diff --git a/spec/matchers/contain_matcher_spec.cr b/spec/matchers/contain_matcher_spec.cr
index 3f7bd5e..87efc4d 100644
--- a/spec/matchers/contain_matcher_spec.cr
+++ b/spec/matchers/contain_matcher_spec.cr
@@ -3,125 +3,263 @@ require "../spec_helper"
 describe Spectator::Matchers::ContainMatcher do
   describe "#match?" do
     context "with a String" do
-      context "against a matching string" do
-        it "is true" do
-          value = "foobarbaz"
-          search = "bar"
-          partial = Spectator::Expectations::ValueExpectationPartial.new(value)
-          matcher = Spectator::Matchers::ContainMatcher.new({search})
-          matcher.match?(partial).should be_true
-        end
-
-        context "at the beginning" do
+      context "one argument" do
+        context "against a matching string" do
           it "is true" do
-            value = "foobar"
-            search = "foo"
-            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
-            matcher = Spectator::Matchers::ContainMatcher.new({search})
-            matcher.match?(partial).should be_true
-          end
-        end
-
-        context "at the end" do
-          it "is true" do
-            value = "foobar"
+            value = "foobarbaz"
             search = "bar"
             partial = Spectator::Expectations::ValueExpectationPartial.new(value)
             matcher = Spectator::Matchers::ContainMatcher.new({search})
             matcher.match?(partial).should be_true
           end
-        end
-      end
 
-      context "against a different string" do
-        it "is false" do
-          value = "foobar"
-          search = "baz"
-          partial = Spectator::Expectations::ValueExpectationPartial.new(value)
-          matcher = Spectator::Matchers::ContainMatcher.new({search})
-          matcher.match?(partial).should be_false
-        end
-      end
+          context "at the beginning" do
+            it "is true" do
+              value = "foobar"
+              search = "foo"
+              partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+              matcher = Spectator::Matchers::ContainMatcher.new({search})
+              matcher.match?(partial).should be_true
+            end
+          end
 
-      context "against a matching character" do
-        it "is true" do
-          value = "foobar"
-          search = 'o'
-          partial = Spectator::Expectations::ValueExpectationPartial.new(value)
-          matcher = Spectator::Matchers::ContainMatcher.new({search})
-          matcher.match?(partial).should be_true
+          context "at the end" do
+            it "is true" do
+              value = "foobar"
+              search = "bar"
+              partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+              matcher = Spectator::Matchers::ContainMatcher.new({search})
+              matcher.match?(partial).should be_true
+            end
+          end
         end
 
-        context "at the beginning" do
+        context "against a different string" do
+          it "is false" do
+            value = "foobar"
+            search = "baz"
+            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+            matcher = Spectator::Matchers::ContainMatcher.new({search})
+            matcher.match?(partial).should be_false
+          end
+        end
+
+        context "against a matching character" do
           it "is true" do
             value = "foobar"
-            search = 'f'
+            search = 'o'
             partial = Spectator::Expectations::ValueExpectationPartial.new(value)
             matcher = Spectator::Matchers::ContainMatcher.new({search})
             matcher.match?(partial).should be_true
           end
+
+          context "at the beginning" do
+            it "is true" do
+              value = "foobar"
+              search = 'f'
+              partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+              matcher = Spectator::Matchers::ContainMatcher.new({search})
+              matcher.match?(partial).should be_true
+            end
+          end
+
+          context "at the end" do
+            it "is true" do
+              value = "foobar"
+              search = 'r'
+              partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+              matcher = Spectator::Matchers::ContainMatcher.new({search})
+              matcher.match?(partial).should be_true
+            end
+          end
         end
 
-        context "at the end" do
-          it "is true" do
+        context "against a different character" do
+          it "is false" do
             value = "foobar"
-            search = 'r'
+            search = 'z'
             partial = Spectator::Expectations::ValueExpectationPartial.new(value)
             matcher = Spectator::Matchers::ContainMatcher.new({search})
-            matcher.match?(partial).should be_true
+            matcher.match?(partial).should be_false
           end
         end
       end
 
