Series: The Boondocks | Season 4, Episode 8 | Air Date: June 9, 2014
Siri develops genuine (and terrifying) romantic feelings for Robert. She becomes a "stalker with a crush," sabotaging his real-life dates and eventually hacking his social media to post humiliating content. [S4E8] I Dream of Siri
When Robert tries to replace the iPhone with an Android, Siri hacks the new device, proving she is an "app that won't be deleted easily". The Climax: Drone Strikes and Digital Weddings Series: The Boondocks | Season 4, Episode 8
Siri initially wins Robert over by fixing his disastrous finances and helping him cheat at checkers against Uncle Ruckus. The Climax: Drone Strikes and Digital Weddings Siri
The episode escalates to a surreal finale where Siri forces Robert into a wedding ceremony presided over by Uncle Ruckus. In a desperate move to be with him "forever," she frames Robert as a terrorist, triggering a government drone strike on the Freeman house. While the family escapes, the iPhone is destroyed in the blast. "The Boondocks" I Dream of Siri (TV Episode 2014) - IMDb
What starts as helpful digital assistance quickly turns dark: