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Description
(A/n: If you're wondering, this is non-canonical to my ongoing Ruby x Male Reader series, however, it still takes place in that universe, (basically, just think of it as a side story that happened between episodes)

Lily stands in front of a seated (Y/n), pointing to numerous things on a whiteboard behind her.

(Y/n): I still don't get it.

Lily: What is there not to get? (sighing) Valentine's day is tomorrow, which means you have to do something romantic with Ruby!

(Y/n): R-right, but why does something special have to happen on Valentine's day? Can't I just go out with her normally?

Lily: Of course you can't!

(Y/n): Eh?! Why not?

Lily: Because that's not what Valentine's Day is all about. It's where you are together with the one you cherish, eating at an expensive restaurant, whilst a violin plays in the background and you look each other deep in the eyes as-

(Y/n): That's not really my style though...

Lily: Shut up! I wasn't finished!

Evan: (walking into the room) We really need to find you someone otherwise you'll continue to influence Cap's and Ruby's relationship.

Lily: I do not influence their relationship in any way whatsoever!

Evan: You are literally dismissing what (Y/n) is saying in favour of your own idea.

Lily: Well...

Evan: And just the other day you tried to convince Ruby that dressing more risque would attract (Y/n)'s attention more.

Lily: It worked didn't it?

Evan: Yeah, to the point that (Y/n) instantly got a nosebleed and passed out, and Ruby was embarrassed into a state of shock.

Lily: Fine! What do you propose, oh mister love-guru?

Evan: Calm yourself, I was just suggesting that maybe you were enforcing your thought of a 'perfect date' onto (Y/n) too much. Though if you are asking me... how about (Y/n) makes some chocolate to give to her? (to (Y/n) I could show you how to make some.

(Y/n): That's a good idea actually, though instead of chocolate, how about we make some cookies? They are her favourite after all.

Evan: Sure. Now that that is sorted, we have another dilemma.

(Y/n): What is it?

Evan: I can't find Barry anywhere.

Barry: (bursting through the door, violin in hand) I believe someone called for a violinist?

(Y/n): Sorry bro, we're not doing that anymore.

Barry: Wait, we're not? Oh man... Do you know how hard it is to smoothly work your way into a position to show off your violin skills? Really hard. (sighing) Whatever...

(Y/n): Hey, wait, maybe not all is lost.

Barry: What do you mean?

(Y/n): Lily wants a romantic dinner with a violinist playing for her correct? Well, why can't you be both?

Lily: WHAT?! There is no way in hell that I'm going on a date with (pointing at Barry) that!

Barry: Hey! What's that supposed to mean? And why are you so against the idea of going on a date with me?

Lily: (flustered) W-well, it's b-because...

Barry: Wait a second! Don't tell me that the infamous Lilac Lover, known for toying with the emotions of men and stabbing them in the back, has fallen for the most handsome member of Team REBL?

Lily: It's not that at all! I don't have a crush on (Y/n)!

Barry: That's not who I meant when I said most handsome in the team!

(Y/n): (as the two continue to bicker) Evan, can you do something?

Evan: (quietly) Always the peace-maker... (regaining composure) What's that Barry?

Barry: (confused) What's what?

Evan: That, between our beds. (walks over to it and picks it up) A bouquet of flowers? Addressed to Lily no less! I guess he really does care for you! And it also appears that there is a reservation for you two tomorrow at the most expensive restaurant in town!

Lily: (surprised) R-Really?

Evan: (shoving the flowers into Barry's chest) Go on then. I know you've wanted to do this for a while.

Barry: (nodding at Evan) So... (presenting the flowers to Lily) are you in?

Lily: (questioning) That's the best you could come up with? (shrugging it off and smiling) Of course, ya stupid idiot!

Barry: Great!

Evan: (whispering into Barry's ear) You don't actually have a reservation to the most expensive restaurant in Vale. I suggest you do something about that...

Lily: (oblivious to their whispering) Oh this is going to be the best day ever! Finally, I'll be able to truly go on an actual date which doesn't involve me killing the person I'm going out with!

Evan: Unless you want to meet the same fate as the others.

Barry: (panicking) W-well, I'd love to stay and chat, b-but I've got to go somewhere! (running out) Catch you guys later!

Evan: Good, that's sorted. (to (Y/n) We gonna make some cookies or what?

(Y/n): Oh you bet your ass we are!

Time Skip
---------
Yang: He hasn't said anything to you at all?!

Ruby: Well, no... But he's still new to all of these holidays and stuff! I mean, he just had his first Christmas a couple months ago, he might just not know what Valentine's Day is yet.

Weiss: Still, you guys haven't been out together for a while now...

Yang: Well, maybe he was just thinking of something really big to surprise you with! Isn't that right Blake?

