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My story has two POV characters, Delilah and Jack, who start separate and meet ~ 1/4 of the way though. Delilah's story starts several years before the Jack's and is the entire reason he even has a story at all.

The thing I'm not sure about is, because Delilah's story starts so far ahead of Jack's, how do I structure the story so the the reader will care about both characters individually as well as their relationship once they meet, without the story being disjointed and ineffective

There's a few ideas I've thought of:

  1. Start the story when they meet and going back to the starts of their respective stories and alternating chapters following each one past the point hen they meet, to the end of the book. But I've read that en media res is often kind of boring, as readers generally prefer chronological order, and aren't invested enough to put in the effort to follow the rest of the story.

  2. Start the story when they meet and treat everything from before that point as back story, sprinkling it in as and when. That would probably be ok for Delilah, but I think Jack's character development would be better served starting sooner.

  3. Follow one exclusively until they meet, the indruce the other. I have obvious concerns with this one, for one, adding a POV character halfway though is always risky and I think both their stories deserve a share of the spotlight. Alternatively, I could completely omit one character's POV. This has a similar problem. That both character arcs would work better as a POV. Internal stuff makes up a larger proportion of Jack's arc, so it wouldn't work that well without getting in his head, but Delilah's storyline up to the meeting is more dynamic.

  4. Have their stories before they meet be two separate books and another book with alternating POV for the story after they've met. Their stories upto when they meet isn't particularly satisfying as it stands, but I'm still at the stage where I don't have many concrete ideas about what happens so it could be made into one relatively easily. However, I'd be changing to a character the reader doesn't already know, so that doesn't seem much better than the last option.

Obviously this isn't an exhaustive list of options! It's just the main ideas I've thought of and been able to research. I'd really appreciate any input you guys could give me on this! No knowing how I'm going to format the plot is one of the main things making it harder for me to push through perfectionism and actually write this damn thing!

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I think that the rule of thumb with writing holds true here, and it can be an annoying one - try something and see what sticks. You might try outlining scene by scene.

I can see the difficulty however, of how to switch between the POVs, when the second POV has a big time difference. You could always try specifically pointing out at the start of the chapter the time difference, some stories have done this well.

For some guidance on this, I recommend looking at Brandon Sanderson's novels, and how they manage viewpoints. The Stormlight Archive especially has to manage a lot of flashbacks and the most POVs I've ever seen in a story.

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There is another option, which I think has its merits.

  1. Alternate between their chapters, despite the fact that their stories are going on at different times. You can either establish what the time is in Delilah's story and what the time is in Jack's story, letting the reader have a good comprehension of when the story beats are happening relative to each other, or, mislead the reader. The latter option can bring some nice shock value, and it makes your book much more re-readable, since readers will have a new experience when reading the first quarter of the book after finding out the true chronology. Furthermore, if their stories are quite far apart in time, then this means the chapters will offer a nice change of scenery for the reader. In Delilah's chapters, you can be a bit nostalgic about whatever time her story is set in, and in Jack's chapters, you get a world more like our own.
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I'd read the novel "Holes" which features 3-4 stories with characters that don't meet, but whose actions help influence the main plot. The main story follows a boy sent to juvenile detention camp in the middle of a desert (we meet him as he is arriving). We get a flashback story to the reason why the kid got sentenced to do time in the camp, which was a series of unlucky events that is half-jokingly blamed on the family's belief in a curse placed on the boy's Great Great Grandfather. We then get a flashback to that story and learn the origins of the family's curse (he stole a pig from a gypsy woman). Later, the book also flashes back to about the detention camp's origins as a lakeside town in the late 1800s and a school house teacher's role in a scandal that resulted in the lake the town was built around drying up and the town becoming abandoned.

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