diff --git a/Lib/textwrap.py b/Lib/textwrap.py
--- a/Lib/textwrap.py
+++ b/Lib/textwrap.py
@@ -73,22 +73,36 @@ class TextWrapper:
     for x in _whitespace:
         unicode_whitespace_trans[ord(x)] = uspace
 
-    # This funky little regex is just the trick for splitting
-    # text up into word-wrappable chunks.  E.g.
+    # Word + punctuation
+    word_punct = r'[\w\!\"\'\&\.\,\?]'
+
+    # This funky little regex is just the trick for matching word-wrappable
+    # chunks one at a time in a text.
+    # E.g.
     #   "Hello there -- you goof-ball, use the -b option!"
-    # splits into
-    #   Hello/ /there/ /--/ /you/ /goof-/ball,/ /use/ /the/ /-b/ /option!
-    # (after stripping out empty strings).
-    wordsep_re = re.compile(
-        r'(\s+|'                                  # any whitespace
-        r'[^\s\w]*\w+[^0-9\W]-(?=\w+[^0-9\W])|'   # hyphenated words
-        r'(?<=[\w\!\"\'\&\.\,\?])-{2,}(?=\w))')   # em-dash
+    # matches into
+    #   /Hello/ /there/ /--/ /you/ /goof-/ball,/ /use/ /the/ /-b/ /option!/
+    wordmatch_re = re.compile(
+        r'('
+        # any whitespace
+        r'\s+'
+        # <space>--<space>
+        r'|(?<=\s)-{{2,}}(?=\s)'
+        # <word | punct>--<word>
+        r'|(?<={wp})-{{2,}}(?=\w)'
+        # word, possibly punctuated or hyphenated
+        r'|\S*?\w{wp}*(-\d\w+)*([^-\w\s]+|-(?=\w)|--+([^-\w]*$))?'
+        # catch-all for other stuff, until next space
+        r'|\S+'
+        r')'
+        .format(wp=word_punct))
+    del word_punct
 
-    # This less funky little regex just split on recognized spaces. E.g.
+    # This less funky little regex just matches on recognized spaces. E.g.
     #   "Hello there -- you goof-ball, use the -b option!"
-    # splits into
-    #   Hello/ /there/ /--/ /you/ /goof-ball,/ /use/ /the/ /-b/ /option!/
-    wordsep_simple_re = re.compile(r'(\s+)')
+    # matches into
+    #   /Hello/ /there/ /--/ /you/ /goof-ball,/ /use/ /the/ /-b/ /option!/
+    wordmatch_simple_re = re.compile(r'(\s+|\S+)')
 
     # XXX this is not locale- or charset-aware -- string.lowercase
     # is US-ASCII only (and therefore English-only)
@@ -159,10 +173,18 @@ class TextWrapper:
         otherwise.
         """
         if self.break_on_hyphens is True:
-            chunks = self.wordsep_re.split(text)
+            wordmatch = self.wordmatch_re
         else:
-            chunks = self.wordsep_simple_re.split(text)
-        chunks = [c for c in chunks if c]
+            wordmatch = self.wordmatch_simple_re
+        i = 0
+        n = len(text)
+        chunks = []
+        while i < n:
+            m = wordmatch.match(text, i)
+            assert m is not None, repr(text[i:])
+            c = m.group(1)
+            chunks.append(c)
+            i += len(c)
         return chunks
 
     def _fix_sentence_endings(self, chunks):