What if technology cared more about your relationship than keeping you swiping or booking endless therapy sessions? In this episode, we sit down with Jason Jiang, co-founder of Chaima AI, to explore how a new “couple’s concierge” is designed to strengthen relationships long after the first date.
Jason shares how Chaima blends AI and human concierges to plan personalized experiences, from hidden city gems to family-friendly date nights. Drawing on his background at Uber and Bird, he explains why an operations-heavy, AI-assisted model gives couples both novelty and convenience without compromising privacy.
In this episode, you’ll discover:
Why dating apps and therapy models often misalign with users’ true needs
How Chaima uses AI for planning and execution, while humans ensure trust and personalization
The delicate balance between convenience, effort, and intimacy in relationships
Why privacy and incentives matter when building relationship tech
How AI could eventually reshape therapy, conflict resolution, and emotional support
Jason also opens up about his personal journey, from a tough breakup and career pivots at top tech companies to founding Chaima, and the advice he gives founders building tech that touches love, trust, and human connection.
If you’re curious about the future of AI in relationships, dating, and the circular economy of love, this episode offers both insight and inspiration.
