Sean Patrick Thomas portrayed Ronald in Segundas Intenções (1999). He also originally had scenes in Segundas Intenções 2 (2000) that ended up on the cutting room floor.
This will mark the third attempt at a television series based on the world of Segundas Intenções (1999). The straight-to-video sequel Segundas Intenções 2 (2000), with Amy Adams replacing Sarah Michelle Gellar as Kathryn Merteuil, was originally a scripted TV series before being re-edited into a feature film. Gellar would later reprise her role as Kathryn in 2016 for the NBC pilot Cruel Intentions (2016), which was not ordered to series.
Officially cancelled after one season on March 10, 2025. Nearly 4 months after its release with little to no promo from Prime Video after it premiered.
Filmed in Toronto, Ontario, Canada.
Jenna Ortega was considered for the role of Caroline Merteuil, and Shawn Mendes was the first choice to play Lucien Belmont. JoJo Siwa was considered for CeCe but the producers decided to go with an unknown and cast Sara Silva.