diff --git a/Lib/textwrap.py b/Lib/textwrap.py
--- a/Lib/textwrap.py
+++ b/Lib/textwrap.py
@@ -79,10 +79,22 @@ class TextWrapper:
     # splits into
     #   Hello/ /there/ /--/ /you/ /goof-/ball,/ /use/ /the/ /-b/ /option!
     # (after stripping out empty strings).
+    word_punct = r'[\w\!\"\'\&\.\,\?]'
     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
+        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.
     #   "Hello there -- you goof-ball, use the -b option!"