AN: RWBY belongs to Monty Oum and Rooster Teeth Productions
Jaune Arc sat on a bench alone in the courtyard of Beacon Academy. As he watched the other students pass by and thought on his time here and how much more... eventful it had been than expected. I mean sure he had expected to fight grimm, that was the entire point after all! But he didn't expect to be wrapped up in that whole white fang conspiracy last year, nor did he expect to have dated a gorgeous pro-athlete huntress.
Although that last one led to his current problem, he had been dating Pyrrha, but now he wasn't. Now this itself was not the problem, it had been a mutual breakup due to lack of shared interests, other than sword combat in which one combatant had been the girl who had won the Mistral Regional tournament four years in a row and the other had been, well... Jaune.
However the reason this breakup had caused problems for Jaune was because once again the dance was coming up, and this time Pyrrha did have a date which meant that once again he would have to either embarrass himself in the pursuit of his own date or go alone. The answer was obvious of course, which led to the real reason for his observation of the courtyard, Pyrrha had once said that there were plenty of fish on the sea, so Jaune had decided to go fishing.
He stood up as he saw an attractive brown haired girl walk past and approached her,
"Hey sunshine, how would you feel about going to the dance with me, Jaune Arc, defeater of White Fang, Combaterof Criminal Conspiracies aaaannnd," he paused for dramatic effect, "natural blonde."
The girl stared at him for a few seconds before bursting into laughter, "You, Defeater of the White Fang?" she continued laughing," No thanks, I'll pass," she spoke before turning and walking away.
Jaune groaned, collapsing onto his bench, "It's no use, you can't go fishing if you don't have any bait."
"You're going fishing?" a voice spoke from behind him. Jaune turned to see Ruby Rose, head tilted and looking rather confused.
"No," Jaune replied, "It was a metaphor... thing, I dunno." He sighed
"Oh," Ruby sat down on the bench next to Jaune, "then what are you doing?" she asked, eyebrow raised.
Jaune looked out at the courtyard, "Trying to find a date to the dance, forgot that for girls to like you, you have to have something to like."
"What do you mean? You're Jaune Arc, one of the friendliest people at Beacon," Ruby stated, still seemingly confused.
"Exactly! Friendliest, as in I can make friends, not... y'know Boyfriendliest," he stumbled awkwardly over the newly created word.
There was a brief stint of silence where both parties contemplated the statement before Ruby spoke up.
"... you want to make boyfriends?" Ruby asked, wide eyed," N-not that there's anything wrong with that or anything but y'know after Pyyrha I thought you were definitely straight although I suppose you could be Bi, but then aga-"
"No! No, no I'm definitely straight." Jaune breathed in, "I meant that I'm not really boyfriend material, y'know? I mean, I'm not cool like Neptune or all buff like Sun, and my attempts at asking girls out have proven I'm not exactly all that charming. I'm basically just an average guy who's really socially awkward and able to fake confidence."
"Well if that's what you think, why don't you just ask out one of your friends?" Ruby replied, placing a hand on his thigh.
"Huh?" Jaune looked over at her.
Ruby continued, "I mean, you're not nearly as awkward around people you already know, so just ask one of those out, you have plenty of close friends who would probably love to go out with you," she glanced away after that, fiddling with the ties of her cloak uncomfortably, simultaneously hoping he did and didn't notice the emphasis she put on certain words in that sentence.
Of course being Jaune, subtle hints flew right over him and he continued his moping,
"But I'm just average, average fighter, average looking..." he trailed off.
"No you're not! You're good looking, just because you don't have muscles like Sun and you're not all bendy and acrobatic like Ren and you can't pull off blue hair like Neptune doesn't mean you aren't handsome!" Ruby shouted at him before realising how much attention she was drawing to herself and looking down at her feet. In a quieter voice she continued.
"You have really great hair and your eyes are all sparkly and blue like an ocean full of stars and glitter and stuff, and it's not like you don't have muscles, I mean it's pretty hard to be out of shape when you go to a school like this." Ruby peered up at Jaune through her eyelashes to see how he was reacting to her little impromptu speech.
Jaune's eyes were wide as he looked at Ruby,
"Really?" he asked. His seemingly positive reaction reinvigorated Ruby and urged her to continue.
"Yup! Any girl would be lucky to go out with someone as awesome as you," she paused remembering his other comment, "Besides, there's no way you could be an average fighter, you have to be above average to even get into Beacon in the first place."
Jaune laughed awkwardly at that, he still hadn't told anyone other than Pyrrha that he had lied his way into Beacon, maybe one day he would, but for now there were other issues he had to solve, starting right now. He stood up and posed confidently, puffing out his chest before turning around to Ruby.
"You're right! Meet me tomorrow, since it's the weekend we'll have plenty of time and I gotta prepare some stuff for this," Jaune proclaimed.
"Huh? What? We?" Ruby was confused by this sudden statement, Jaune wanted to meet her on a Saturday? Like a date? But he would've asked if it was a date, or would he? She didn't really know anything about how dating worked other than what she had read in some of those books Blake had hidden under her mattress and what Yang had told her from her few previous relationships. But he said meet, like a meeting about what? She was pulled out of her panicked thoughts when Jaune gave an answer.
"Of course 'we', I'm going to need help so I'm assigning you the position of my official Romantic Advisor!" Jaune paused and his confident pose slumped a little as he looked Ruby in the eyes.
