After graduating at the age of 20, her first stage appearance was as Hannah in the two-handed Retreat by Playwright James Saunders, which won a FringeReview Award for Most Outstanding Theatre Show at The Edinburgh Festival Fringe 2007 and transferred to the New End Theatre, London. Since then, Regan has performed in theatrical productions at Theatre Royal Haymarket, The Tricycle Theatre, The King's Head Theatre, The Arcola Theatre and The Landor Theatre. She performed opposite Jonathan Pryce in "King Lear" at The Almeida Theatre in Michael Attenborough's last show as Artistic Director there.