Hey, Lancaster shippers. Got a minute?

Listen, for what I've seen, you understand romance better than I do. But, off the top of my head I would say you can work around their hug in volume 6. Not necessarily using the scene per say, but sort of having Jaune realizing Ruby is more special to him than he thinks by having them split for a while in a dangerous situation. You can also work around her inspiring him to be better like she did in volume 1 and volume 4.

I don't go here, but isn't the whole appeal of Lancaster their easy camaraderie and inherent understanding of two awkward nerds thrust into positions of leadership gradually realizing that their friendly rapport is not, in fact, platonic? You don't necessarily need a Big Dramatic Shift to fall in love with your best friend.

Alternatively, severely injure one of them. Jaune if you don't want to be a hack.

Sudden injury or disappearance can obviously make someone realize subconscious feelings or want to appreciate what they have and take that step before its too late. But for the sake of being different, perhaps a change in perception.

Jaune seeing Ruby is a different light, and being introduced to a new side to her might garner a sort of reaction to push beyond friendship.

Point being that perception can influence feelings. An encounter in an unfamiliar situation could make Jaune interested in Ruby as a woman, or seeing Ruby interact w/ kids might show him a glimpse at Ruby as a mother. Maybe during the time traveling together and seeing a more vulnerable Ruby might make Jaune's feelings towards Ruby develop. Maybe Ruby herself making her romantic feelings toward him known, can inform Jaune of a side of Ruby he had never considered that existed. Which would prompt him to examine how he feels about Ruby, and how this "new" side of her changes their relationship. Maybe the larger group being separated and Jaune having to step until the position Ruby would usually fill. Being responsible not just for his own team, but much more. Current Jaune having matured and grown both as a person & huntsman, getting to be in the "hero" role he used to aspire to, realizing the weight of the reality. Coming both to a greater appreciation of Ruby & an even deeper desire to support her, not because they're friends, but because he loves her.

Well if we're talking about an early RWBY timeline plot point, then expanding upon Jaune and Ruby's talk during the Jaundice arc (ha!) might be a good tipping point for Jaune for seeing Ruby in a more romantic light.

I wouldn’t consider myself even a decent writer when it comes to romance, but I figured that I may as well give something since there aren’t many Lancasters on here.

1. Near death experience. This one isn’t original, but that doesn’t necessarily mean it’s bad. Ruby could easily be put into some sort of danger, but that happens a lot (there is a reason for that though, people like “knight in shining armor” stories). If you want some originality, you could have Jaune almost die in some big fight, and afterwards he starts putting his life into perspective. He realizes that a Huntsman’s life usually doesn’t last long, so he decides to start enjoying it while he’s still alive, which leads to him starting to think more about romance and, in turn, Ruby.

2. Someone plays matchmaker. This could vary greatly depending on how lighthearted or serious you want to make it. It could range from Yang and Nora coming up with some elaborate scheme, or Jaune having a serious talk with Ren about his feelings like he did in V2 (except now Ren could give Jaune advice based on his experiences with Nora). Only problem here is it may be hard to write this in a way that makes Jaune fall for her rather than him just realizing that he did. Not a terrible idea, but it’ll probably work better if it’s combined with a different way to make Jaune initially fall in love.

3. Work with the friendship and similarities. The most appealing thing about Lancaster is how many similarities Jaune and Ruby have and how close they are because of it. An idea I had for my own fic is he’s up way later than everyone else stressing over making a plan for something the group is trying to do. As he’s losing his mind over not being able to come up with a good enough plan, Ruby shows up offering to help, saying that it’s their shared responsibility as the leaders. Jaune realizes that Ruby is the only one who really gets him, and boom. He falls for her (except I’m sure you can write that scene way better than I did). And there’s tons of different things you can do depending on how serious and whether you want it to be an immediate decision on Jaune’s part. Maybe they check the news and see that a sequel to a video game they like came out, but they can’t play it due to their present situation so they promise to play together immediately after the world is saved, or maybe they’re both talking while being wallflowers at a social gathering (like a festival in a Vacuan village or something), mirroring V2.

4. Make a conflict. Currently, Jaune and Ruby haven’t argued over anything, but that doesn’t mean they agree in every single thing. If your story is set during the Atlas arc, then you could write about their differing views about leaving Mantle. Iirc, we never saw how Jaune thinks about Ironwood’s plan or about leaving Mantle, so you have some freedom there. Maybe Ruby wants to make sure she saves everyone, but Jaune would rather save as many people as they can before cutting their losses in order to keep the Winter Maiden out of Salem’s hands. Ozpin is another pretty easy topic. Maybe Ruby is willing to trust Oz to an extent, but Jaune wants to make sure he has nothing to do with making decisions in order to avoid him leading anyone else to their deaths. Trick here is to not make Jaune seem antagonistic, and like he actually has a good point and a reason for thinking the way he does. An easy way to do this would be to have Jaune simply explain his thought process and offer a decent plan to pull it off, or have some others agree with him so it’s not Jaune vs. Everyone.

