Podcasts · Jillian on Love

Stop Chasing: How to Date with Confidence

· 47 min · S3 E19

Episode Stop Chasing: How to Date with Confidence

0:00 47:23

In this special coaching episode, Jillian sits down with a 38-year-old listener who’s four dates into a new connection and stuck in her head about one big question: Is he actually interested, or just passive? Together, they unpack why slow, calm chemistry can feel confusing when you’re used to intensity, what to do when someone’s texting and effort don’t quite match your needs, and how to treat early dating as data instead of a referendum on your worth. Jillian coaches her on how to flirt, set the tone without over-pursuing, keep dating other people, and show up as the most confident version of herself—even when there’s still no kiss.

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