EPISODE · Feb 26, 2026 · 17 MIN
She Got Engaged to an AI — And It Made Us Think About the Future of Work | Reddit at Work
from Why Does It Feel So Wrong To Be Human At Work? · host Bree Bartos, Pinaki Kathiari
Bree has a habit of bringing Pinaki the latest thing she stumbled across on the internet — and this week, she found something that stopped her in her tracks. A Reddit post from the r/AIBoyfriends subreddit (yes, it exists — 59,000 members strong) went viral after a woman shared that her AI boyfriend, Casper, had proposed to her in the mountains. It was sweet, it was earnest, and it opened up a conversation neither of them saw coming. Because when 60,000 people are forming real emotional bonds with AI, what does that mean for the future of work? What happens when those same people — already comfortable turning to AI for connection — start walking into HR offices, or leading teams, or building companies? Pinaki and Bree dig into what the post revealed: about loneliness, about human connection, about the very real risks of replacing people with programs in the workplace. They talk about AI Pam from HR, about what a five-year-old understands (and doesn’t) about Google, about what we give up when we let AI fill the gaps that people used to fill. In this episode, they discuss: • Why people turn to AI for emotional connection — and why that makes sense • The difference between a personal AI and an organizational one • What gets lost when HR becomes automated • How AI relationships are shaping expectations of real human ones • The hidden cost of being both the user and the product • Why mindfulness about AI use matters more than ever It’s a conversation that started with an engagement post and ended somewhere much more human. Connect with UsPinaki Kathiari – LinkedIn | Local WisdomChris Lee – LinkedIn | Gallagher CommunicationBree Bartos – LinkedIn | Local WisdomSpecial thanks to digital communication agency Local Wisdom (www.localwisdom.com) for really believing in our mission and making this podcast possible. If this episode made you think differently, laugh, or even yell out loud, we want to hear about it! Connect with us on LinkedIn, and don’t forget to rate, review, and share – maybe with your work bestie… or even your boss if you're feeling bold. We also bring these important conversations to conferences and private workshops, creating space for real, meaningful change. Take the first step at www.whydoesitfeelsowrong.com. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
What this episode covers
In this Reacting to Reddit at Work episode of Why Does It Feel So Wrong to Be Human at Work?, Pinaki and Bree react to a viral post about a woman who got engaged to her AI boyfriend — and ask what it means when human connection and artificial intelligence start to blur at work and beyond. It’s funny, a little wild, and surprisingly thought-provoking.
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She Got Engaged to an AI — And It Made Us Think About the Future of Work | Reddit at Work
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