One thing I would like to add about your point about Ruby being a flat character, I wouldn’t worry too much. If you want to have Jaune fall for some quality or qualities about Ruby, then you don’t need to use the excuse that Ruby changed as a person (because she didn’t). Instead, you can say that Jaune changed. V1-3, his social status was so low, and combined with his experiences with the way Weiss treated him, one could reasonably argue that for most of his time at Beacon, Jaune didn’t even think anyone could like him that way, so he never really developed strong feelings for anyone until Pyrrha practically confessed. V4-6, Jaune was so consumed by guilt and a lust for revenge that love was the last thing he would be worrying about. V7 has Jaune start piecing his life back together, so maybe he starts thinking about that kinda stuff more.

There’s some more ideas I have, but they’re more of just specific events that don’t really fit a broader category, so I’ll just leave them out (unless you want me to go into more detail). Overall, I’m just gonna say this: if you have an idea you like, write it. Even if it’s not the most original or you think it’s not the most groundbreaking idea, just start writing and go with it. Writing is meant to be fun, and if you’re picking ideas that you don’t really love because someone on the internet said they might be better, you probably won’t be having as much fun writing, and that scene, even though it may have been a better idea, will probably turn out rather lackluster because of it.

Maybe appeal his desire to protect. Jaune's main goal is to keep his friends safe but Ruby is a "risk it all" kind of hero. You can easily create conflict with this and use it as the main drive for a growing romance while giving them character development. It can all begin with Ruby getting injured, trying to sacrifice herself or just pushing herself too hard to make Jaune become wary of her. Maybe she can steal a line from Pyrrha to trigger some PTSD like "You know what my silver eyes mean. This is my destiny."

They are all set for a slow burn kind of love, but I get your point, most lancaster stories are about Ruby falling for Jaune or Jaune just realizing that he is in love with her, but there are few who dare to get Jaune to fall for Ruby for "something new".

It it were me I would get Ruby to show a more mature side of her and that could get Jaune's attention, it would contrast nicely with their current "best buds/dork leaders" dynamic.

The Atlas arc made wonders on showing a more grown up side of Ruby with her change of appearance, now we just need her personality to chatch up to her appearance.

It could be a Ruby more consious of the phisical closeness that she shares with Jaune when they interact (like that hug outside of the dust mines where by their heights Jaune was practically carrying her).

I don't know, something that makes Jaune realice she is no longer a kid anymore, not necessarily sexual tho.

Since you seem to have gotten plenty of good help from other users here, I have nothing more to add to this.

However, I would like to extend an invitation to the RWBY Nook discord server, a RWBY writing server made by writers, for writers. We'd love to have you!

You've gotten some good advice. I strongly agree with the separation or threat of loss making Jaune see her in a new light, review his feelings towards her. Also, someone playing matchmaker. Since others have already covered them, I will not waste anyone's time by writing more. However, I would like to add three more possibilities:

#1. Someone else shows a romantic interest in Ruby. As much as Jaune might like to think he's fine with it, he may not be. Again, seeing someone else expressing a romantic interest in her could make him re-examine his feelings towards her.

#2. Ruby hits rock bottom and Jaune is there for her. I know that there's a fine line between support and creepiness, but I could see Ruby coming close to giving up the quest, or perhaps the party is separated again. If most of her friends and family are separated from her again, she could turn to Jaune for comfort and that comfort could change to something else.

#3. They find themselves playing the part. This would be more of a playful sort of thing, but remember when they got their huntsmen licenses and she asked if she could go "under cover"? What if she and Jaune go on a recon mission, in the populace, and act the part of boyfriend and girlfriend in order to blend in. The two of them acting like they're a couple could get them to wondering why they aren't really a couple.

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So I personally like the idea of fear of losing Ruby being the catalyst for Jaune realizing his feelings for her. Maybe have him freak out that something is going to happen to Ruby only for Ren to reassure him that RWBY will be fine. Nora could be on the sidelines face palming at the obvious miscommunication. You could maybe have Jaune draw parallels between Ruby and Pryhha with both of them willing to put themselves in danger to be a hero. This could create some drama with Jaune pleading with Ruby to not do something dangerous and possibly give Ruby some depth if you come up with a good enough reason why she thinks it needs to be her.

There’s also the cliche of one of them being hurt. I think this can be effective if you remember why it’s a cliche.Being hurt likely means someone caring for you. A Lot of people love the idea of being cared for and it can be very intimate. Also in stories the physical vulnerability of injury could also pave the way for emotional vulnerability. Jaune could realize his feelings for Ruby by allowing himself to completely open up and be vulnerable with her.

I know this has been mentioned here already but I suppose Ruby would get captured by Salem and Jaune would constantly be worries about her. Once they do save her, maybe Jaune starts to realize how much Ruby means to him. You could even have Yang or Nora address it afterward.

A suggestion I don't think I've seen here: common grief.

For example, have them go on a mission with a third character they both love, such as Weiss - or another less important one, but it won't be as impacting -, and then have that character die tragically.

The way I did it in my fic is I made Jaune know Summer as some kind of friend/mentor and when she died I made it so Ruby and Jaune are unable to mourn properly. So when they meet each other at Beacon they can talk about the specific aspects of Summer they've personally seen, which finally provides them closure and makes them very close in a very short time.

Just have Cinder almost kill her, that seems to happen to every single romantic interest of his^/s