:

Tsunade sighed as she looked at the mountain of paperwork on her desk. It was going to be a long day, but it would be even longer since her trusty assistant Shizune was not there to help her. Shizune was in Suna for the month training medics on how to use a new sterilizing jutsu. This trip was important in maintaining the strong alliance between Suna and Konoha, but Tsunade found herself longing for Shizune's ability to nag her into her doing her work.

Some sake could help Tsunade relax and make the paperwork more bearable, but as Shizune pointed out many times, it was unprofessional to drink on the job. However, Shizune's absence was the reason for all of this incomplete paperwork. It had nothing to do with Tsunade's laziness. Any guilt Tsunade had about drinking dissolved, and she took out a sake bottle from her hidden stash under a false tile under her desk. What Shizune didn't know wouldn't hurt her. Tsunade finished off the bottle in record time; she was really stressed. Another bottle would surely be ok.

Just as the blond Hokage reached for a second bottle, the number one knucklehead ninja burst into her office yelling about something. She groaned and felt her blood pressure spike at the sight and sound of the blond brat.

"Naruto! What are you yammering about? I have tons of paperwork to do!" she bellowed.

Naruto crossed his arms and demanded, " Baa-chan! Make me a jonin!"

Tsunade laughed at his request. She knew this outburst was coming. She had promoted Sasuke to jonin last week, so she assumed Naruto was upset about having a lower rank than his rival.

"And why should I do that? Jonin are elite ninja that possess a high level of skill and professionalism."

"Well, I'm plenty skilled! I took out Pein, and I am totally professional! I have to put up with Sasuke and Kakashi all the time. It takes tons of professionalism to do that!" Naruto argued while flailing his arms.

"The fact that you're in my office demanding me to promote you says otherwise about your professionalism! " Tsunade fired back.

"Ugh baa-chan! Come on!" he whined.

Tsunade glanced at the clock on her desk and saw how little time she had left to do her paperwork. She needed to wrap this up quickly and get Naruto out of her office. Not to mention, her patience was wearing thin.

"Naruto, I have work to do, so get out of my office! I will think about promoting you once you show some more maturity."

Naruto sighed in defeat, but he suddenly perked up as he got an idea.

"Fine. Fine. I'll leave, but how about we make a bet?" he suggested with a mischievous grin. He knew that the Hokage loved to bet, so she wouldn't be able to resist his offer.

Thoroughly intrigued and somewhat intoxicated Tsunade inquired, "Hmm. What's your proposition?"

"I wanna bet that if I can get Sasuke and Sakura together within a month, you have to promote me to jonin."

The blond sannin paused and thought for a moment about his offer. She loved bets, but she also had a personal interest in this one. She wanted her dear student to find happiness, and it was high time for her to get some action. Additionally, that Uchiha brat might be less broody if he had Sakura. He could be a serious headache sometimes. Thus, she concluded that it was in her best interest to agree. Besides, she was already planning to promote Naruto next month, so he might as well do something good for her.

"Well, what do I get if you lose?" she asked.

"I'll do D-rank missions for a month!"

Tsunade chuckled. "Alright, we have a deal! Now scram before I change my mind!"

Naruto bolted out of the office with an elated grin and headed to his apartment. He was going to become a jonin and get his best friends together! He was a little surprised at how readily Tsunade had accepted his bet, but he suspected that it might have something to with her wanting Sasuke to be a little less moody and her apprentice to relax a bit. It was also common knowledge that the blond Hokage had a mild gambling problem. Walking down the streets of his beloved village, the blond nin was decidedly confident in his ability to win the bet with the legendary sucker.

Now that Naruto had been dating Hinata for over a year, he thought of himself as a relationship guru. In his eyes, he and Hinata had a perfect relationship. There was lots of laughter, romance, and commitment. They had never been in a fight, and every day together was a new adventure. Surely with his expert knowledge and experience of romance, he could get Sasuke and Sakura together.

As Naruto headed back to his apartment, he began plotting exactly how to get his two best friends together. He figured that he could get Sakura on board pretty easily because she obviously still had feelings for Sasuke even if she wouldn't verbally admit it. Officially, Sakura had long given up being a Sasuke fangirl in order to focus on her medical nin studies.

Although, Sakura blushed anytime Sasuke took his shirt off during training, and she was especially gentle when she healed him. Naruto never got that type of treatment from Sakura. Honestly, most of his injuries were from Sakura. She just didn't appreciate his pervy ninjutsu, as one ought to. Maybe, she would appreciate a Sasuke inspired pervy ninjutsu! That was an idea Naruto would definitely explore later.

Now, Naruto needed to find a way to get Sasuke interested in Sakura. If Sasuke pursued her, she would accept him. It was apparent that Sasuke cared for Sakura as close friend. He always protected her and reminded her to rest whenever she worked consecutive shifts at the hospital. While his interest in Sakura appeared to be strictly platonic, Sasuke wasn't close with any with females except for a few female relatives, so surely he had taken a special interest in Sakura. But how was he going to get the anti-social and practically asexual Uchiha interested in a girl in a month?

The blond jinchuriki groaned as he suddenly realized how difficult it was going to be to get his friends together. To him, they were an obvious match. Sakura could lighten up Sasuke and keep him in line while Sasuke could mellow Sakura out. The pink haired kunoichi had a tendency to get stressed out frequently due to her status as a jonin and head of the hospital. Sasuke also had a lot on his plate with missions, clan affairs, and the police station.

Honestly, both of them could use some romantic company to relax a bit. Sasuke would be less moody, and Sakura would yell at Naruto less. It seemed like a beneficial outcome for everyone – assuming his plan worked.

If his plan didn't work, Sakura would punch him into next week and Sasuke would chidori him. Not to mention, he would be stuck doing D-rank missions for a month! In hindsight, maybe he should have just bribed Tsunade with some sake. His pride would certainly take a hit if he had to take on such trivial missions for a month because Sasuke would never let him live it down. He had only been a jonin for a week, and he was constantly rubbing it in Naruto's face. Naruto shuddered at the thought of the plan going haywire. He really hoped that he could get his friends together without losing his pride or his limbs.

Reaching his apartment, Naruto headed straight to the kitchen. Plotting to get the most temperamental girl and the most anti-social guy in Konoha together was going to be an arduous challenge. Naruto couldn't work well on an empty stomach, so he dug into his leftovers from Ichiraku.

While he consumed his pork miso ramen, he decided to take the plan one step at a time. Romance took time. He didn't expect his friends to jump into bed together immediately. His first step would be to get Sasuke to Sakura as a woman, not just a teammate, before their upcoming escort mission next week. It would be a short mission to escort a daimyo's relative to a play in the Land of Spring. The mission would just be Naruto, Sasuke, and Sakura since Sai, Yamato, and Kakashi were all on other missions. It would be the perfect opportunity for Sasuke and Sakura to have some alone time. In order for them to take advantage of that time, they would need to be interested in each other. Naruto decided to commence the first part of his plan at tomorrow morning's training session. Giggling to himself, he mused that at least he was going to have an interesting month.