The cat Faunus looks up from the book she's reading and shrugs.

Yang: See? Blake thinks so too! (hearing a knock on the door) That's probably him now.

(Y/n): (outside Team RWBY's dorm room and hearing their conversation) Umm, yeah (looking at his box of cookies) big surprise...

Yang: (opening the door and seeing (Y/n) Hey (Y/n)! Need me to get Ruby for ya?

(Y/n): Yeah, thanks, Yang.

The yellow-haired woman nods and then a few moments later a certain scythe-wielding huntress appears, slightly blushing.

Ruby: H-hey, Wolfie. What's up?

(Y/n): Well, I uh, wanted to give you these. (hands the box over to her)

Ruby's eyes sparkle and she practically snatches the box out of the wolf Faunus' hands. However before she opens the lid, she looks over to (Y/n) to see if she has permission to eat some now, to which the (H/c) haired male laughs slightly and nods his head. Ruby tears off the lid and starts shovelling cookies into her mouth.

Ruby: (speaking with her mouth full) Thewse are wellry goosch!

(Y/n): (shaking his head but smiling) We've talked about this. Chew first, then talk.

Ruby nods her head before swallowing the cookies in her mouth and addressing her boyfriend again.

Ruby: They were really good! Thanks (Y/n)!

(Y/n): I'm glad you liked them, I made them myself.

Ruby: (amazed) Really?!

(Y/n): Well, with some help from Evan, but yeah, it was mostly me.

Ruby: That's super cool! You have to make me some more some time!

(Y/n): Just say so and I'll whip up a batch as quickly as I can. But uh (getting flustered) th-that's not what I came here to do.

Ruby: (curious) Then, what was it?

(Y/n): Um, as you may know, Valentine's Day is tomorrow, and I was wondering, if you uh, wanted to have a picnic? I uh, know it's not that extravagant, you probably wanted a candlelit dinner like Lily suggested but I just thought that maybe-

Ruby: (cutting him off) You talk too much sometimes, you know? I don't care what we're doing, so long as I get to do it with you. (kissing him on the cheek) And a formal dinner isn't really my style either, I'd much prefer a picnic.

(Y/n): Well, uh, great! I'll pick you up at around 7, does that sound good to you?

Ruby: Amazing.

(Y/n): Good, I'll see you then, then?

Ruby: (smiling) Yes you will Wolfie, see you tomorrow.

Time Skip
---------
Barry: (as (Y/n) fixes the tie on his suit) I'm nervous, man, how are you not nervous for your date?

(Y/n): Because I know that no matter what happens, I'll have a great time. You need to think like that too.

Barry: You're right. Though what if I mess up? She's really aggressive you know.

Lily: She's also still in the room. (sighing but then smiling sweetly at him) You'll do fine, I know you will. So get off your ass and grab my hand, will you?

Barry: (grabbing her hand) R-right. We'll see you guys later.

Evan: Have a good time.

Barry and Lily wave me and Evan and then head off into the streets of Vale.

Evan: (to (Y/n) You ready for your date?

(Y/n): (motioning to the basket placed on the side) As ready as I'll ever be. Are you gonna be alright big guy? I don't really want to leave you on your own.

Evan: (amused) Who said I was gonna be alone?

(Y/n): What? I thought you-

Evan: You thought, you didn't know. I'll have you know I have a lady of my own to be out and about with.

(Y/n): Who would that be?

Evan: For me to know and you to not find out my friend. Right, I best be off, you should too, don't want to keep her waiting, do ya?

(Y/n): Of course I don't, see ya later dude.

We head our separate ways as I make my way over to Team RWBY's dorm room. The love of my life opens the door and smiles.

Ruby: I hope you don't mind I wear my usual gear.

(Y/n): I wouldn't have it any other way.

Time Skip
---------
As the night draws to a close, you smile at the now sleeping Ruby on your shoulder. You pick her up bridal style and head back over to her dorm. Gently placing her back into her bed, you kiss her forehead and then go to leave, that is until a hand tugs at your arm.

Ruby: Stay...

(Y/n): And here I thought, we weren't doing the cliche Valentine's Day stuff.

Nonetheless, you comply with your girlfriends wish and get into bed with her.

Ruby: (whilst snuggling into you) You really are special, you know that?

(Y/n): Special in a good way or...?

Ruby: (giggling) Special to me! You've helped me since our first day at Beacon, I don't know what I would've done without you.

(Y/n): I could say the same to you. You discarded what anyone had said about me, what I did in the past, and you saw me as a good person no matter what I did. I can't thank you enough for that.

Ruby: The only reason I said you're a good person is because you are, at least to me. I love you (Y/n).

(Y/n): I love you too Ruby.

