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Assuming the story itself is in past tense, normally when I go further into the past I'd use past perfect:

He had first met her at the grocery store, six months prior.

However, which is more correct when writing an extended flashback (several pages):

He fondly remembered the day they met.

He had met her at the grocery store, where they had shared a long glance at the checkout line. She had bought sixteen oranges and one single banana, something that had caught his eye at once. He had only been purchasing a pack of gum. He had been about to leave when he had noticed her self-check ding...

versus

He fondly remembered the day they met.

He met her at the grocery store, where they shared a long glance at the checkout line. She was buying sixteen oranges and one single banana, something that caught his eye at once. He was only purchasing a pack of gum. He was about to leave when he noticed her self-check ding...

My instinct is to leave the first sentence as "had met her", then switch to simple past tense. Is that strange?

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It's not strange at all. That's exactly how I would do it. A flashback of two paragraphs can take past perfect. A flashback of several pages can be in the simple past as long as you establish the time shift clearly at the beginning, and use the past perfect in one or two sentences at the beginning.

You should also clearly indicate when the flashback ends: "Now that it was summer, the watermelons took on an entirely new meaning."

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Some authors also end the flashback in past perfect, using this tense like parentheses. –  John Smithers Nov 1 '11 at 18:38
    
I'm fine with that as well, John, so long as it's clear in some manner that the flashback is over and we're now in the "present" of the story. (or the future, or another flashback, or whatever.) –  Lauren Ipsum Nov 1 '11 at 19:43
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I'd go with past, actually. If you use past perfect, there's no need to italicise, is there? It's effectively not a flashback, but just narration. Flashbacks are meant to take on an element of immediacy, of being dragged into a moment re-lived. (In fact I've actually switched to present tense for flashbacks with no reader confusion. Indicate that you're about to "remember" something, use italics...you'll be fine. Flashback is over when italics end).

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What if I don't use italics? Or do you reccomend always doing so? –  Yamikuronue Nov 1 '11 at 18:23
    
Stylistic choice. You can; you don't have to. Italics do make the flashback clearer, but for me as a reader they also change the mental voice in which I'm reading the text. That might be difficult if it goes on for pages and contains dialogue. –  Lauren Ipsum Nov 1 '11 at 19:43
    
If you're not going to use italics, you treat it as a separate scene and make it clear that you're going back in time to something. Or you simply "narrate" your memory without using the flashback device (be careful to slide this in at an appropriate time so it doesn't look like an info-dump). –  Lucy V. Morgan Nov 2 '11 at 2:14
    
I was planning to alternate past and present sections for a good chunk of the book, so I think italics will be more annoying than helpful. –  Yamikuronue Nov 2 '11 at 12:59
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