Cuffing Season Advice: How to Filter Your Dating Options

Cuffing Season is here, and if you’re like me, you’re ready to date with purpose. Preseason is the time to vet your prospects seriously, like a team choosing its MVP. If you don’t know what you’re truly looking for in a partner, you’ll accept anything that feels or looks good on the surface. But if you’re intentional, you’ll date with clear expectations, creating meaningful connections that last beyond the colder months.

“If you can’t identify the things that you want out of a partnership, you’ll accept anything. Anything that feels good, anything that looks good, but when you go with the intentions of knowing what you truly want, you won’t go through dating blindly.”

—Chrissy A.

Ready to dig deeper? Order our Icebreakers Cards for intentional dating questions that reveal more than surface-level traits.

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When you’re gearing up for Cuffing Season, knowing your desires and boundaries is essential. Many people dismiss the idea of a “dating checklist,” but I believe there’s a healthy side to it. My own checklist includes things like wanting a partner who loves my children, values travel, and shares my faith.

“My checklist included: I want to travel with my partner, I want someone who loves my children, who loves God, who prays with me.”

—Chrissy A.

This checklist isn’t about superficial demands; it’s about clarity. It helps you and potential partners see if your values align, which is the foundation of intentional dating. By knowing what you genuinely desire, you avoid dating just for the sake of dating and instead focus on finding someone who complements your life in meaningful ways.

Intentional dating isn’t just about attraction; it’s about creating emotional intimacy. During our podcast, Sir Anthony asked me, “What other forms of intimacy do you enjoy that don’t involve sex?” This question goes beyond physical attraction, inviting us to explore the many ways we can connect, like through open communication, shared experiences, or even just enjoying each other’s company.

Non-physical intimacy allows couples to bond in unique ways, helping us appreciate the person beneath the surface. That’s what makes intentional dating so powerful—it encourages vulnerability and openness.

Vulnerability often gets a bad reputation, especially among men, but in reality, it’s vital for a healthy, committed relationship. In our conversation, I asked Sir Anthony, “Everyone needs healing, what is one thing from your past you feel is hard to let go?” By sharing his struggles with anger management and understanding how his upbringing influenced his behavior, we created a space of empathy and support.

Intentional dating fosters these kinds of moments, allowing partners to open up and be seen for who they truly are. Vulnerability isn’t a weakness; it’s a strength that builds trust and understanding.

When you date with purpose, honest conversations are non-negotiable, and that’s where our Icebreakers Cards come in. They’re designed to bring out the questions that reveal the real person beneath the surface. From emotional healing to future goals, these cards go beyond typical small talk, helping you and your partner discover if you’re truly compatible.

Intentional dating isn’t about “cuffing” someone for the season—it’s about finding someone who fits into your life in a meaningful way. This preseason of Cuffing Season, think about what you genuinely want, embrace vulnerability, and don’t be afraid to set standards that align with your values. Whether you’re new to dating or looking to deepen an existing relationship, dating with purpose brings you closer to real, lasting love.

The Icebreakers Cards guide you through meaningful questions that deepen understanding and uncover genuine compatibility.
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