(Y/N) wakes up to the sound of his alarm clock as he slowly and groggily sits up in his bed and stretches his body. He looks to his window and takes in the magnificent morning view he has before standing up and heading to restroom to get ready for the day. And as he was brushing his teeth, he hears his scroll vibrating and sees that it is Professor Ozpin.
(Y/N): *SIGH* (Muffled from brushing) What now?
He picks up his scroll and answers it and displays the hologram.
Ozpin: Good morning (Y/N).
(Y/N): Morning sir. How can I help you?
Ozpin: Oh it's nothing important really. I am just calling every staff member, to let them know, that classes and shifts will be cancelled today.
(Y/N): Huh? Why is that?
Ozpin: I just figured that I allow the staff and students to enjoy the festivities and relax. We may be at a war with Salem and her Grimm, but I feel as though the children should still be children. Especially you and your sisters.
(Y/N): Hmm? Alright I get ya. I'll call my sisters and let them know. Thank you for the day off sir.
Ozpin: You are most welcome (Y/N). Oh, and one thing before I hang up.
(Y/N): (Grabs mouth wash) What's that? (Proceeds to gargle and swish mouth wash in mouth)
Ozpin: When are you going to ask Ms.Tsuyuri out on a date?
(Y/N) goes wide eyed and spits the mouth wash out of his mouth onto the mirror. He starts coughing and looks at Ozpin with a bright blush on his face.
(Y/N): W-WHAT?!
Ozpin: Well you see, me and some of the staff are-
Before he could finish his sentence, Glynda came over and cut the connection by ending the call. Probably to hide whatever mischievous plan Ozpin was about to reveal. (Y/N) rubs his temples as he tries to forget the embarrassment.
(Y/N): *SIGH* Stupid old man. I swear to Oum, I will shove that coffee mug down his-
*KNOCK!* *KNOCK!*
Kanao: (Y/N)?
Before he could finish that sentence, Kanao knocked on his door. He puts on a shirt and shorts and walks over to open his door so they could talk.
(Y/N): Yeah?
Kanao: Did you get a call from Ozpin?
(Y/N): Yeah. Why you ask?
Kanao: Cause I got a call from Glynda telling me that classes are cancelled for the day. So I was wondering if you got a similar call from Ozpin?
(Y/N): I did. He told me the same thing. Amongst additional topics.
Kanao: Hm?
(Y/N): N-Nothing!
Kanao: Okay? Well I was wondering if you wanted to spend the day with me, if that's alright?
(Y/N): Well actually I was...
Then that's when the memory of Ozpin asking when he's going to ask her out, came rushing back to him. And so, he made up his mind to do just that.
(Y/N): 'Damn you Ozpin.' You know what? Sure, why not. I got nothing better to do.
Kanao: Wonderful. Should we invite the girls?
(Y/N): Uh no, I thought it could just be us.
Kanao freezes in place as she tries to take in the words that came out of (Y/N)'s mouth.
Kanao: Just us?
(Y/N): Yep.
Kanao: The two of us?
(Y/N): Uh huh.
Kanao: Alone? Together?
(Y/N): Uh... pretty much.
Kanao: ....................................
(Y/N) waves his hand in front of her face to try and break her out of her trance.
(Y/N): Kanao?
Kanao: .......... Sure.
(Y/N): Huh?
Kanao: Sounds like fun. I'll go get ready.
She then walks off to her room, enters her room and closes it. She then walks over to her bed, flops down and buries her face into her pillow and kicks her legs up and down and squeals happily.
Kanao: 'Oh Oum it's finally happening! I need a shower, I need to brush my teeth and my hair and I need to pick a cute outfit! But what do I wear?' I need to call Lana, she's the only one who can help!
Back in (Y/N)'s room, he was his own mental crisis.
(Y/N): 'Oh my Oum. What am I doing?! This is the most stressful thing I've ever done!' Ugh! I need to call Sam to help me out!
*Time-skip*
(Y/N) and Kanao were now out on the town, walking the streets and exploring the festivities. And boy were they embarrassed. Their faces were bright red and they both looked extremely nervous to be near each other.
(Y/N): 'Oum damnit! Sam you better be right about this!' So uh... where do you wanna go first?
Kanao: Well... um... how about-
(Y/N): Kanao?
Kanao: *SNIFF* *SNIFF* ......... Mochi.
(Y/N): Wait wha-
Before he could even ask his question, Kanao was already across the street and looking through a glass window of a mochi shop.
(Y/N): Oh. Mochi's a great start I guess.
He makes his way over to Kanao, notices her staring at all of the cutely decorated sweets.
Kanao: So cute. So delicious.
