Naruto Uzumaki regretted not paying attention to Sakura's lecture on fashion back in the academy. He stared at the numerous shirts, pants, and other garments hanging on the store's shelf, hoping something stood out. Unfortunately, Ayame's rule of no orange prevented him from grabbing a 'wonderful' bright orange suit with matching orange loafers. Without a doubt, Sasuke would report such a transgression immediately to the ramen waitress and invite the holy wrath of the spoon.

None of the women behind the counter seemed interested in helping him find something presentable. Like most villagers, they viewed him as a pest that had to simply be ignored. Of course, their establishment always welcomed his money, but that was the extent of most merchants' hospitality. His initial idea of inviting Sakura ended when some crazy purple-haired lady chased him out of his teammate's house for accidentally letting out a bunch of mice meant for the snakes. Luckily, Sakura seemed to find the whole thing too funny and forgot to join in the chase. Unfortunately, the other two girls in his class, Ino and Hinata, declined his invitation. Ino, while finding it cute that he wanted to get dressed for a date, did not want people to assume that they were dating. Hinata fainted at the request, forcing him to flag down someone to take her back to the Hyūga compound. Poor girl must have been suffering from dehydration or something.

"This sucks." Naruto pushed aside a grey pair of pants before noticing the perfect outfit: a light blue suit with white fur cuffs. He grabbed it and went to the dressing room, unaware of the giggling women at the counter. He swapped his orange jumpsuit for the new suit and checked himself out in the mirror. "Looking good, Naruto!"

"Far from it. That suit makes you look like a porn actor." The deep voice startled the blond, who spun around to stare at the strange man leaning against the wall. He was an older man, probably in his fifties or sixties, with spiky red hair and a colorful red outfit. Naruto assumed he was a shinobi from the horned headband that said 'Oil.' "I didn't even know they still made suits in that color."

"Eh?" Naruto looked at the outfit with a massive grin. "It looks pretty cool to me."

"And you're the one who infamously wears bright orange." The man chuckled and shook his head. "Trust me, kid. You ain't going to impress a blind chick with that, let alone someone who can see."

Naruto rubbed his neck and looked down. "I guess you're right. This is a waste of time. I'll probably just ruin everything anyways."

The old man's face softened. "Chin up, young man. No need to be gloomy. Maybe I can give you a hand. Why are you looking for a suit?"

"I have a big date tomorrow night and nothing good to wear." He returned to the dressing room to change back. "This is like…super important! He expects me to look perfect, but she is also picky."

"Sounds like he knows what she really wants." The old man watched as a dejected Naruto flopped into one of the oversized chairs used by waiting customers. "Good thing you're looking at a master of romance."

"What? Master of Romance?" Naruto's sapphire eyes grew wide at the declaration. That was precisely what he needed. But unfortunately, without a dad to ask for help and the Hokage being busy, there was no one around to tell him how to woo Sasuke.

"Indeed, I am! The name is Jiraiya, famed lover and gentleman." The newly named Jiraiya struck a pose with a stupid grin that Naruto found cool. "This is your lucky day, kid. Allow me to prepare you for this date. With my teachings, she'll be putty in your hands." The Master of Romance marched back into the aisles of clothing with his new student close behind.

"When buying nice clothes, color and cut are the two most important factors to consider." Jiraiya dug through the racks. "I suggest sticking with neutral colors such as black, white, grey, or brown. Each one can give off a different vibe. Tell me about this young person you're dating."

Naruto avoided blushing at the thought. "Uh…she is pretty and formal. He takes a lot of things seriously and does not joke much. Kind of a bastard but in a cute way."

"Reminds me of my wife," Jiraiya remarked, thinking of a certain black-haired beauty in a positive light. "Anywho, given what you said, I'll suggest black and brown. Black symbolizes authority and strength. But, on the other hand, brown is the color of dependability, warmth, and wholesomeness."

The old man pulled out a black jacket, a white dress shirt, and a brown vest. "This looks good. Keep the jacket on during the initial dinner. Then, once you finish eating, you'll take it off to show off the vest."

Naruto memorized the instructions and rushed away to try on the outfit. It fit like a glove and gained a solid two thumbs up from the Master of Romance. Even the women at the counter looked at him with approval, their normal frowns replaced with respectable smiles. He purchased a black pair of dress shoes to complete the style. "Thanks a lot, Romance-Sensei! I'll knock her socks right off."

Jiraiya followed the young man out of the store, holding the bags. "Slow down, kid. Clothes are only part of a man. Looking good attracts the woman, but the conversation keeps her. Have you ever talked to a woman before?"

