From Loss to Love: Reinventing Dating with Clarity, Confidence & Connection

Apr 9, 2025

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Introduction

In this episode of Life Check Yourself, we sit down with the incredible Jen Crowley, a woman who has walked through love, loss, and the courageous journey of rediscovering herself. After losing her husband, Tyke, to cancer in 2015, Jen faced the overwhelming challenge of navigating dating again. With determination and a willingness to embrace new possibilities, she ultimately found love once more and is now engaged to Jeff.

Jen’s story is a powerful testament to the fact that love exists when we are willing to heal, redefine what we truly need, and take intentional steps toward the right relationship. Today, we’re diving deep into the mindset shifts, dating strategies, and personal breakthroughs that helped Jen find her way back to love.

3 Powerful Takeaways

Clarity is everything—knowing what you want changes the game.
Online dating isn’t about luck; it’s about strategy and alignment.
The right relationship feels supportive, safe, and deeply fulfilling.

Key Topics & Timestamps

Defining Your Non-Negotiables & Dating with Clarity (12:05)

“You have to know what you’re looking for—otherwise, you’ll keep settling.”

"The right relationship isn’t just about chemistry. It’s about shared values, mutual respect, and a future vision that aligns."

Without a clear understanding of what truly matters, dating can feel like an endless cycle of trial and error. Defining non-negotiables isn’t about being picky—it’s about saving time and energy by only investing in people who align with what you genuinely need in a relationship. When you’re crystal clear on what matters, making dating decisions becomes easier and more intentional.

Overcoming the Fear of Online Dating & Taking Strategic Action (23:40)

"I was afraid of being lied to, but I also knew there had to be a way to navigate this better."

"Instead of dreading the process, I learned how to filter out the noise and focus on real connections."

Fear often holds people back from fully embracing online dating. Worries about deception, wasted time, and rejection can create resistance to putting yourself out there. But instead of staying stuck, learning how to strategically approach dating—through filtering, discernment, and proactive engagement—makes all the difference. Taking control of the process means dating smarter, not harder.

Building a Relationship That Feels Safe & Empowering (35:15)

"The best relationships feel like a partnership, where both people give 80% rather than keeping score."

"Communication should feel safe and open, where you can say what you need without fear of judgment."

A truly fulfilling relationship is built on mutual support, generosity, and the ability to communicate honestly. When both partners are committed to creating a space of trust and appreciation, love naturally deepens. Rather than settling for surface-level connections, choosing someone who makes you feel valued and understood creates a foundation for lasting happiness.

Final Thoughts

Jen’s journey reminds us that love isn’t about waiting—it’s about taking action. When we heal, define our values, and approach dating with confidence, the right relationship can unfold in ways we never imagined.

If you’ve been feeling stuck in love, this conversation is your sign to reset, get clear, and take the next step with intention.

Listen to the full episode now and start creating the love story you truly deserve!

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