using System; using System.Collections.Generic; using System.IO; using System.Linq; using System.Text.RegularExpressions; public class Test { public static void Main() { var text = "12\"The world... 13The end 14\"I have 16 years 15Kiss me"; Console.WriteLine(Regex.Replace(text, @"\s+(?=\d+[^\s\d])", "\n")); } }