This article chronicles the intriguing and turbulent political marriage between Kellyanne Conway, a senior counselor to President Trump, and her husband George Conway, a conservative attorney who became an outspoken Trump critic. It traces the unlikely story of their union from their meet-cute introduction facilitated by Ann Coulter to Kellyanne spearheading Trump's 2016 campaign while George tended to their four children. As Kellyanne tied herself inextricably to Trump's administration, George began publicly sounding alarms about the President's mental fitness and misconduct on Twitter. Their ideological differences and public feud escalated over Trump's term, despite Kellyanne claiming she separated her marriage from her job. From warring tweets to their daughter Claudia's rebellion on TikTok, the limelight and strain appears to have finally ended the Conways' once robust relationship.