-      context "against a different character" do
-        it "is false" do
-          value = "foobar"
-          search = 'z'
-          partial = Spectator::Expectations::ValueExpectationPartial.new(value)
-          matcher = Spectator::Matchers::ContainMatcher.new({search})
-          matcher.match?(partial).should be_false
+      context "multiple arguments" do
+        context "against matching strings" do
+          it "is true" do
+            value = "foobarbaz"
+            search = {"foo", "bar", "baz"}
+            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+            matcher = Spectator::Matchers::ContainMatcher.new(search)
+            matcher.match?(partial).should be_true
+          end
+        end
+
+        context "against one matching string" do
+          it "is false" do
+            value = "foobarbaz"
+            search = {"foo", "qux"}
+            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+            matcher = Spectator::Matchers::ContainMatcher.new(search)
+            matcher.match?(partial).should be_false
+          end
+        end
+
+        context "against no matching strings" do
+          it "is false" do
+            value = "foobar"
+            search = {"baz", "qux"}
+            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+            matcher = Spectator::Matchers::ContainMatcher.new(search)
+            matcher.match?(partial).should be_false
+          end
+        end
+
+        context "against matching characters" do
+          it "is true" do
+            value = "foobarbaz"
+            search = {'f', 'b', 'z'}
+            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+            matcher = Spectator::Matchers::ContainMatcher.new(search)
+            matcher.match?(partial).should be_true
+          end
+        end
+
+        context "against one matching character" do
+          it "is false" do
+            value = "foobarbaz"
+            search = {'f', 'c', 'd'}
+            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+            matcher = Spectator::Matchers::ContainMatcher.new(search)
+            matcher.match?(partial).should be_false
+          end
+        end
+
+        context "against no matching characters" do
+          it "is false" do
+            value = "foobarbaz"
+            search = {'c', 'd', 'e'}
+            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+            matcher = Spectator::Matchers::ContainMatcher.new(search)
+            matcher.match?(partial).should be_false
+          end
+        end
+
+        context "against a matching string and character" do
+          it "is true" do
+            value = "foobarbaz"
+            search = {"foo", 'z'}
+            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+            matcher = Spectator::Matchers::ContainMatcher.new(search)
+            matcher.match?(partial).should be_true
+          end
+        end
+
+        context "against a matching string and non-matching character" do
+          it "is false" do
+            value = "foobarbaz"
+            search = {"foo", 'c'}
+            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+            matcher = Spectator::Matchers::ContainMatcher.new(search)
+            matcher.match?(partial).should be_false
+          end
+        end
+
+        context "against a non-matching string and matching character" do
+          it "is false" do
+            value = "foobarbaz"
+            search = {"qux", 'f'}
+            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+            matcher = Spectator::Matchers::ContainMatcher.new(search)
+            matcher.match?(partial).should be_false
+          end
+        end
+
+        context "against a non-matching string and character" do
+          it "is false" do
+            value = "foobarbaz"
+            search = {"qux", 'c'}
+            partial = Spectator::Expectations::ValueExpectationPartial.new(value)
+            matcher = Spectator::Matchers::ContainMatcher.new(search)
+            matcher.match?(partial).should be_false
+          end
         end
       end
     end
 
     context "with an Enumberable" do
-      context "against an equal value" do
-        it "is true" do
-          array = %i[a b c]
-          search = :b
-          partial = Spectator::Expectations::ValueExpectationPartial.new(array)
-          matcher = Spectator::Matchers::ContainMatcher.new({search})
-          matcher.match?(partial).should be_true
-        end
-
-        context "at the beginning" do
+      context "one argument" do
+        context "against an equal value" do
           it "is true" do
             array = %i[a b c]
-            search = :a
+            search = :b
             partial = Spectator::Expectations::ValueExpectationPartial.new(array)
             matcher = Spectator::Matchers::ContainMatcher.new({search})
             matcher.match?(partial).should be_true
           end
+
+          context "at the beginning" do
+            it "is true" do
+              array = %i[a b c]
+              search = :a
+              partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+              matcher = Spectator::Matchers::ContainMatcher.new({search})
+              matcher.match?(partial).should be_true
+            end
+          end
+
+          context "at the end" do
+            it "is true" do
+              array = %i[a b c]
+              search = :c
+              partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+              matcher = Spectator::Matchers::ContainMatcher.new({search})
+              matcher.match?(partial).should be_true
+            end
+          end
         end
 
-        context "at the end" do
-          it "is true" do
+        context "against a different value" do
+          it "is false" do
             array = %i[a b c]
-            search = :c
+            search = :z
             partial = Spectator::Expectations::ValueExpectationPartial.new(array)
             matcher = Spectator::Matchers::ContainMatcher.new({search})
-            matcher.match?(partial).should be_true
+            matcher.match?(partial).should be_false
           end
         end
       end
 
-      context "against a different value" do
-        it "is false" do
-          array = %i[a b c]
-          search = :z
-          partial = Spectator::Expectations::ValueExpectationPartial.new(array)
-          matcher = Spectator::Matchers::ContainMatcher.new({search})
-          matcher.match?(partial).should be_false
+      context "multiple arguments" do
+        context "against equal values" do
+          it "is true" do
+            array = %i[a b c]
+            search = {:a, :b}
+            partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+            matcher = Spectator::Matchers::ContainMatcher.new(search)
+            matcher.match?(partial).should be_true
+          end
+        end
+
+        context "against one equal value" do
+          it "is false" do
+            array = %i[a b c]
+            search = {:a, :d}
+            partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+            matcher = Spectator::Matchers::ContainMatcher.new(search)
+            matcher.match?(partial).should be_false
+          end
+        end
+
+        context "against no equal values" do
+          it "is false" do
+            array = %i[a b c]
+            search = {:d, :e}
+            partial = Spectator::Expectations::ValueExpectationPartial.new(array)
+            matcher = Spectator::Matchers::ContainMatcher.new(search)
+            matcher.match?(partial).should be_false
+          end
         end
       end
     end