Description
(A/n: If you're wondering, this is non-canonical to my ongoing Ruby x Male Reader series, however, it still takes place in that universe, (basically, just think of it as a side story that happened between episodes)

Lily stands in front of a seated (Y/n), pointing to numerous things on a whiteboard behind her.

(Y/n): I still don't get it.

Lily: What is there not to get? (sighing) Valentine's day is tomorrow, which means you have to do something romantic with Ruby!

(Y/n): R-right, but why does something special have to happen on Valentine's day? Can't I just go out with her normally?

Lily: Of course you can't!

(Y/n): Eh?! Why not?

Lily: Because that's not what Valentine's Day is all about. It's where you are together with the one you cherish, eating at an expensive restaurant, whilst a violin plays in the background and you look each other deep in the eyes as-

(Y/n): That's not really my style though...

Lily: Shut up! I wasn't finished!

Evan: (walking into the room) We really need to find you someone otherwise you'll continue to influence Cap's and Ruby's relationship.

Lily: I do not influence their relationship in any way whatsoever!

Evan: You are literally dismissing what (Y/n) is saying in favour of your own idea.

Lily: Well...

Evan: And just the other day you tried to convince Ruby that dressing more risque would attract (Y/n)'s attention more.

Lily: It worked didn't it?

Evan: Yeah, to the point that (Y/n) instantly got a nosebleed and passed out, and Ruby was embarrassed into a state of shock.

Lily: Fine! What do you propose, oh mister love-guru?

Evan: Calm yourself, I was just suggesting that maybe you were enforcing your thought of a 'perfect date' onto (Y/n) too much. Though if you are asking me... how about (Y/n) makes some chocolate to give to her? (to (Y/n) I could show you how to make some.

(Y/n): That's a good idea actually, though instead of chocolate, how about we make some cookies? They are her favourite after all.

Evan: Sure. Now that that is sorted, we have another dilemma.

(Y/n): What is it?

Evan: I can't find Barry anywhere.

Barry: (bursting through the door, violin in hand) I believe someone called for a violinist?

(Y/n): Sorry bro, we're not doing that anymore.

Barry: Wait, we're not? Oh man... Do you know how hard it is to smoothly work your way into a position to show off your violin skills? Really hard. (sighing) Whatever...

(Y/n): Hey, wait, maybe not all is lost.

Barry: What do you mean?

(Y/n): Lily wants a romantic dinner with a violinist playing for her correct? Well, why can't you be both?

Lily: WHAT?! There is no way in hell that I'm going on a date with (pointing at Barry) that!

Barry: Hey! What's that supposed to mean? And why are you so against the idea of going on a date with me?

Lily: (flustered) W-well, it's b-because...

Barry: Wait a second! Don't tell me that the infamous Lilac Lover, known for toying with the emotions of men and stabbing them in the back, has fallen for the most handsome member of Team REBL?

Lily: It's not that at all! I don't have a crush on (Y/n)!

Barry: That's not who I meant when I said most handsome in the team!

(Y/n): (as the two continue to bicker) Evan, can you do something?

Evan: (quietly) Always the peace-maker... (regaining composure) What's that Barry?

Barry: (confused) What's what?

Evan: That, between our beds. (walks over to it and picks it up) A bouquet of flowers? Addressed to Lily no less! I guess he really does care for you! And it also appears that there is a reservation for you two tomorrow at the most expensive restaurant in town!

Lily: (surprised) R-Really?

Evan: (shoving the flowers into Barry's chest) Go on then. I know you've wanted to do this for a while.

Barry: (nodding at Evan) So... (presenting the flowers to Lily) are you in?

Lily: (questioning) That's the best you could come up with? (shrugging it off and smiling) Of course, ya stupid idiot!

Barry: Great!

Evan: (whispering into Barry's ear) You don't actually have a reservation to the most expensive restaurant in Vale. I suggest you do something about that...

Lily: (oblivious to their whispering) Oh this is going to be the best day ever! Finally, I'll be able to truly go on an actual date which doesn't involve me killing the person I'm going out with!

Evan: Unless you want to meet the same fate as the others.

Barry: (panicking) W-well, I'd love to stay and chat, b-but I've got to go somewhere! (running out) Catch you guys later!

Evan: Good, that's sorted. (to (Y/n) We gonna make some cookies or what?

(Y/n): Oh you bet your ass we are!

Time Skip
---------
Yang: He hasn't said anything to you at all?!

Ruby: Well, no... But he's still new to all of these holidays and stuff! I mean, he just had his first Christmas a couple months ago, he might just not know what Valentine's Day is yet.

Weiss: Still, you guys haven't been out together for a while now...

Yang: Well, maybe he was just thinking of something really big to surprise you with! Isn't that right Blake?