The blond tilted his head like a confused puppy. "I talk to Sakura all the time. Oh! Ayame is a girl too!"

"And, pray tell me, how do you talk to them?"

"Well…I'll talk about my training, ramen, or whatever book I'm reading." He grinned, believing himself to be smoother than glass.

"Right. Looks like I need to go over how to talk to a woman. Lead the way to your apartment, kid, so we can drop this stuff off." Naruto followed his teacher's instructions, guiding the old man back to the small apartment he called home. He pushed the front door open and cleared the ramen cups off the table.

Jiraiya wrinkled his nose at the place and frowned. "What a dump. Do you actually live here?"

"Shut up! This place is awesome." Naruto pouted at the insult to his home. "The Old Man says this is the best apartment in the unit." He chose to ignore the large rodent that ran across the counter. His next comeback died as Jiraiya's temper suddenly flared to dangerous levels.

"Who the hell told you such a stupid thing?" The Master of Romance glared at the cracks in the wall. Then, he noticed the worn-out cabinets and rusty sink currently used as a bathtub by a pair of relaxing rats. "How much money do you have in your bank account?"

"Eh?" Naruto scratched his head. "I have like…fifty thousand Ryo or something saved. Mostly from missions and the allowance from Old Man Hokage."

Jiraiya gawked at him as if too stupid to understand what had just been said. "Fifty…thousand? That's it? Impossible! We're going to the bank right now!"

"Bank?" Naruto once more looked confused and walked over to the bed. "I don't have a bank account. I just put all my money under my bed! Pretty clever, right?" The look on the old man's face grew more enraged. "Look, it sucks, okay? But this is the best place I was given. At least this apartment has running water."

Jiraiya's face softened immediately. "Well, don't you worry. I know far more than just romance. In fact, your life is about to get much better with me around." He flashed a cocky grin and did an odd little dance that Naruto wanted to emulate later when no one was watching. "Before that, we have to work on your conversation skills."

"How do we do that?"

"Since we don't have much time, I'll give you a crash course with a more in-depth lesson come later. But, first, since you are my student, you'll have to sign a special contract to symbolize your dedication to being a cool dude like myself." Jiraiya removed the large scroll from his back and rolled it onto the floor. "See? Even the Fourth Hokage studied under me!"

Naruto's eyes widened as he saw the signature of Minato Namikaze, his idol and hero. "No way! The Fourth Hokage studied how to be a master of romance under you?" He blinked as the hamster wheel in his brain spun. "If he was a Master of Romance, why did he die single?"

"Uh…well…he just ran out of time." Jiraiya did NOT want to go down that rabbit hole. "He died fighting the Nine-Tailed Fox saving all sorts of beautiful women in the process."

The mention of the fox made Naruto flinch. He still did not like to think about the demon living within his gut nor the fallout from the tragic death of the Fourth. While some of him hated that the Fourth picked him to be the fox's jailer, he knew that the Hokage must have had a particular reason to choose him.

"Where do I sign it?" Naruto reached for a bottle of sealing ink on his table.

"You won't be needing any of that," the old man chuckled. "Sign with blood! The path of being a cool dude is won through hard work, sweat, and blood!"

Without hesitation, Naruto bit his finger and signed his name beside his idol's signature. All Hokage must have been cool dudes, right?


Jiraiya stared at the ceiling of the hotel room. Sleep refused to come to him that night, and the thought of doing his usual nocturnal activities of drinking or visiting the sleaziest brothels in Konoha made him feel dirty. Memories of his greatest mistakes haunted his mind, forcing him to remember how he screwed up. Where did his long list of failures begin? His academy scores never got above a solid 'D' in most areas, and he was the last one of the Team Hiruzen to reach Chūnin. Tsunade's dislike of him, despite doing everything to be friendly, continued to bother him. The fate of the orphans from Ame always threatened to reduce him to a puddle of tears. Orochimaru still maintained the top spot, and Naruto's pitiful life was an extension of that.

The Toad-Sage slipped out from the covers and abandoned the warmth of his bed. Then, with a simple gesture, he summoned a black toad holding a shoebox. "Hate to bother you this late, Himitsu."

"Another late night?" The toad's soft, raspy voice held nothing but sorrow for her summoner. "This is the third time this week. Are you okay?"

"Peachy," he replied dryly. "Just been dealing with a lot of stuff." Jiraiya took the box from the toad, bowing deeply. "I'll keep this with me for the time being. Hate to keep bothering you."

Himitsu returned the bow. "You are never a bother, Lord Jiraiya. We of Myōboku worry for you." She hesitated for a few seconds. "Have you talked to Elder Fukasaku or Elder Shima about your feelings?"

