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I am not asking you to tell me to keep my sentences less than 20 words long because I am determined to write some really long sentences. What I want to know is how to avoid sounding unnatural. Do I have to avoid certain kinds of words, words of a certain length, etc? Is there something about the phrasing itself?

I guess by natural I mean smooth and pleasant. Rhythm is another thing, but before I deal with that fully, I need to make sure I can sound natural.

I noticed that when I wrote something, because I used the word, "regarded", it sounded awful to me.

Does anyone have any idea what I am talking about?

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    You will have to provide some more details, mate. For what are you asking ? Target audience ? What genre ? smooth and pleasant would mean different things to different people...You can't expect us to guess those... – user96551 Oct 16 '16 at 7:13
  • This has nothing to do with writing a book @user96551. Guido, are you a native speaker, or a non-native asking for help with sentence structure? – Featherball Oct 16 '16 at 7:17
  • I am a native speaker. I am talking about this: How do I write smooth flowing sentences? I know that phrase-length and clause-length control rhythm, as well as accent and things like parallelism, but if you can give me a basic principle for making a sentence flow smoothly, what would it be? – user10405 Oct 16 '16 at 7:36
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    I provided an answer with plenty of points, but I'd just say: just don't put unnecessary words in. @GuidoArbia – Featherball Oct 16 '16 at 12:41
  • Just reading the question and these comments alone, my first reaction would be that you are overthinking the technical side of writing, and over-criticizing what you write. Is it possible that you are doing this? – Thomas Reinstate Monica Myron Oct 17 '16 at 22:22
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All of my answers are ludicrous and too long, so you can skip to the conclusion at the end if you don't want to read.

Introduction

I think it can be quite easy to make sure your sentences sound gorgeous and flowing, perfect and natural. I think it would be a good idea to begin by saying this: you do not have to avoid any words or phrases, as long as they fit your style and tone. You should use words that fit the genre and target audience of what you are writing. Be consistent with these and use them throughout the piece, as tonal shifts can ruin your work.

My advice and points

Here are some notes on words however, that you may want to pay attention to:

  • Avoid repeating words like and, which, because and other connectives in a sentence. Also avoid repeating subject pronouns constantly.

For example, let us look at the following sentence:

I ate bread and drank milk, and then I went to bed and got to sleep instantly.

This sentence is very poorly written. It uses and three times. Your English teacher will tell you that repetition can be a good technique... But in this case it definitely isn't. It makes your writing appear sloppy, unprofessional and bad. Also, pay attention to the style I wrote this in. I wrote this as if it were a diary, or blog, or retelling of a normal event. Because this is contemporary it would be fine for me to say got to sleep or went to bed . If I was writing fantasy, I would perhaps refrain from these terms which in my eyes, seem too contemporary. Perhaps if you were writing fantasy set in a cliche medieval England setting, you could say fell into a slumber or snagged my eyes shut. But of course, you wouldn't use these terms just around the house. They're very stylistic and revolve around genre and tone very much.

I would rewrite the sentence like this to avoid repeating and and I.

After enjoying bread and milk I went to bed, falling asleep instantly.

We can see that the first part is all a main clause and I am just adding falling asleep instantly as extra information without repeating anything unnecessary.

  • Try to use different sentence lengths

Okay, I bet you already knew this, but I'll point it out anyway. You must vary your sentence lengths if you want to have good sounding sentences. Part of making sentences sound good depends on the passage they are in. Of course varying sentence lengths can make for epic cliffhangers:

Go now, she thought, and closed her eyes; and when she opened them again she found she was alone. That was how she learned to do it. ~ Justin Cronin... The Passage.

I swear, that sticks in my head. I can never unsee some of the things I read in that book. It makes for a great example of sentence length being used to create a cliffhanger here.

  • Don't use too many interjections

In your narrative not your dialogue try not to use too many interjections. This'll remove a lot of formality, and also make the piece appear like a diary entry. Unless you want your narrator to be like this, don't write something like the following:

She put some socks on; I guess she was cold

The I guess is completely unnecessary here and the narrator doesn't really need to say it.

  • Understand English grammar and PUNCTUATION!

This is totally self explanatory. Its so self explanatory I won't bother to extend my explanations even more on it. Good grammar and punctuation = instantly clearer meaning, instantly better sentences, hugely engaging passages. Learn about clauses, stressed syllables, trust me it'll help.

Conclusion

  • Avoid repeating words like and, which, because and other connectives in a sentence. Also avoid repeating subject pronouns constantly.

  • Try to use different sentence lengths

  • Don't use too many interjections

  • Understand English grammar and PUNCTUATION!

  • Pick a style and be consistent with it throughout the entire thing. Ensure that every word is good for your genre and audience.

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While we may be able to break down a successful long sentence analytically, I'm not sure that this is going to help you write them fluently. Language is about rhythm and balance and how the reader's focus is directed. I think that has to come from training your ear.

The best way to train your ear is to read writers who are noted stylists. You don't necessarily have to aspire to the same facility with languages as the greats, but if you want to develop the kind of ear for language that will let you write a long sentence with fluidity and grace, you need to immerse yourself in that kind of language, in the works of writers who do it superlatively well. And read with attention, roll the language around on your tongue and get the taste of it. You train your ear by immersion, but by purposeful and attentive immersion.

Also, consider that a good long sentence is one that is naturally long. You probably will not notice how long it is as you write it, nor as you read it. Artificially long sentences are always going to sound awkward and contrived. Naturally long sentences are going to result from saying something sophisticated or nuanced, something that demands more that a few words to tease out it subtlety. So I would suggest that a determination to write long sentences is misplaced. Rather, determine to write something with the kind of subtlety or precision that sometimes requires long sentences, and don't worry about whether the sentences that result are long or short.

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A simple, semi-reliable test of whether your writing sounds natural: Read it out loud. Does it sound natural?

A less simple but more reliable test: Hand it to someone who has not read it, and ask them to read it out loud. Do they stumble as they are reading it? Does it sound natural?

I listen to lots of audiobooks. Even the most professional readers stumble sometimes (and some of those stumbles make it through to the published audiobook). Inevitably, when professional actor or audiobook reader stumbles, it's because the text is awkward in some way.

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Lythric has a good start. I would add an old junior high teacher's advice. Don't worry about grammar or punctuation, if you can read it aloud, it is English. Then you can do the old chestnut, all writing is rewriting. Why are you writing in such a way? Does it advance your story, or point? Are you guilty of style over substance? Find a good reader. Put a snippet or chapter out to a local or online authors group.

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