The main goal of this thesis is to show the advantage of further discussion on nostalgia in relation to retellings of fairy tales. I claim that employing Svetlana Boym’s distinction between reflective and restorative nostalgia as framework will result in a more complex and nuanced discussion on what makes retellings of fairy tale more or less progressive. By looking at retellings of Charles Perrault’s “Bluebeard” by Donald Barthelme, Angela Carter, Joyce Carol Oates, Helen Oyeyemi, and John Updike, I will look at how they utilise nostalgia to explore gender issues. It is my assessment that retellings which lean towards a more reflective nostalgia manage to better examine gender issues in a progressive way. The retellings leaning towards restorative nostalgia tend to get stuck in the past, trying to restore a romanticised image/event/time. I will explore how retellings which utilise reflective rather than restorative nostalgia examine issues such as sexual politics and the normalisation of patriarchal discourse in a way that resonates for readers today. They use the nostalgia to create a dialogue between the past and present, emphasising history’s tendency to repeat itself. Through this dialectic, they emphasise the unnatural construction of gender and reveal a naturalisation of violence towards women.