Lily Womble has got main character energy, and she’s on a mission to bring it out in everyone else, too, particularly in our dating lives. “Dating is a microcosm of wellbeing,” she believes. When she held a workshop on the subject at the LINE DC, we had her sit down for a roundtable discussion with our podcast host Jack Inslee (in a relationship), Maya Oren, brand manager (in a relationship), and Dante Cunningham, head of security (recently single and trying to date again).

Lily Womble was a matchmaker in New York who’d set up 499 dates. But only a small percentage of her clients were finding love, and she herself was trapped in a toxic relationship. Once out, she asked herself, “How do I never settle again?” and found answers in the work of discovering what lay beneath her patterns. With what she learned, she changed her whole approach and founded @datebrazen to teach others what she’d learned. In this episode, Lily reminds us what dating apps are actually designed to do, gives detailed strategies on how to navigate those apps, and even assigns Dante — and hetero men everywhere — some homework.

Hold The Booze: The Rise of Non Alcoholic Drinks

Hear HEREBy The LINE HotelSep 13, 2023