"I don't want to concern them." He gave a weak smile. "I'll just be a bother."

"Very well, Lord Jiraiya." Himitsu gave a final bow. "You are one of us. They would love to have you visit soon." She disappeared in a puff of smoke.

Jiraiya retreated to his bed with the shoebox. He ran his hand over the numerous froggy stickers, remembering how Minato, as a child decorated the lid. His fingers pushed back the cover gently to deactivate the carefully placed seals. A part of him demanded that the box be thrown away to never make him remember the life that was and the life that could have been. Yet, the hero he dreamed of being gave him the courage to press forward despite the hurt.

Mementos of happier days filled the box, and the Toad-Sage couldn't help but smile. He took out a picture of Team Hiruzen, fresh out of the academy, and remembered how happy he was to be on the same team as Tsunade. Another photograph, taken sometime during the Chūnin exams that saw Orochimaru promoted, showed the entire team at a fancy restaurant along with Mito Uzumaki, older but ever regal. Everyone was looking at the camera but Orochimaru, who was staring directly at him with a smile that lacked cruelty.

In hindsight, it all made too much sense.

He dug through the numerous letters and certificates from his time as an active shinobi of the leaf. More photographs showing those early days of Team Hiruzen fell onto the bed around him. Soon enough, the photo of an albino-skinned woman with solid black hair caught his attention. A slight blush formed on his cheeks at the solid purple lingerie that barely covered her. She appeared in the following picture, cradling a large stomach and a prominent frown as he grabbed her breasts. It was one of the few times she actually threatened to slap him silly. Unlike Tsunade, who always resorted to violence, she never laid a hand upon him. However, she wasn't above threatening to knock some sense in him. They both knew she did not have the heart to do such things. Finally, he found a picture of a blond hair infant being held by him under the woman's watchful eyes. Finally, he took out a single golden ring formed of two serpents entwined in a loving embrace.

Hours passed. Jiraiya cycled through his favorite photographs repeatedly, imagining a world where neither fell so low and stayed together despite the world's harshness. How would Konoha have been if they had done their duties as parents and grandparents? Naruto would have had a much better life, without a doubt.

Resolve filled the Toad-Sage. For once in many years, he felt called to action. He removed a piece of paper from his notebook and began to write, not stopping until dawn's light poked in through the room's windows. His hand released the quill once satisfied with the words and came together with the other.

"Summoning Jutsu," he slammed his palms onto the floor and watched as Elder Shima appeared in a cloud of smoke. "Hey, ma'am. Hate to bother you this early in the morning?"

The little toad blinked, her yellow eyes widening in surprise. "Jiraiya-chan! I have been worried sick about you! Have you eaten today? I can prepare a big bowl of bugs just for you! Oh! Are you hungover? Swamp water clears up those nasty headaches in a jiffy!"

"Maybe later, ma'am." Jiraiya smiled at the dotting toad. He felt guilty for not visiting them more often. Maybe, he thought with a scrap of hope long dead, he'll bring Naruto to meet the Toad Elders. "I have an important message that only you can deliver. Got the time?"

"For you? Always." Shima took the letter from Jiraiya and read it over. "Oddly romantic…who is this going to?"

Jiraiya placed the golden ring on his finger and smiled. "My wife. Don't take 'no' for an answer. If she gives you any trouble, tell her that Tsunade has changed her mind about me and is lusting after me."

Naruto needed her. Sasuke needed her. He needed her. She needed them.


Sasuke took a deep breath and looked at herself in the mirror. It had taken her all morning to clean the house, prepare the first steps of the meal, and find a dress that Naruto would like. She admired the smooth orange fabric that clung to her willowy frame, trying to remember where she bought it. It must have been during the Wave Mission since the price tag was still dangling from one of the sleeves. Buying such a thing presented far too great of a risk when done in Konoha, and she remembered the thrill of being able to shop without fear of questions when arriving in the Land of Waves. Finally, with a deep breath and a final touch-up to the light makeup adorning her face, she felt pretty enough to present herself to Naruto.

She went into the kitchen to ensure the large pot of chicken stew was. But, unfortunately, her initial plan of making beef tongue ended when a certain Hyūga girl decided to visit unannounced to gather information about Naruto's date. Like always and with only a few things to hide, she told the truth that Naruto was romantically seeing a boy named 'Sasuke.' Heartbroken that her love swung for a different team, Hinata fainted, knocking over the delicate glass tray containing expensive tongue meat. It took her almost an hour to pick up the shards and summon someone to fetch the girl.

