Why You Keep Pushing Great Men Away episode artwork

EPISODE · Aug 27, 2026 · 33 MIN

Why You Keep Pushing Great Men Away

from Secrets from a Billionaires’ Matchmaker With Gina Hendrix · host Gina Hendrix

People rarely sabotage promising relationships because of what actually happened, they sabotage them because of the story they told themselves about what happened. In this episode of Secrets They’ll Only Tell a Matchmaker, with Gina Hendrix, we’re having a reality check - is the story you’re telling yourself the truth, or one you’ve made up?Gina walks through a recent matchmaking date that went sideways because both people showed up carrying baggage and skepticism instead of just meeting who was in front of them.Dating can mean playing the long game, learning about someone and really getting to know them, rather than creating stories about people we don’t really know that well yet.In this quick fire Q&A, we hear from one woman who wants to know if seeing familiar faces resurface on dating apps after a decade is a red flag, another admits she can no longer get past a slightly feminine voice, and we hear from a woman seeking advice about a date she doesn't want to go - but it's due to happen tonight!Then we hear from a woman who found herself in an uncomfortable situation - a man she'd only just started video chatting with peppered her with explicit sexual questions, we also discuss age gaps - one caller’s been told she is too old, another worries her date is only with her because she’s young.And we discuss the dangers playing detective and over-analyzing for potential red flags.The big takeaway from this episode of Secret’s They’ll Only Tell a Matchmaker: dating isn't about eliminating uncertainty as fast as possible, it's about learning to navigate it. When anxiety shows up, don't let it become your storyteller. Stay curious, gather real information, and let people reveal themselves before you decide what their story means.CHAPTERS:(00:00) Introduction (03:15) Friend Setups and Lifestyle Fit(08:18) Red Flags Age Gaps and Boundaries(16:02) Canceling the Pushy Date(22:36) Stop Red Flag Detective Mode(28:31) Standards vs Reality on Apps(31:08) Why Dating Gets Harder

Episode metadata supplied by the publisher feed · Published Aug 27, 2026

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Why You Keep Pushing Great Men Away

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This episode was published on August 27, 2026.

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