diff --git a/app/controllers/markdown_controller.rb b/app/controllers/markdown_controller.rb
index 60768a170..a4c59cdd9 100644
--- a/app/controllers/markdown_controller.rb
+++ b/app/controllers/markdown_controller.rb
@@ -3,7 +3,7 @@ class MarkdownController < ApplicationController
   respond_to :js
 
   def preview
-    markdown_source = params[:source].to_str.gsub(/:([\w+-]+):/) do |match|
+    markdown_source = params[:source].to_str.gsub(/ :([\w+-]+): /) do |match|
                         %(![add-emoji](https://github.githubassets.com/images/icons/emoji/#{match.to_str.tr(':','')}.png))
                       end if params[:source]
     @rendered = MarkdownHelper.render markdown_source
diff --git a/app/helpers/application_helper.rb b/app/helpers/application_helper.rb
index 97e618d5f..169e46661 100644
--- a/app/helpers/application_helper.rb
+++ b/app/helpers/application_helper.rb
@@ -23,7 +23,7 @@ def active_page_size(page_size, param=nil)
   end
 
   def emojify content
-    content.to_str.gsub(/:([\w+-]+):/) do |match|
+    content.to_str.gsub(/ :([\w+-]+): /) do |match|
       %(![add-emoji](https://github.githubassets.com/images/icons/emoji/#{match.to_str.tr(':','')}.png))
     end.html_safe if content.present?
   end