diff --git a/src/_pytest/assertion/rewrite.py b/src/_pytest/assertion/rewrite.py
index ab5e63a1e0c..aca8cf5014e 100644
--- a/src/_pytest/assertion/rewrite.py
+++ b/src/_pytest/assertion/rewrite.py
@@ -435,6 +435,24 @@ def _call_reprcompare(ops, results, expls, each_obj):
     return expl
 
 
+def _call_reprcall(callable, args, kwargs, result, expl_callable, expl_result):
+    import re, regex
+    regex_callables = {
+            re.match, regex.match,
+            re.search, regex.search,
+            re.fullmatch, regex.fullmatch,
+    }
+    if callable in regex_callables:
+        # I'll have to figure out how to deal with kwargs/optional flags.
+        pattern, string = args
+        return util._call_regex(callable, pattern, string, 0, result).replace('\n', '\n~')
+
+    else:
+        return "{}\n{{{} = {}\n}}".format(expl_result, expl_result, expl_callable)
+
+
+
+
 def _call_assertion_pass(lineno, orig, expl):
     # type: (int, str, str) -> None
     if util._assertion_pass is not None:
@@ -965,8 +983,16 @@ def visit_Call(self, call):
         new_call = ast.Call(new_func, new_args, new_kwargs)
         res = self.assign(new_call)
         res_expl = self.explanation_param(self.display(res))
-        outer_expl = "{}\n{{{} = {}\n}}".format(res_expl, res_expl, expl)
-        return res, outer_expl
+        expl_call = self.helper(
+            "_call_reprcall",
+            new_func,
+            ast.List(new_args, ast.Load()),
+            ast.List(new_kwargs, ast.Load()),
+            res,
+            ast.Str(expl),
+            ast.Str(res_expl),
+        )
+        return res, self.explanation_param(expl_call)
 
     def visit_Starred(self, starred):
         # From Python 3.5, a Starred node can appear in a function call
diff --git a/src/_pytest/assertion/util.py b/src/_pytest/assertion/util.py
index 67f8d46185e..ad7bd2c82ff 100644
--- a/src/_pytest/assertion/util.py
+++ b/src/_pytest/assertion/util.py
@@ -438,6 +438,50 @@ def _compare_eq_cls(
     return explanation
 
 
+def _call_regex(callable, pattern, string, flags, result):
+    import re, regex
+
+    def mark_errors(errors):
+        markers = [' '] * (max(errors) + 1)
+        for i in errors:
+            markers[i] = '^'
+        return ''.join(markers)
+
+    fuzzy_matchers = {
+            re.match: regex.match,
+            re.search: regex.search,
+            re.fullmatch: regex.fullmatch,
+    }
+    fuzzy_matcher = fuzzy_matchers.get(callable, callable)
+    fuzzy_pattern = '(?:%s){e}' % pattern
+    fuzzy_match = fuzzy_matcher(
+            fuzzy_pattern, 
+            string,
+            flags | regex.ENHANCEMATCH,
+    )
+    errors = fuzzy_match.fuzzy_changes
+    error_names = (
+            f'insertions:   ',
+            f'deletions:    ',
+            f'substitutions:',
+    )
+
+    n = 8
+    trunc = lambda x: f"'{x[:n-1]}…'" if len(x) > n else repr(x)
+    lines = [
+            f'{callable.__module__}.{callable.__qualname__}({trunc(pattern)}, {trunc(string)}, flags={flags})'
+            f'',
+            f'',
+            f'pattern:       {pattern}',
+            f'string:        {string}',
+    ]
+    for error, name in zip(errors, error_names):
+        if error:
+            lines += [f'{name} {mark_errors(error)}']
+
+    return '\n'.join(lines)
+
+
 def _notin_text(term: str, text: str, verbose: int = 0) -> List[str]:
     index = text.find(term)
     head = text[:index]