Making a game plan is actually pretty smart when it comes to these things. As someone else mentioned, you basically just balance brevity with detail, while trying to create an easygoing tone. Here are a few restrictions that I unconsciously came up with that tend to make for smooth conversations where the girl doesn't lose interest. I'm no guru, but I tend to get like 3/4 of the girls I message to imessage so I think I at least have the texting part down.
And remember to think of these as restrictions that lead to better expression of your true personality, a la the 5-7-5 restriction of Haikus:
That's basically my "game plan." Hope this helps!