The cat Faunus looks up from the book she's reading and shrugs.

Yang: See? Blake thinks so too! (hearing a knock on the door) That's probably him now.

(Y/n): (outside Team RWBY's dorm room and hearing their conversation) Umm, yeah (looking at his box of cookies) big surprise...

Yang: (opening the door and seeing (Y/n) Hey (Y/n)! Need me to get Ruby for ya?

(Y/n): Yeah, thanks, Yang.

The yellow-haired woman nods and then a few moments later a certain scythe-wielding huntress appears, slightly blushing.

Ruby: H-hey, Wolfie. What's up?

(Y/n): Well, I uh, wanted to give you these. (hands the box over to her)

Ruby's eyes sparkle and she practically snatches the box out of the wolf Faunus' hands. However before she opens the lid, she looks over to (Y/n) to see if she has permission to eat some now, to which the (H/c) haired male laughs slightly and nods his head. Ruby tears off the lid and starts shovelling cookies into her mouth.

Ruby: (speaking with her mouth full) Thewse are wellry goosch!

(Y/n): (shaking his head but smiling) We've talked about this. Chew first, then talk.

Ruby nods her head before swallowing the cookies in her mouth and addressing her boyfriend again.

Ruby: They were really good! Thanks (Y/n)!

(Y/n): I'm glad you liked them, I made them myself.

Ruby: (amazed) Really?!

(Y/n): Well, with some help from Evan, but yeah, it was mostly me.

Ruby: That's super cool! You have to make me some more some time!

(Y/n): Just say so and I'll whip up a batch as quickly as I can. But uh (getting flustered) th-that's not what I came here to do.

Ruby: (curious) Then, what was it?

(Y/n): Um, as you may know, Valentine's Day is tomorrow, and I was wondering, if you uh, wanted to have a picnic? I uh, know it's not that extravagant, you probably wanted a candlelit dinner like Lily suggested but I just thought that maybe-

Ruby: (cutting him off) You talk too much sometimes, you know? I don't care what we're doing, so long as I get to do it with you. (kissing him on the cheek) And a formal dinner isn't really my style either, I'd much prefer a picnic.

(Y/n): Well, uh, great! I'll pick you up at around 7, does that sound good to you?

Ruby: Amazing.

(Y/n): Good, I'll see you then, then?

Ruby: (smiling) Yes you will Wolfie, see you tomorrow.

Time Skip
---------
Barry: (as (Y/n) fixes the tie on his suit) I'm nervous, man, how are you not nervous for your date?

(Y/n): Because I know that no matter what happens, I'll have a great time. You need to think like that too.

Barry: You're right. Though what if I mess up? She's really aggressive you know.

Lily: She's also still in the room. (sighing but then smiling sweetly at him) You'll do fine, I know you will. So get off your ass and grab my hand, will you?

Barry: (grabbing her hand) R-right. We'll see you guys later.

Evan: Have a good time.

Barry and Lily wave me and Evan and then head off into the streets of Vale.

Evan: (to (Y/n) You ready for your date?

(Y/n): (motioning to the basket placed on the side) As ready as I'll ever be. Are you gonna be alright big guy? I don't really want to leave you on your own.

Evan: (amused) Who said I was gonna be alone?

(Y/n): What? I thought you-

Evan: You thought, you didn't know. I'll have you know I have a lady of my own to be out and about with.

(Y/n): Who would that be?

Evan: For me to know and you to not find out my friend. Right, I best be off, you should too, don't want to keep her waiting, do ya?

(Y/n): Of course I don't, see ya later dude.

We head our separate ways as I make my way over to Team RWBY's dorm room. The love of my life opens the door and smiles.

Ruby: I hope you don't mind I wear my usual gear.

(Y/n): I wouldn't have it any other way.

Time Skip
---------
As the night draws to a close, you smile at the now sleeping Ruby on your shoulder. You pick her up bridal style and head back over to her dorm. Gently placing her back into her bed, you kiss her forehead and then go to leave, that is until a hand tugs at your arm.

Ruby: Stay...

(Y/n): And here I thought, we weren't doing the cliche Valentine's Day stuff.

Nonetheless, you comply with your girlfriends wish and get into bed with her.

Ruby: (whilst snuggling into you) You really are special, you know that?

(Y/n): Special in a good way or...?

Ruby: (giggling) Special to me! You've helped me since our first day at Beacon, I don't know what I would've done without you.

(Y/n): I could say the same to you. You discarded what anyone had said about me, what I did in the past, and you saw me as a good person no matter what I did. I can't thank you enough for that.

Ruby: The only reason I said you're a good person is because you are, at least to me. I love you (Y/n).

(Y/n): I love you too Ruby.