'There he goes, out of the cave entrance with Kakazu and Hidan. Most likely going to accompany them on another bounty hunt. We are not exactly low on supplies and in dire need of resources. I think it is out of sheer boredom that they were even going. Although, it's easy to understand why the other two were going. Kakazu was a money grubber and Hidan loved to kill things, so those two were perfect for the job description. But it was a bit odd that Tobi was tagging along.' (Y/n) sat there with her chin rested on her palms as she thought about the odd situation. He never usually hung out with the infamous KakaHida, but she wasn't too worried about it. All she could focused on right now was watching him walk out of that cave and catch her last glimpse of him to lock away in her mind for the time he'd be away. Their bounty hunts usually took a few days and she wanted his image burned into her brain. As she was lost in her thoughts, she heard a loud voice calling out her name. As she was snapped back into reality, she saw that Tobi was calling out to her waving his hand frantically. (Y/n) jolted and looked at him like a stunned deer. "(Y/n)-Chan! I'll see you when I get back!" 'Phew, thank Kami he didn't notice me staring'. "Um... yeah! I will see you soon Tobi-kun." she replied with a light blush. But of course, Tobi didn't notice it. Before she could ask when they would be back, they were already out of sight.
(Y/n) sighed and closed her eyes going back to that mental snapshot she had taken. Wow, he was so cute. I mean sure he wore a mask and had that huge red clouded overcoat on his shoulders, but she still melted whenever he was in the room. There had been a few times she was blessed to have seen him without his Akatsuki jacket on and have a good glimpse at his body build, even if it was through tight fitted clothing. 'Sweet Kami, he was built.' His toned arms made her weak at the knees. His washboard stomach made her breath heavy. Probably the most torturous thing of all was the fact he didn't even know how attractive he was. Well, attractive to (y/n) anyways. That was another thing she loved about Tobi, his naïve, silly personality. Sure, it got on the other's nerves when he would spaz out from a sugar rush, but that was just part of the Tobi package she had invested into and she loved it all the same.
It was a bit amusing at times, seeing how irritated Deidara would get over his artwork being insulted so casually and Hidan getting constant hugs in the morning. The very thought of it made (y/n) giggle. "You're not thinking about Tobi again, are you?" (Y/n) gasped. She looked up to see who was accusing her only to find none other than Itachi Uchiha. "Shhhhhh, keep it down! You don't want the whole base to hear now, do you!?" The right corner of Itachi's lips lifted into an amused smirk as he watched the frantic (y/n) search left and right for any ears droppers. "Relax, there is no need to be so agitated. Tobi is long gone by now and there is no one around to hear us." (Y/n) loosened her tense muscles as she was reassured that her secret remained a secret, with the exception of Itachi of course.
Itachi had been a confidant of hers since the first day she was initiated into the Akatsuki. He was always very quiet and mostly kept to himself. Although over the first couple of weeks, he had warmed up to (y/n) and eventually became very good friends with her. Whenever (y/n) had a problem with something or needed to vent out her frustrations, Itachi was always there to hear her out. He wasn't a big talker himself, but he would always offer her an ear to chew off while she rambled on about her troubles. That, and he would always give her his opinion which seemed to answer her question or relieve her stress. Sure, half of the stuff she raved on about was a bit repetitive and meaningless, but it reminded him of what it was like to have a younger sibling. To coach them and always look out for them. It warmed his heart and gave him an almost nostalgic feeling. The most recent thing (y/n) had been talking about was Tobi. How funny Tobi was, how cute Tobi was and how special Tobi was. It was funny to see how much she would rave on about the orange masked man but as soon as he was in the same room, she would melt like butter. She needed some coaching in this department for sure.
Itachi was about to start his 'coaching' when he heard Deidara and Sasori coming into the living room. They were most likely going to watch a show like Pimp My Ride or LA Ink, something to do with art. Seeing that their privacy had been disrupted, the Uchiha ushered (y/n) to follow him down the hallway which lead to his room. Normally, he would allow no one to enter his room, but (y/n) was an exception. After entering the dim and tidy room, Itachi closed the door softly as (y/n) sat on his bed. She patted the space in front of her guiding him to side down in front of her. "So, what did you want to talk about Itachi-kun?" Itachi took a breath before he started his discussion. "You need help"
(Y/n) leaned her head back and gave Itachi an 'are you serious' look. "Well I know I'm not as calm and collected as you are, but I wouldn't say I need help... Oh great and mighty Senpai" (y/n) replied emphasising on the sarcasm in the phrase 'oh great and mighty Senpai'. Itachi sunk his head slightly with closed eyes, ever so slightly smiling at how quick she was to jump the gun. "I didn't mean to imply you were mentally unstable, (y/n). What I mean to say is you need help in regards to your courtship with Tobi." As soon as the name 'Tobi' was mentioned, (y/n)'s cheeks tinted with a bright pink hue. "What m-makes you think I want to go out with T-Tobi?" This time it was Itachi's turn to give her an 'are you serious' look. "Maybe it's the fact you turn as bright as a tomato every time he is near you?" (Y/n) scowled and turned her head in the opposite direction knowing full well that everything Itachi had said was spot on. She did like Tobi and she knew she wanted to go out with him. Her only problem was that she was so damn shy and knowing the childish persona Tobi had, it would be very unlikely he would initiate anything. Therefore, it was up to her to make a pass at him. This is where Itachi came into the picture. He; being her courting coach, would give her tips and show her how to crack onto Tobi.
(Y/n) gave up and turned to Itachi with a defeated look. "Well, how do you plan on helping me with Tobi?" (Y/n) finally asked Itachi who had not since budged from his previous position. "Normally I would suggest the first thing we would do is find out if he likes you. But knowing Tobi, you won't get a solid answer out of him. So our best plan of attack is to make the first move." Making the first move is a big ask. Considering she feels like jelly every time he is in the same room. If she can get that worked up over him being near her, how the hell was she supposed to crack onto him!? Would he notice, or would he just play it off as a friendly gesture? What if he did catch on and he rejected her. Hard-core rejected her. No, that couldn't happen to her, she would never be able to face a man again if Tobi of all people rejected her. Gosh, it was so confusing!
Almost as if sensing the civil war going on in her head, Itachi placed a comforting hand on her shoulder to almost figuratively wash away her doubts. "It will all be fine. I promise." Man, it was just like Itachi to say the simplest things to ease her mind. (Y/n) looked at him and smiled. "Thank you Itachi-kun. You always know exactly what to say to make things better." She leaned in and hugged him as a gesture of her gratitude.