Chicken stew with fresh vegetables seemed like a safe alternative. Close enough to ramen in taste but with a rustic flare that her boyfriend would be unfamiliar with. A small giggle escaped her lips at the thought of Naruto being considered her boyfriend. The looks of despair on her fangirls' faces would be legendary. She allowed herself a few minutes of daydreaming before accepting the reality of the situation.

A sharp knock at the front door forced her to yelp. It was time.

Fear and doubt plagued each step she took. Thousands of questions caused thousands of hypothetical scenarios ranging from rejection to something far worse. She shook her head, reminding herself that this was Naruto Uzumaki, an innocent knucklehead with a heart far too pure for the world of shinobi. He would never hurt her. She needed to believe in him. Sasuke opened the door to the rest of her life with one final deep breath.

Naruto stood at the front porch in a neat, steam-pressed suit of neutral colors that complimented his bulk nicely. He held a single red rose along with a box of dark chocolates. His goofy grin, permanently plastered face whenever she was around, grew even larger upon seeing her.

"You look gorgeous." He extended both the rose and chocolates. "Thought I would get you something nice. The chocolates are imported all the way from Kumo. I got something with high…uh…cacao, so super dark chocolate!"

Sasuke accepted the gifts with a small smile. The blond seemed to remember her request to the fangirls about sweet items. She would enjoy these later with her stuffed fox and a barbarian movie. "Thank you, Naruto. You shouldn't have."

"Nonsense. I'm your boyfriend. Boyfriends got to get their sweethearts nice stuff, ya know?" Naruto rubbed the back of his head, a large blush threatening to consume his entire face.

"I'm your sweetheart?" She leaned forward with a smirk, forcing him to step back. "I shall gladly be your sweetheart, dope. Inside now. Dinner is almost made cooking." She led him to the kitchen and motioned for him to sit. "We'll have some chicken stew tonight and yeast rolls. I made plenty for your barbaric appetite and extra for you to take home."

Naruto sat at the table and watched as she placed a glass of water in front of him. "You didn't have to do all that work for me."

"Sweethearts have to make sure their boyfriends are well-fed," Sasuke smirked as her boyfriend melted into the chair. "I enjoy the new clothes."

He regained his composure quickly, eager to engage in pleasant conversation. "Thanks! Jiraiya-Sensei helped me pick them out."

"Jiraiya-Sensei?"

"Yeah! He is this cool old man who dances around and is a master of romance! We spent all day together yesterday talking about being a cool dude." Naruto downed the entire glass of water in a single enormous gulp. "He even talked about seals and training me as a ninja."

Sasuke stiffened as it dawned upon her who he was casually talking about. How the hell did her loveably stupid blond meet the legendary Toad-Sage? "Make sure to pay close attention to anything he teaches you. If this is the man I think he is, you'll be Hokage within a decade."

"Really?" Naruto jumped from his seat and rushed to her in a blur. She squeaked as he hugged her tightly. "I'll be the best Hokage! We'll move into the Hokage Mansion together!"

At least one of them dreamed of something pleasant.

"Careful making such promises to a girl," she softly chided. "She might get the wrong idea."

Naruto released her and returned to his seat, looking like a ball of sunshine. "It's a promise of a lifetime! Believe it!" Sasuke chose to keep back facing Naruto to avoid him, seeing the massive blush and tears rolling down her face. He did not need to worry about her crying over such a silly promise.

"I hope you can keep it," she whispered and stared into the strew. A comfortable silence fell upon the kitchen, and both soaked in the warmth of knowing that another person truly wanted them to be there. The timer for the rolls signaled that it was time to eat. Naruto helped set the silverware on the table while she prepared the bowls. Kakashi would have been proud of their teamwork.

She watched with white knuckles as Naruto poked at the stew with his spoon and prepared the first bite. This was the first time she had cooked something for anyone, and she wanted him to instantly fall in love with her…cooking. But unfortunately, her mother never bothered to teach her how to cook, believing that her…son…would be better off learning skills expected of a husband.

He stuck the spoon in his mouth and removed it slowly, ensuring all the broth and meat had been deposited. His face remained passive and analytical as if pondering the mysteries of the universe.

"Do you like it?" She prayed for a positive answer.

"It is better than ramen."

While she prayed for a positive answer, Sasuke did not expect a glowing, life-altering review. "Really?"

Naruto prepared another bite, grinning like a kitten full of milk. "Any food you make is better than ramen!" At that moment, Sasuke vowed to become a master chief just for him.


Another character is being called to the stage...who is the woman Jiraiya is married to and how does it connect to Orochimaru? I've put a lot of foreshadowing into this chapter, so i would love to hear some of your theories about what is coming. Hope you all enjoyed this chapter just as much I had writing it.

Just remember...All Hokage must have been cool dudes, right?