(Y/N): You and your sweet tooth I swear. Your almost as bad as Ruby. But just as cute.
Kanao: W-w-what?
(Y/N): Uh n-nothing! (Walks up the vendor) Can I get two please?
Vendor: What flavors sir?
(Y/N): Uh one strawberry for my friend and one (F/F) for me, please.
( (F/F) means favorite flavor in case you didn't know. )
Vendor: Coming right up.
The vendor walked away for a moment and came back with the two flavored mochi's and handed them to (Y/N). (Y/N) pays for the sweets, thanks the vendor, and hands Kanao her flavor. They then continue walking down the street as they enjoyed their sweets.
Kanao: Mmm~! So good!
(Y/N): You act like Ruby when she eats her cookies. And it's adorable.
Kanao: Hm? What did you say?
(Y/N): Uh n-n-nothing! Soooooo what do you wanna do next?
Kanao: No idea. But I say we keep walking and enjoy the sights.
(Y/N): If you say so.
As the two of them kept on walking, they did not realize (Y/N)'s sisters were stalking them along with Sam in the background.
Sam: Oh for the love of Oum. Just tell her you idiot!
Ruby: Uncle Sam?
Sam: Yes Rubes?
Ruby: Why are we doing this?
Sam: Just think Ruby, wouldn't you wanna see your brother finally date the love of his life? Don't you wanna be there for when he proposes? Or when their first child comes? Or-
Yang: This is about the bet isn't it?
Sam: ..................
Sam grabs the girls into a huddle and converses with them.
Sam: How did you girls know?
Blake: You staff don't know when to keep things secretive. Especially around us.
Sam: Okay you got me. But that is half the reason. I really want him to stop acting like a pansy and just ask her out already.
Weiss: And as Ruby said, why are we stalking them?
Sam: So that we can make sure that this goes off without a hitch. No disturbances, no distractions, no nothing. Got it?
RWBY: Roger.
Sam: Good. Now show me what you girls learned in stealth class. Especially you Yang.
RWB_: Understood!
Yang: Hey!
And with that, Ruby, Blake and Sam take to the roofs while Weiss and Yang took to the streets. As the stalkers... stalk the love birds, they made sure that nothing came to interrupt them. Their was the occasional street trash that wanted to try and woo over Kanao or the female... "workers" that would try and steal (Y/N) attention. But that was all taken care of by the security team. It was now late at night and the love birds were at the park that was mysteriously empty. Thanks to a few individuals. Not just the stalkers but also a few others that were in on the bet.
Kanao: You know, today has been a fun day.
(Y/N): Yeah. Been awhile since we could just have fun and not worry about real world. I do wish that Michael was here. He would've taken all of us around town. Wasting our money and time to do just about everything.
Kanao: .... You really do miss him. Don't you?
(Y/N): ........... Why wouldn't I? He wasn't just my partner. He was my brother.
They stop walking and look up into the night sky and the shattered moon.
Kanao: You know... I think Michael would be proud of you.
(Y/N): How so?
Kanao: Well for one, he always wanted to teach the new generation of huntsman and huntresses. And your doing a fine job at that as a combat instructor. And two, it was to help others that can't help themselves. And you becoming a legendary huntsman has certainly done that.
(Y/N): I just wish he was here with us. We could all be achieving our dreams together.
Kanao: 'Okay you can do this Kanao.' Well my dream hasn't been achieved yet.
(Y/N): And what's your dream exactly?
Kanao: .... You.
And with that said, (Y/N) goes wide eyed and turns to face her as she does that same.
(Y/N): W-what?
Kanao: You. You're one of my dreams. To fall in love with a man that's always strong and dependable. A loving and caring individual who sees the best in everyone. And someone who has the biggest and kindest heart. That's the kind of man who I want to love for the rest of my life.
(Y/N): ........ Well I uh... I don't know what to say.
Kanao: Well you can answer me this one question?
(Y/N): And that is what?
Kanao: Will you be my... boyfriend?
(Y/N) smiles warmly as he places his lips against her own which caught her off guard for a second before she returned the kiss back with the same romantic passion. Elsewhere, behind a couple of trees, team RWBY and Sam were cheering silently while Sam was recording the whole thing on his scroll. (Y/N) and Kanao break apart from their kiss as they hold each other close as they look up at the moon lit sky.
(Y/N): Was your dream achieved?
Kanao: Yes. Yes it was.
And done. Sorry for making this a shorter chapter. I wanted to make the main story and little side stories separate from each other because I have some plans for little side chapters in the near future. Also I wanna continue some of my other stories like my Erma fanfic that a lot of you guys seem to like. Anyways, stay rockin' rockstars!