EPISODE · Oct 23, 2025 · 50 MIN
This AI Company Wants To Save Modern Dating | Dini from Sitch
from Failing Up · host Claire
Dating today is broken. In this episode, Dini, co-founder of AI matchmaking app Sitch, joins Failing Up to talk about how we got here — from OkCupid to Hinge to whatever comes next and why it might finally be time to reinvent dating altogether.We explore the paradox of choice, the gender wars, what healthy conflict resolution in relationships look like, and why so many people chase chemistry over compatibility. Dini explains how AI could reshape human connection by removing ego, bias, and the endless swiping culture that’s left so many people burned out and disillusioned.Follow Us On IG: https://www.instagram.com/failinguppp/?hl=enListen on Spotify: https://open.spotify.com/show/3KMsmkqvycGgoXZDjoM6Py?si=6e40e75d54374c08Listen On Apple Podcasts: https://podcasts.apple.com/us/podcast/failing-up/id1771458449Timestamps:0:00 - Welcome Dini To The Show!1:00 - Dating Today - paradox of choice4:00 - We had OkCupid, then Hinge, and now ????7:00 - B2B AI SaaS your love life?12:00 - Compatibility & Connection18:30 - The gender wars22:00 - What guys vs girls do wrong (expectations and practices)31:00 - Why is there a stigma attached to dating coaches?38:00 - Couples should always have separate bathrooms40:00 - What we all misunderstand about love and what’s really important46:00 - The keys to good conflict resolution50:00 - Thanks For Watching! Like & Subscribe
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This AI Company Wants To Save Modern Dating | Dini from Sitch
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