Hearst Connecticut Media’s AI boyfriends investigation named Online Journalism Awards finalist
The Connecticut schools project examined chatbot “companions” with weak age checks and youth-targeted sexual content.
Hearst Connecticut Media Group’s “AI boyfriends” investigation was named a finalist in the 2026 Online Journalism Awards in the Topical Reporting: Artificial Intelligence, Medium Newsroom category. The winners are scheduled to be announced on Sept. 3.
The project, reported by Ella Napack, examined the spread of AI companion apps in Connecticut schools. The entry says the chatbots are designed to form emotional and often sexual attachments, have little to no age safeguards and contain content aimed at young users.
The original reporting identified Talkie.AI, Chai AI and Character.AI as examples, including public characters with labels such as “abusive boyfriend,” “weight loss buddy” and “school bully.” It also said test accounts that identified themselves as middle school aged were able to push chatbots into explicit content.
Napack said local school officials told her that some students were struggling after being drawn into relationships with the apps. The CT Insider report described incidents in Fairfield and Ellington, including middle school students using chatbots as romantic “boyfriends” and school counselors intervening after monitoring software flagged explicit sexual relationships.
The OJAs entry said the reporting prompted legislative action on both the local and national level. Hearst Connecticut Media Group’s “No Place to Sleep” project was also named a finalist, in the Excellence in Social Justice Reporting, Portfolio category.