diff --git a/spec/std/string_spec.cr b/spec/std/string_spec.cr
index ddf4bdabd67d..409413a5635b 100644
--- a/spec/std/string_spec.cr
+++ b/spec/std/string_spec.cr
@@ -925,6 +925,8 @@ describe "String" do
     it { "foobar".starts_with?("").should be_true }
     it { "foobar".starts_with?("foobarbaz").should be_false }
     it { "foobar".starts_with?("foox").should be_false }
+    it { "foobar".starts_with?(/foo/).should be_true }
+    it { "foobar".starts_with?(/bar/).should be_false }
     it { "foobar".starts_with?('f').should be_true }
     it { "foobar".starts_with?('g').should be_false }
     it { "よし".starts_with?('よ').should be_true }
@@ -936,6 +938,8 @@ describe "String" do
     it { "foobar".ends_with?("").should be_true }
     it { "foobar".ends_with?("foobarbaz").should be_false }
     it { "foobar".ends_with?("xbar").should be_false }
+    it { "foobar".ends_with?(/bar/).should be_true }
+    it { "foobar".ends_with?(/foo|baz/).should be_false }
     it { "foobar".ends_with?('r').should be_true }
     it { "foobar".ends_with?('x').should be_false }
     it { "よし".ends_with?('し').should be_true }
diff --git a/src/string.cr b/src/string.cr
index 14f9ecf4f68d..ad95f6957a37 100644
--- a/src/string.cr
+++ b/src/string.cr
@@ -3969,6 +3969,10 @@ class String
     false
   end
 
+  def starts_with?(re : Regex)
+    !!($~ = re.match_at_byte_index(self, 0, Regex::Options::ANCHORED))
+  end
+
   def ends_with?(str : String)
     return false if str.bytesize > bytesize
     (to_unsafe + bytesize - str.bytesize).memcmp(str.to_unsafe, str.bytesize) == 0
@@ -3991,6 +3995,10 @@ class String
     true
   end
 
+  def ends_with?(re : Regex)
+    !!($~ = /#{re}\z/.match(self))
+  end
+
   # Interpolates *other* into the string using `Kernel#sprintf`.
   #
   # ```