Behind The Boss: The Softer Side of Professional Women in Love episode artwork

EPISODE · Oct 7, 2025 · 21 MIN

Behind The Boss: The Softer Side of Professional Women in Love

from Saying Yes Again: Helping midlife singles and couples rewrite their love story.

In this episode of "Saying Yes Again," Dr. Lisa and her partner Tony discuss the unique challenges professional women face in dating and relationships. They debunk myths about financial expectations, emphasizing the importance of emotional support, authenticity, and understanding each other's need for space. The conversation highlights how career-driven women can balance independence with vulnerability, set healthy boundaries, and avoid treating relationships like business transactions. The episode concludes with advice for dating with purpose and an invitation to their upcoming speed dating event for singles over 40.     Introduction: The Softer Side of Professional Women (00:00:00) Dr. Lisa introduces the duality of professional women—strong at work, but also craving love and connection. Challenging Financial Stereotypes in Relationships (00:02:26) Discussion on financial independence, emotional support, and the misconception that men's main role is financial. The Need for Space and Decompression (00:04:22): Exploring the importance of personal space, decompression, and understanding each other's need for downtime. Professional Habits Impacting Dating (00:05:42) How career-driven habits like organization and timeliness affect dating dynamics and relationships. Balancing Professionalism and Emotional Availability (00:09:00) Challenges of being emotionally available, letting go of professional guard, and showing vulnerability in dating. Advice for Professional Women in Dating (00:10:36) Tips for dating with purpose, knowing values, and being observant in early relationship stages. Don't Overwork Love (00:11:52) Encouragement to approach love with openness, not as a project or job, and to separate work from romance. Authenticity and Vulnerability (00:13:09) The importance of being authentic, vulnerable, and leaving the CEO persona at work. Setting Boundaries and Protecting Energy (00:14:26) Advice on setting boundaries, protecting time and energy, and not dating from a place of exhaustion. Embracing Both Sides: Femininity and Strength (00:16:44) Encouragement for women to show both their strong and soft sides, and for men to offer emotional security. Upcoming Speed Dating Event Announcement (00:18:00) Details about their first speed dating event for singles over 40, including how to register and what to expect. Closing and Social Media Reminders (00:20:48) Thanking listeners, encouraging sharing, and reminders to follow and subscribe for future episodes.

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Behind The Boss: The Softer Side of Professional Women in Love

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This episode is 21 minutes long.

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This episode was published on October 7, 2025.

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In this episode of "Saying Yes Again," Dr. Lisa and her partner Tony discuss the unique challenges professional women face in dating and relationships. They debunk myths about financial expectations, emphasizing the importance of emotional support,...

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