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.

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Timestamps:

0:00 - Welcome Dini To The Show!

1:00 - Dating Today - paradox of choice

4:00 - We had OkCupid, then Hinge, and now ????

7:00 - B2B AI SaaS your love life?

12:00 - Compatibility & Connection

18:30 - The gender wars

22:00 - 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 bathrooms

40:00 - What we all misunderstand about love and what’s really important

46:00 - The keys to good conflict resolution

50:00 - Thanks For Watching! Like & Subscribe