Disclaimer: Don't own Naruto.
By the way this is a LONG chapter. Well compared to all the chapters I EVER wrote this is the longest. Hope you'll like it!
The next day Jiraiya was more calm and cool. Not too excited but he still got Tsunade flowers.

"Hello there Tsunade!" Jiraiya said coolly as he entered her room.

"You aren't going to ask me on another date again are you?" Tsunade asked seeing the roses. "Cause my answer hasn't changed!"

"Well it will now!"

"There is nothing you can say or do that will make me date you!"

"Oh get ready to change you mind cause I can say AND do something that will make you date me!"

"Oh yeah, what?" Tsunade sat back in her chair wanting to be entertained by what Jiraiya had to offer.

"Well you know all the money you owe?"

"Yeah what about it?"

"Well if you go on a date or two with me, we'll call it even."

"WHAT?!?! I- really- but- WHAT? You're kidding right?"

"Nope just a date or two. Think about it, pay 10,000¥ or go on a date or two with me?"

"I'd rather die a slow and painful death than to go on one small date with you!!!"

"Alright then, I expect my money by next week! Well unless you change your mind about the date."

Jiraiya started to SLOWLY walk towards the door.

"Jiraiya wait!" Tsunade stopped him.

"Yes, Tsunade?" He asked.

Tsunade sighed in defeat. "Alright I'll go on a date with you!!!"

Jiraiya jumped for joy and had a cheery grin on. He ran to Tsunade gave her the flowers, a hug and a kiss on her cheek and ran out in excitement and knew Tsunade was going to kill him for that.

After he left Tsunade was frozen with a small almost unnoticeable smile blushing and almost dreamy look in her eyes. She shook her head and sat down to continue her work but also continued blushing and looking at the roses.


Naruto got up and picked some more cherry blossom from the field and ran straight to Sakura who was at the KIA stone trying to see all the brave shinobi who pasted away.

"Oi, Sakura-chan!!!" Naruto said.

"Oh hello Naruto." Sakura greeted, she saw the flowers again. "Are you asking me out again?"

"Yup, will ya?"

"No, Naruto I already told you that."

"Aw well I guess Sai has to find out you like him." Naruto started to walk away with his hands behind his head.

Sakura ran up to him, covering his mouth and pulled him into the forest.

"Tell me what you know!" Sakura demanded.

"Well I know very well that you have a HUGE crush on Sai and I'm going to tell him." Naruto stated.

"What do I have to do to keep you quiet? Anything! Ramen, a kiss… WHAT?!?!?"

"A date or two!"

"WHAT?!?!"

"You heard me. I want a date or two!!!"

"Hell NO!!!"

"Ok then, SAI!!!" Sakura covered his mouth.

"Fine, just keep quiet. I don't want him to know."

"Alright Sakura-chan. See you later." Naruto said.

He gave her the flowers and gave her a big hug and pecked her on the lips. He ran off jumping and cheering. He left Sakura there mouth open blushing. She slowly walked home still mouth open.


The next night was Konoha festival. Everyone was celebrating the founding of Konoha. Everything was free and no one was on a mission or on duty. Everyone was just celebrating.

"So Tsu-chan! Are you ready?" Jiraiya asked.

"Yeah, I'm ready!" Tsunade said coming out of her room.

She looked totally miserable. She was frowning; she looked pretty pissed and stared daggers at Jiraiya.

"Come on Tsunade, look happy! It's nothing! I won't do anything to you. We have a double date with Naruto and Sakura anyway!" Jiraiya said.

"Thank God, Sakura is going to be there. Someone smarter than a monkey to talk to!" Tsunade said.

"Don't be so mean, Tsu-chan!"

"Shut up."

They walked into town where Naruto and Sakura were waiting for them at Ichiraku's. Naruto was having free ramen while Sakura sat miserably waiting for her Shishou to arrive and help her get through the night.

Jiraiya and Tsunade walk in and sit by them. Jiraiya sits by Naruto while Tsunade sits next to Sakura.

"So how are you holding in?" Tsunade asked.

"Shishou, arigato! I was going to go crazy!!! I mean Naruto blackmailed me into dating him. He threatened to tell Sai I like him." Sakura explained.

"Well Jiraiya bribed me into dating him. My debt to him from our last poker game will be even if I go on a date with him."

"Why do we have to be the ones who have such bad luck?"

"Well at least it's only one night." Tsunade said trying to make Sakura and herself feel better. But it didn't work.

"Alright ladies. Let's go." Jiraiya said.

They went to get dinner at the nice restaurant where Tsunade mostly drank Sake along with Sakura, who even though she was under age got permission from the Hokage.

Sakura drank up to 10 bottles and got a headache. Tsunade drank 12 and still feels fine. They were about to go on a moon light walk when Jiraiya bumps into an old friend.

"Hey Jiraiya, is that you?" Said a man.

"Tayato? Is that you?" Jiraiya asked.

Naruto and Jiraiya went over to talk to him while Tsunade and Sakura just sat down cursing their dumb luck. After a good long 20 minute conversation Jiraiya and Naruto went back to their dates.

"Let's go on a moonlit walk." Jiraiya said.

The girls went and actually saw the romantic side of Naruto and Jiraiya.

Jiraiya gave Tsunade as many roses as possible and gave her his jacket when she got cold, even though all he had under was a mesh shirt. He held Tsunade's hand and told her he thought she was beautiful.

Naruto kept his arm around Sakura and gave her his jacket as well to keep her warm. He kept complementing her over and over and said she was as beautiful as a spring cherry blossom that just bloomed.

When the night was over the four split up and the guys took the girls home.

"Well good night Sakura-chan." Naruto said.

"Night Naruto." Sakura said giving Naruto his jacket back and blushing.

"Sakura, can I ask you something?"

"What is it?"

"Will you go to this ball with me?"

"What, why should I? I mean you blackmailed me on this first date."

"Well I did say a date or TWO!!!"

"T-two!!! NARUTO YOU NO GOOD LITTLE BAKA!"

"That was the deal. Well see you tomorrow night Sakura-chan and make sure to look beautiful!" Naruto ran off before Sakura could kill him.


"So Tsunade remember our deal?" Jiraiya asked.

"Of course I do. One date and my debt is paid off." Tsunade stated.

"Well actually I said two dates. A date or two and I chose two."

"What? No you didn't!!!"

"Well yes I did. Ask Shizune and anyway theirs a ball tomorrow. You know it's Tayato's."

"WHY SHOULD I GO!?!"

"Well if you'd rather pay in money…"

"Fine you no good bastard."

"Good, see you tomorrow. 7 sharp. Stay beautiful." And he ran off before she could hit him.


Well I hope you like it!!! I know it's not good. Well R&R and tell me what I should improve! I know I'm not that good at writing but I hope you like this chapter!

Preview: Jiraiya and Naruto feel very guilty and get something for the girls to make up for what they did. They go to the ball and have a great time and fireworks fly. But how can the guys hold on to the girls' heart. Find out in chapter 4: Winning Hearts and Losing Hearts!