It's not a quest. Seriously. Quests have, uh, dragons and stuff. Getting Weiss to go out with her doesn't count as a quest.
But it is so much fun to call it a quest, and Yang is much more likely to help her if she makes it sound cool.
Ruby corners her big sister when Weiss and Blake are both studying in the library, without their teammates (Weiss gave them a little disapproving look when she said that), and Yang is sprawled across her bed, tapping at her scroll.
"Hey, Yang. How's it going?" Ruby asks, giving her a friendly casual smile as she hops up so she can sort of see Yang.
"Ruby, what's wrong?" Yang puts her scroll down and grabs Ruby's face, pushing it back and forth to study it.
"What? Why would something be wrong?"
"You're trying to be casual about something," Yang says, and Ruby sighs. Is she that bad at being casual? "Did you break Ember Celica again?"
"No, no, it's nothing like that!" Ruby squeaks, writhing out of Yang's grip. "I just want advice!"
"Good," Yang says, eyes fading from red to purple. "What's going on? Do you need me to beat someone up for you?"
"I don't need you to protect me," Ruby insists, crossing her arms.
"Rubes, I'm just looking after you because I'm your sister and I care about you." Yang ruffles Ruby's hair. "Anyway, if you're looking for wise advice, you have – probably come to the wrong place, actually."
"Well, I figured you at least know more about love than I do," Ruby offers.
"Is it Weiss?"
Wow, that's a rude assumption to make. They're friends, and they're close, or Ruby is close and Weiss is sometimes okay with it. But not every friendship has some sort of simmering erotic tension beneath the surface. Sometimes friendship is just friendship.
Okay, it is Weiss, but is it really that obvious?
"How did you know?" Ruby asks.
Yang shrugs.
"Lucky guess. Need my help to woo the Ice Queen?"
"She's not an ice queen! She's very nice, deep down."
"I'm sure she is." Yang slides her Scroll into her pocket and drops to the floor. "What you need is a grand romantic gesture."
"But when Jaune –"
"Jaune doesn't understand the concept of 'cool' or 'romantic'," Yang interrupts. "I do. All you need to do is follow my advice, and my advice is a grand romantic gesture. If you just walk up to her and ask her out, she'll turn you down on instinct, but if you put effort into it, she'll be more inclined to say yes. It's very logical."
That makes a surprising amount of sense.
"Okay, what should I do?"
"Make a classic rom-com gesture. Stand outside her window with a boombox," Yang says, waving her hands vaguely in the air.
"It's our window, not just her window," Ruby points out.
"I'll get Blake out. That's not a problem."
And just like that Ruby has a plan. If this were combat, Weiss would tell Ruby it's a terrible plan, the same way she always does, but Weiss isn't here, so Ruby's never been more confident in her planning skills.
…
It's too early to be actually doing anything, but according to Yang this is a good time. Ruby can't see more than vague outlines of stuff.
Which might be a problem, since she can't actually remember which window is hers. The regulation curtains are tightly drawn across each two-stories-up pane.
Fortunately, Ruby is a smart person, so the solution presents itself immediately. All she has to do is go up to the hallway and see how many doors are between their room and the wall.
It's a brilliant plan until she forgets how many doors there were. It's six or seven, and she doesn't feel like running back up the stairs again to go check. Six, probably. Worst case scenario, she's wrong.
Ruby starts throwing rocks at the sixth window, but carefully, because breaking it would really not endear her to Weiss. After the third or fourth pebble, someone calls "hold on a minute!" It sounds like Weiss, or at least Weiss when she's still half-asleep.
Ruby turns on the music and holds the boombox over her head, wishing that Yang would have been willing to compromise and just use a Scroll for the music, because real speakers are heavy. The window creaks open with agonizing slowness, and Ruby hoists the boombox higher, offering a hopeful grin.
Weiss looks taller. And it might just be the orange light of the sunrise, but it seems like she changed her hair.
Oh.
Pyrrha, hair out of its usual ponytail and falling to her waist, still blinking away sleep, smiles gently.
"Ruby, while this is very sweet of you, I'm afraid I have to turn you down."
Ruby squeaks in horror and hastily turns off the boombox, which is now producing lyrics about eternal, everlasting love.
"No, no, it's okay, I mean, this wasn't for you –"
Pyrrha slowly retreats and closes the window, presumably to give Ruby time to cry and lick her wounds. Well, Ruby might be embarrassed, but she is determined. And, hey, now she knows which window it is.
Weiss sleeps like a log, or a rock, or something else heavy that doesn't move until it gets up at precisely six-thirty AM and is then perfect and precise and doesn't spend any time being sleepy, no matter how little sleep she got. That's not a problem. Ruby just needs to find bigger rocks.
In retrospect, it should have been very obvious what was going to happen next.
On the bright side, tossing a half-brick from the courtyard through the window of Team RWBY's dorm room does indeed wake Weiss up.
"What is going on?" Weiss demands, sticking her head out of the wreckage of the window. Ruby hastily picks up her boombox.
"Ruby, forgetting your dorm key yet again does not give you justification to break in like some kind of hooligan!"
"No, that's not what happened!"
"So you broke the window for no reason?"
"It was an accident, I swear!" Ruby calls up to the window.
"Why were you throwing rocks at the window?"
Weiss is clearly not in the mood for romance, so Ruby gives up and trudges back inside to help clean up the glass.
A/N: I don't make a habit of watching romcoms, so if you have ideas for more grand romantic gestures to go horribly wrong, suggest them in a review or PM.