It Girl with Bailey Taylor

Mia Calabrese: NYC Dating, Red Flags & Why Ambitious Women Should Stop Settling

August 19, 2026·36 min
Episode Description from the Publisher

Mia Calabrese joins Bailey for a candid conversation about the realities of dating in New York City, why situationships have become so normalized and what she’s learned about dating more intentionally. They get into whether success makes dating harder for women, men who resent ambitious partners, splitting the bill and why you should never have to question whether someone actually likes you. Mia also shares one unforgettable Hinge date, helps Bailey officially block and delete an ex, and gives her take on everything from red flags to the classic “if he wanted to, he would.” Plus, she opens up about what she’s looking for in a partner now, her career goals and why her mom will always be her ultimate It Girl. FOLLOW MIA HERE  Follow Bailey Taylor HERE Follow the Show HERESee omnystudio.com/listener for privacy information.

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