Imagine you have two characters talking about past events. Then you want to have a flashback. Does this format work. "What happened in New Orleans" asked John. Jane frowned. "I'll tell you everything," she said. Then another chapter: CHAPTER 3: New Orleans, a few weeks earlier. (Is this the correct way of writing the start of a new chapter?) Jane arrived in New Orleans on a rainy day. ..........
I think you could handle that transition as a section break within the chapter, rather than starting a new chapter.
You could write it in Jane's voice as dialog, use a chapter break, continue without a chapter break (A few weeks earlier, Jane had encountered a grizzly bear on Bourbon street...), start a new chapter, and other ways that I haven't thought of. One of the cool things about being the story teller is that you get to suit yourself about how you tell the story. Rumer Godden switched between past and present in the same paragraph at times and did it beautifully. I highly recommend reading Five for Sorrow, Ten for Joy not just because it is a fine book but because of the interesting rhythm of her writing and arrangement of events.
If you plan on telling it in third person, I'd go with a chapter break but if it's natural first person dialogue, I'd just use a section break. By the way, you generally don't need a dialogue tag if you have an attribution/action beat right before the line. So: Jane frowned. "I'll tell you everything." she said.
I'm just newbie at all this, but I've started a "recollection" chapter this way: Lieutenant jg Bowman stared out the window of the lighter at the clouds below. It reminded Kelly of her descent to Aurega Central three months ago. I then continue to relate events leading up her return. In fact, most of the chapters in this section are similar recollections of 'how they got there.'
I'd probably go with something like this (I'm changing Jane's name, it's too close to John): "What really did happen in New Orleans?" John looked intently at Sarah. Her eyes focused on the distance. * * * Rain was pelting the cobblestone streets relentlessly. Faint sunlight glinted from wrought iron along the balconies. They would be closing in soon, but she... It's a new scene, so you give a setting, a brief description of the surroundings and the mood (cobblestone streets and wrought iron railings, which give strong French Quarter vibes, with hard rain establishing a mood), and you just go right into the flashback. No need to say how long ago it was, if that's important you could give it in the dialog preceding the flashback. Readers will understand it's a flashback because of the shift in place and scenery and weather etc. And when you return to the scene from before that will be clear as well, because they're standing where they were before talking to each other. I think you can cut directly into the flashback since he just asked her what happened. The little zoom-in on her eyes is the cue that we're moving into her head now, this is the flashback. You don't need any more devices to establish that. I used the three asterisks as an in-chapter break to make it clear something has changed. If it's a long flashback make it a separate chapter. If I had said "She looked into the distance" that would be the written equivalent of a mid-shot, showing her head and upper torso, or maybe a moderate closeup on her face, but because I said "her eyes" it becomes an extreme closeup, just on the eyes. And the fact that she focuses on the distance shows that she's thinking about something not in the here-and-now, she's already going into the flashback. I also used a very subtle tense shift at the beginning of the flashback, just for the first sentence—rain was pelting rather than rain pelted. I don't know what that tense is called, but it's a little different. We're still in a form of past tense, but it seems in-progress because of the 'was pelting'. Then the rest of the flashback returns to normal past tense. It's also a change from dialogue to action, with a female character (she). All this together makes it clear it's her flashback. I don't even think it's necessary to say Sarah at the beginning, it's clear from the context.
Looking at what I wrote now, it might need just a little more transition into the flashback. Maybe: "What really did happen in New Orleans?" John looked intently at Sarah. Instead of answering she looked past him into the sky, her eyes focused on the distance. * * * Rain was pelting the cobblestone streets relentlessly. Faint sunlight glinted from wrought iron along the balconies. They would be closing in soon, but she...
What if I have a flashback within a flashback and then go back to original time? How can I make sure the reader doesn't get confused? Sara stopped and asked John about his adopted daughter. His mind slid back to the time when John had found Naomi in an orphanage. *** It was a snowy February day. After much deliberation John had decided to adopt a child from the orphanage. In there, he came across a girl with deep blue eyes. He stopped, staring into her eyes. "John, what brings you here?" she asked. John was stunned at the mention of his name. **** (a flashback about Naomi's background) Naomi's life had been quite a roller coaster. XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX (imagine this continues for one page.) **** (back to that Snowy February day) John stepped closer towards Naomi. "How do you know my name, young lady?" Do I need to say we're back to that February day and separate it from that Naomi's background part?
A flashback inside a flashback seems like too much to me. Personally I wouldn't try it unless I had a really good reason and felt like I really understood how to pull it off.
This might be doable if you just used a paragraphs or two as exposition on Naomi (like how she ended up there, etc.), which technically wouldn't be a flashback in my opinion. If it goes on for a page, that's closer to a flashback, especially if you use a lot of showing versus straight telling.
Looking at what you wrote I would just change it a little so the first part isn't really a flashback but the transition into the flashback. One way to transition is to have the memory spurred by something—a sight, a sound, a smell—something that triggers it. "So, tell me about Naomi." He tilted his head back and gazed into the sky. It was some moments before he spoke. "It's almost the same. The sky I mean. Some days it's almost the same..." Sarah leaned back and put her legs up on the chair. "The same?" She idly stirred her coffee, waiting for a response. But he wasn't there anymore. He was with his wife, in that dingy little playroom at the orphanage. There were toys, but none of the kids were playing. They just sat around looking forlorn and lost. He was getting a bad feeling, thinking adoption isn't really the right thing for them, when he saw her for the first time. The little blonde girl that would change his life. The eyes as deep and blue as a summer sky with no clouds. When you're writing about someone's memories you can jump all over the place, it doesn't have to be structured liked flashbacks within flashbacks. Memories just jump around like that, linked by association. So you can say things like— Her eyes got darker over the next few weeks, they were never the same again. But whenever he thought of her that's how her eyes always looked. When she was in high school, when she went to college, when she came back. She always had those angelic eyes. Once you've established that memories have different rules than standard storytelling, they can flit all over the place. Then you're free to jump around and say whatever you need to say. Just make sure it's motivated by what the readers need to know and you can skip years forward and then years back in a single sentence if you want to. The same girl who broke her mother's favorite vase when she was four, and brought home a stray cat when she was twelve. That kind of stuff.
