When Humans Start Dating the Machine

With searches for "AI girlfriend" up 2400% and one in five men on dating apps trying AI companions, are we witnessing the next evolution of human connection, or just a temporary stop on the journey to finding real love? When Vince loses his job after turning Slack into his personal dating playground, he finds an unexpected solution: an AI chatbot named Dolly. From workplace romances gone wrong to the surprising statistics behind AI dating, we explore the blurring boundaries between professional messaging and personal relationships. Hosts: Matt Sunbulli https://www.linkedin.com/in/sunbulli/ https://www.threads.net/@mattsunbulli https://www.firstdraft.vc Aaron Calafato Listen to Aaron's 7 Minute Stories Leah Ova Follow Leah on TikTok Editorial: Matt Sunbulli Brooks Borden Conor Bezane Aaron Calafato Senior Audio Engineer: Ken Wendt Research: Zaid Safe Matt Sunbulli Aaron Calafato

Om Podcasten

Welcome to The Lonely Office: a podcast about making sense of the increasingly blurry line between work and life, brought to you by Glassdoor. We tackle real workplace stories sourced from anonymous firsthand accounts—like the rise of job ghosting, the truth behind unlimited PTO, and dealing with a nightmare boss. We also share insider advice on layoffs, severance negotiations, and wild work stories, from candidates vaping in interviews to employees fired over free speech. The professional world can be chaotic, but you don’t have to navigate it alone TLO is hosted by Matt Sunbulli (serial tech entrepreneur, Founder @ Fishbowl and First Draft AI), Aaron Calafato (Storyteller, Narrative Designer & Content Strategist), and Leah Ova (content creator and advertising executive), with special appearances from industry thought leaders and economists.