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<?php $message = 'choukai kai hey this matches too 432-2123'; $search = array('surfing', 'joke and stuff', 'smile and etc', '3-2', 'choukai kai', 'choukai'); // Massage the message $message = preg_replace( '/(' . implode('|', array_map('preg_quote', $search)) . ')/i', '%%$1%%', $message ); var_dump($message); $replacements = array( // here all replaces | each in a new line - watch the syntax // all html possible, but no single quotation mark! '<a href="http://en.wikipedia.org/wiki/Surfing" style="color:darkred;font-weight:bold;">surfing</a>', '<a href="http://en.wikipedia.org/wiki/Joke" style="color:darkred;font-weight:bold;">joke</a>', '<a href="http://en.wikipedia.org/wiki/Smiling" style="color:darkred;font-weight:bold;">Smile</a>', '<a class="screenshot" rel="3-2_Map.jpg">3-2</a>', '<a href="http://en.wikipedia.org/wiki/Joke" style="color:darkred;font-weight:bold;">Choukai Kai</a>', '<a href="http://en.wikipedia.org/wiki/Smiling" style="color:darkred;font-weight:bold;">Choukai</a>' );

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