"I-I mean, uh, if you don't mind..." He mumbled, not realising Ruby was busy gazing into his eyes until it had been five minutes and she still hadn't replied
"Ruby?" he shook her shoulder and she snapped awake from her trance, she really did like those eyes.
"Uh, oh, sure I'd love to help. Who knows, maybe your future date is closer than you think," she answered, unconsciously moving closer to Jaune.
Jaune's confident pose returned and he hugged the short girl, causing her to enter a brief state of mental freefall.
"Meet me at that coffee place, you know the one near the dust store?" he asked, receiving a nod in reply from the dazed girl.
"Great! Thanks Ruby, I really don't know what I would have done without you." Jaune released Ruby and she recovered, deciding she needed to stop getting distracted she replied.
"You'd probably still be striking out with random girls that walk by," she smiled jokingly.
Jaune rubbed his neck awkwardly, "Heh, yeah probably. But hey I should go prepare that stuff I mentioned, seeya tomorrow yeah?" he said while walking away backwards.
Ruby nodded and Jaune waved his goodbye as he turned and headed toward the dorms. Ruby was going the same way, but she decided to wait on the bench for a while before following in order to process what had just happened.
Yang had told her she should just find Jaune and hint that she would really like to go to the dance with him. With the defeat of the White Fang, everyone had returned to a much more normal state and most people's focus switched back to school and their personal lives, and with all their new free time not spent investigating crime syndicates teams RWBY, JNPR, SSSN and occasionally CFVY spent much more time hanging out with each other.
As tends to happen in friend groups, people began picking favourites and smaller groups and pairs from different teams split off into their own friend groups. Blake and Yang seemed to get on rather well with Fox and Coco and Sun eventually joined in when he finally got together with Blake. Weiss and Neptune spent more time together with Sage and Scarlet showing up from time to time and the strangest of all being Ren and Nora getting along very well with Yatsuhashi and Velvet.
This of course left Ruby and Jaune, and Pyrrha of course but after the breakup she began spending more time with a boy from Atlas leaving only Jaune and Ruby to become closer and closer, eventually leading to Ruby developing a crush on the knight boy.
That was two months ago, and it had only gotten worse, she had thought her speech about how generally awesome she thought he was would get him to finally realise this and hopefully lead to him asking her to the dance. Of course it failed.
"Was I too subtle?" she whispered to herself as she stood up to head back toward the dorms.
Yang was laughing, Ruby had just finished telling her what had happened and Yang had burst into laughter at her expense. Thankfully Blake and Weiss were nowhere to be found so at least she was only a third as embarrassed as she could have been.
"Romantic Advisor? Really? That cannot be true, I refuse to believe that Jaune appointed youas his 'Romantic Advisor'." Yang began to calm down though the occasional giggle still slipped through.
"I know. Oh Yang I don't know what to do," Ruby pouted, she felt Yang's hand ruffle her hair and looked up to see her sister smiling at her.
"Just do your new job sis," Yang stated causing Ruby to raise her eyebrow, Yang sighed exasperatedly.
"Advise him that you would be his best choice, simple" She rolled her eyes.
"I can't do that!" Ruby lay down on Blake's bed where she and Yang were sat as the door handle turned.
Weiss and Blake walked into the room, halting when they saw the sisters on Blake's bed. Yang looked up from Ruby's pouting face to the pair that had just walked in and asked,
"Where were you two? Actually, doesn't matter, better question, you two have boyfriends right?" She looked back and forth at the girls
"Yes?" Weiss replied, suspicious of the seemingly random question.
"Great! Then you can totally help Ruby right?" Yang asked.
"Sure," Blake replied in her usual monotone, "what with? I'm assuming something dating related since you asked but I didn't know Ruby was dating anyone." She looked up at Ruby who was now sitting up and staring at her sister.
"Yang, no." Ruby commanded, not wanting the other two to know about her crush, or her embarrassing new job title.
"C'mon Rubes, were all friends here. It's not that bad, you should be proud of your new position," Yang replied, barely holding in a snicker.
"Wait," Weiss interjected, "Ruby has a job, really?"
Yang snickered again, "Oh yeah," She pushed Ruby back as the younger girl struggled to stop her sister revealing her secrets, "You are looking at 'Ruby Rose, Romantic Advisor'."
"What?" the two other girls replied simultaneously.
"For who?" Weiss asked, wondering who would be dense enough to have Ruby give them relationship advice, her mental question was answered seconds later when Yang, still holding off Ruby, gave it.
"Jaune," Yang took a moment to look at their disbelieving faces before continuing, "Apparently our little Ruby went there to try and be his date and left promising to help him find one." Yang finished with a laugh.
"Yaaaaaaaaannng," Ruby whined, "you said you wouldn't tell."
"Look Ruby, they'll totally help you way more than I could, you know I'm not great with all that mushy romance stuff, these two have actual relationships!" Yang exclaimed, trying to make Ruby feel better about having her personal life put on show for her whole team.
"We'll try," Blake said, placing a hand on Ruby's shoulder and smiling down at her kindly, "Right Weiss?"
"Of Course! No partner of mine shall go dateless, especially when I can do something about it!" Weiss answered dramatically before peering down at Ruby and smirking, "Really Ruby? Jaune?"
The red girl groaned in reply hid her head in a pillow, "Can you just help me?" she spoke into the pillow, muffling her voice. She got laughter in response and the three other members of team RWBY gathered around their leader. Sitting next to her, they began to talk about what Ruby could do to gain the leader of JNPR's attentions.