: How do we know if a dialogue sounds unnatural without asking for feedback? I wrote a dialogue, but I am not sure if it sounds natural. I try to keep dialogue super simple so that it doesn't

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Without feedback from other people, the best way would be to read your dialogue out loud... or even the whole scene or chapter to better fit it in the context in which it was written. You could use a text to speech program to read it to you instead. Hearing the words can help internalize what we've written. It can make it easier to spot problems we might have missed after many "silent" edits.

You could also try writing different versions of the dialogue and compare them to see which one flows better.

Still, sometimes we do need new sets of eyes and ears, people who are not close to our stories. Feedback is highly valuable.

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Your goal here is to engage your intuition in ways that will help you assess your own, written work. (Everything in this answer applies to your dialogue, but also to all your writing in general).

Our intuitions sometimes work in surprising ways. You can get to understand this process to some extent, but never completely, so it's good to 1) have some standard tricks to use, but also 2) try new exercises on a hunch, to discover what works for you.

Compare this to how we communicate to the reader. For instance, "show don't tell" is all about engaging the intuition. "Telling" provides some information directly, requiring very little processing on the reader's part. So, the reader's intuition is not engaged. "Showing" provides this information indirectly, often subconsciously, and the reader's intuition is engaed in order to process it. In the latter case, the information sinks in more deeply, and is subjected less to disbelief caused by conscious awareness that this is just a story.

How can you do something similar for yourself?

Start simply by reading your dialogue out loud (and, for that matter, your entire story): read it to yourself. Next, you may not have a writing group, but find a willing friend and read it to them--you don't even need to ask for feedback.

I found reading to a friend to be radically different from reading out loud on my own. As I read to the friend, my intuition was suddenly engaged, I was "identifying" with the "experience" of my listener, and suddenly I was much more critical of my words, more sensitive to the effect they would have on an audience.

There are more tricks.

Use a TTS programme (text to speech) to have your computer read your text to you. This engages your intuition differently, and provides you with a different point of view of your work.
Post a chapter of your writing online. With the work being "out there", suddenly you yourself will see it differently. Re-read it on the website where you posted it.
Read a chapter you have written, trying to select a single page or paragraph that you will read to a friend or post online for critique. Thinking about what selection to make will engage your critical thinking and give you a new point of view.
Write a pretend sales pitch to a publisher, where you praise your own writing and provide a sample of it (I'm not saying this is actually a good way to pitch writing to a publisher). Incidentally, I myself hate sales, so it is painful to do this. But, once more, new point of view, new way to engage the intuition.
Write a story in a story. The characters in the "outer" story tell eachother an "inner" story. Have different characters in the "outer" story respond differently to the dialogue in the "inner" story.
Re-write your text, changing between 1st and 3rd person PoV, but using the same dialogue.
Get a friend to read your text to you.

Having said all this, getting feedback is extremely valuable. If at all possible, try to do that too, when you and your writing are ready to move on to that stage.

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I often stumble apon the same issue.

+1 for Cyn, because reading the dialog out loud is one of the tools you can and should use to make it sound more natural.

If I get the feeling that something might be off I read the dialog completely without any dialog tags or actions in between and ask myself the following:

Is the said building up logically?
Can I differ between the involved characters simply by the tone of the dialog?
Would I feel uncomfortable if this was a real conversation and my buddy would answer me in that way?

This list makes no pretence to be complete, but I hope you get the idea of what I'm trying to say.

Another thing you can do is - in regard to your example - to stretch the dialog a bit by action in between. You say

I am not sure, but laughing and then saying goodbye immediately sounds unnatural

and you are right. If this was a real conversation I would be more then a bit irritated. But if you put a little break in there it becomes automatically more natural (note: English is not my prefered langugae for prose so please be gentle)

"Haha, yeah right. I'll be around the neighborhood if you need me." He sighed deeply and the two of them for a while sat silently side by side, gazing into the nightsky. "I might have to leave by the end of the month", he claimed as he stood up. "So call me if you want to hang out, okay?"

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Sometimes you don't.

You can (and should) read it out loud to yourself. But there really isn't a substitute for having other people listen to it. In my critique group, we read a portion of our piece when we present. Sometimes I find myself cringing at my dialogue. Stuff that sounded so good in my head. Other times it sounds okay to me but my fellow group members disagree.

If you don't have a critique group, rope in family and friends. If that doesn't work, try some open mike nights (for creative writing, not songwriting). Even if no one gives feedback, the act of reading it out loud can tell you what you need to know. Do you stumble over it? Are you embarrassed to say it? Or does it bring up emotions? the right ones?

If you can't find places to read your work, read it to yourself. Or tape yourself reading it then listen to the tape. Follow along on your printout and circle anything that sounds off.

There's no shortcut. Sometimes we can do all this in our heads but, more often, we just think we can.

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