The series is based on the young adult novel series Dash & Lily's Book of Dares by Rachel Cohn and David Levithan, adapted for Netflix by Joe Tracz who also served as showrunner.

Netflix ordered the 8-episode adaptation in October 2019, with Shawn Levy and Josh Barry of 21 Laps Entertainment, Nick Jonas of Image 32, and Brad Silberling serving as executive producers alongside original authors Cohn and Levithan as co-executive producers.

Directors on the series included executive producer Brad Silberling, as well as Fred Savage and Pamela Romanowsky.

Netflix canceled the series after just one season on October 6, 2021, despite its strong critical reception.

Nick Jonas, who co-executive produced the series through his company Image 32, also made a cameo appearance as himself, with the Jonas Brothers performing the song "Like It's Christmas" in the show.

On Rotten Tomatoes, the series earned a 100% approval rating based on 34 reviews, with critics praising leads Midori Francis and Austin Abrams for anchoring the charming holiday rom-com.

Casting was rolled out in stages: Austin Abrams and Midori Francis were announced as the leads alongside the series order in October 2019, with additional cast members like Glenn McCuen, Michael Park, and Diego Guevara announced the following month, and further actors such as Agneeta Thacker and Ianne Fields Stewart joining in March 2020.