Anna Larsen is stuck. As an aspiring artist with a lot of baggage, she scrapes by as a wedding photographer, paying the bills by capturing the happiest moments of people she loathes.
Anna’s mother Claire, a federal judge, was recently diagnosed with early on-set Alzheimer’s. Anna and her mom are polar opposites with a long history of misunderstanding each other. When Anna’s brother Brian calls to ask her to come home and help care for their mom as they prepare to sell her house, Anna apprehensively agrees.
Anna arrives home to find her mother as opinionated and strong-willed as ever. Though she may lose her words, Claire has not lost her determination to call the shots on everything, including Anna’s life.
At home, Anna is also hit with childhood memories of her father leaving and her parents’ divorce. During that painful time, young Anna’s saving grace was the appearance of a mysterious mailbox and a secret correspondence with a penpal called “Dragonfly”. While packing up the house, Anna rediscovers the Dragonfly mailbox and letters, reawakening her curiosity about who the mystery penpal might have been.
As Anna searches for Dragonfly, she reconnects with her dad Phil. She confides in him about the issues with her mom and her career struggles. Phil urges Anna to “honor her magic” and pursue her work instead of selling out.
Despite warning signs that Claire’s condition is getting worse, Anna heeds her dad’s advice and tries to focus on her own life and her work, leaving Brian to pick up the slack at home. After a disastrous night with a childhood love, tensions explode, causing Anna to re-evaluate her past and what is really standing in the way of her success.