Friend played three minor roles in a stage production of The Laramie Project when he was in his third year in drama school, and was spotted by a casting director. He made his acting debut as Billy Downs opposite Johnny Depp in the 2004 film The Libertine, for which he was named "outstanding new talent" at the 2005 Satellite Awards. He later stated that working with Depp so early in his career was a great lesson in film-acting. In 2005, Friend had his first starring role as Ludovic Meyer in the film adaption of Mrs Palfrey at the Claremont, in which he starred opposite Joan Plowright. In the same year, he portrayed George Wickham in Joe Wright's version of Pride & Prejudice.
