diff --git a/app/views/dashboard/todos/index.html.haml b/app/views/dashboard/todos/index.html.haml
index 5b2465e25ee..472d698486b 100644
--- a/app/views/dashboard/todos/index.html.haml
+++ b/app/views/dashboard/todos/index.html.haml
@@ -84,7 +84,7 @@
       = render "shared/empty_states/todos_all_done.svg"
       - if todos_filter_empty?
         %h4.text-center
-          Good job! Looks like you don't have any todos left.
+          = Gitlab.config.gitlab.no_todos_messages.sample
         %p.text-center
           Are you looking for things to do? Take a look at
           = succeed "," do
diff --git a/changelogs/unreleased/issue-13823.yml b/changelogs/unreleased/issue-13823.yml
new file mode 100644
index 00000000000..c1b5760f7df
--- /dev/null
+++ b/changelogs/unreleased/issue-13823.yml
@@ -0,0 +1,4 @@
+---
+title: Show random messages when the To Do list is empty
+merge_request: 6818
+author: Josep Llaneras
diff --git a/config/initializers/1_settings.rb b/config/initializers/1_settings.rb
index 9fec2ad6bf7..9ddd1554811 100644
--- a/config/initializers/1_settings.rb
+++ b/config/initializers/1_settings.rb
@@ -215,6 +215,7 @@ Settings.gitlab.default_projects_features['visibility_level']   = Settings.send(
 Settings.gitlab['domain_whitelist'] ||= []
 Settings.gitlab['import_sources'] ||= %w[github bitbucket gitlab google_code fogbugz git gitlab_project]
 Settings.gitlab['trusted_proxies'] ||= []
+Settings.gitlab['no_todos_messages'] ||= YAML.load_file(Rails.root.join('config', 'no_todos_messages.yml'))
 
 #
 # CI
diff --git a/config/no_todos_messages.yml b/config/no_todos_messages.yml
new file mode 100644
index 00000000000..8372fb4ebe9
--- /dev/null
+++ b/config/no_todos_messages.yml
@@ -0,0 +1,13 @@
+# When the Todos list on the user's dashboard becomes empty, one of the messages below shows up randomly.
+#
+# If you come up with a fun one, please feel free to contribute it to GitLab!
+# https://about.gitlab.com/contributing/
+
+--- 
+- Good job! Looks like you don't have any todos left.
+- Coffee really tastes better without any todos left.
+- Isn't an empty To Do list beautiful?
+- Time for a rewarding coffee break
+- Give yourself a pat on the back!
+- High five!
+- Hence forth you shall be known as 'Todo Destroyer'
\ No newline at end of file
diff --git a/spec/features/todos/todos_spec.rb b/spec/features/todos/todos_spec.rb
index 3ae83ac082d..88eabea7e3a 100644
--- a/spec/features/todos/todos_spec.rb
+++ b/spec/features/todos/todos_spec.rb
@@ -44,7 +44,7 @@ describe 'Dashboard Todos', feature: true do
         end
 
         it 'shows "All done" message' do
-          expect(page).to have_content("Good job! Looks like you don't have any todos left.")
+          expect(page).to have_selector('.todos-all-done', count: 1)
         end
       end
 
@@ -64,7 +64,7 @@ describe 'Dashboard Todos', feature: true do
           end
 
           it 'shows "All done" message' do
-            expect(page).to have_content("Good job! Looks like you don't have any todos left.")
+            expect(page).to have_selector('.todos-all-done', count: 1)
           end
         end
       end
@@ -152,7 +152,7 @@ describe 'Dashboard Todos', feature: true do
         within('.todos-pending-count') { expect(page).to have_content '0' }
         expect(page).to have_content 'To do 0'
         expect(page).to have_content 'Done 0'
-        expect(page).to have_content "Good job! Looks like you don't have any todos left."
+        expect(page).to have_selector('.todos-all-done', count: 1)
       end
     end
   end