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Dating coach Tony Tedesco flips the usual red flag conversation on its head, explaining why the way someone describes a past relationship tells you almost everything you need to know. Anyone tired of scanning profile pictures for clues will want a better filter, and this is one worth stealing.

Jen Kirsch adds her own list, from valuing therapy and self-awareness to why keeping small promises matters more than grand gestures, plus the exact kind of apology that actually rebuilds trust.

The two trade takes on spontaneity, comfortable silence, and why a friendship's value has less to do with how many years it has lasted and more to do with whether it is still active today.

Topics: dating green flags, emotional maturity, relationship reliability, apologizing well, comfortable silence

GUEST: Jen Kirsch | @‌jen_kirsch
GUEST: Tony Tedesco | @‌tedescotony

Originally aired on 2026-07-28