Curious about how coaching can transform your life?

Working with a dedicated coach offers clarity, support, and accountability.

You don’t have to navigate your journey alone. Book a complimentary consultation today. Services provided by Kate Woodward Coaching & Matchmaking.

  • We reject a one-size-fits-all approach to dating and relationships. While there are common best practices, we recognize that every individual and relationship is unique. That’s why we take the time to understand your specific needs and aspirations, tailoring our approach to support you in a way that feels authentic and meaningful. Our goal is to help you navigate dating with greater intention—fostering self-compassion, confidence, and deeper connections along the way.

    Together, we’ll explore how to build confidence and feel good about yourself while gently reflecting on past experiences to uncover what truly matters to you. You’ll gain insight into what makes relationships work—and how to recognize those qualities in a partner. We’ll clarify what you’re looking for, how to identify the right match, and explore dating options beyond apps or refine your online approach. This includes crafting a dating profile that reflects who you are, selecting photos that tell your story, and messaging in a way that sparks genuine interest.

    You'll also learn how to prepare for dates so you can feel confident, present, and at ease, while developing the skills to create real, meaningful connections. Along the way, we’ll provide insight into the psychology of modern dating and how it applies to your journey. With ongoing support, we’ll guide you through the first steps of dating and help you turn new connections into lasting relationships.

    No matter where you’re starting, we’re here to help you move forward with clarity, confidence, and a deeper understanding of yourself.

  • Sessions tend to last 90 minutes and often take place over Zoom. If you are located within the Washington, D.C. metro area and would prefer in-person sessions, these may be requested in advance.

    Following each session, clients receive a detailed reflection that provides an overview of challenges discussed, offers additional resources, and, perhaps most importantly, reiterates the actionable steps and goals agreed upon during the coaching conversation. We are mindful of the investment you are making by committing to the coaching process, and will seek to be a steadfast accountability partner in order to ensure you meet your goals and spark the change you are seeking.

  • It’s okay to wonder how coaching differs from therapy — both can be incredibly valuable, but they serve different purposes.

    Coaching is about:

    • Setting clear, practical goals for your dating life and relationships

    • Identifying where you feel stuck and creating strategies to move forward

    • Practicing new skills and behaviors in a supportive, judgment-free space

    • Staying motivated, encouraged, and accountable to your goals

    • Learning about dating dynamics and how to navigate them with ease

    • Developing resilience to handle challenges along the way

    • Taking small but meaningful actions to keep growing between sessions

    Coaching is often lighter and more forward-focused than therapy. It’s about giving you tools, strategies, and encouragement to create positive change.

    Therapy focuses more on:

    • Exploring who you are and what gives your life meaning

    • Identifying and processing sources of unhappiness or emotional pain

    • Understanding how your past might be shaping your present

    • Developing coping strategies to handle deeper personal challenges

    Therapy is introspective and healing, while coaching is practical, action-oriented, and often infused with joy. If you’re ready to make dating feel more intentional, meaningful, and enjoyable, coaching might be the right path for you.

  • Connection Call: $45/session and you can book here.

    Individual Coaching Session: $195/session and you can book here. 

    Coaching Package (Five Sessions): $185/session and you can book here. 

    Coaching Package (Ten Sessions):  $175/session and you can book here. 

    Coaching Package (Fifteen Sessions): $160/session and you can book here.  

  • You may provide coaching support to a loved one by purchasing an electronic gift certificate.

  • We recognize that coaching and matchmaking services may not always be financially accessible. In certain circumstances, we offer accommodations on a case-by-case basis. To inquire further, please send us a message. For a more budget-friendly option, you may consider booking a Connection Call to discuss a specific challenge. If you are seeking free resources, we invite you to join our virtual Let’s Talk Dating discussion, where we explore key topics related to dating and relationships and listen to other members’ experiences.

  • “Our sessions have helped me realize how much I haven't been myself for the past three years. You helped me understand how I needed to shift my focus to caring for me before I could even start thinking of being a good partner to someone else. It's literally all thanks to talking with you. I finally feel like I'm making actual positive changes and in control of where I'm going."

    - EW, 20s

  • “I've worked with Kate for years. From the start she put me at ease when it felt like my life was spiraling out of control after the end of my decades long marriage. She’s a powerful "decoder" - helping me break down difficult situations and mapping out possible solutions. She has been a great help, allowing me to understand things that once felt beyond my grasp. I am extremely grateful to her."

    — MF, 50s

  • “Kate is amazing! I had been struggling with whether or not to leave a long, dysfunctional relationship and my sessions with her helped me finally make a decision. I returned to Kate later for coaching on how to start dating again because I felt like the whole dating world had changed since I was last in it. Kate helped me work through this stress and even connected me with others who were facing similar struggles.

    CS, 40s

“As a society, we have severely underestimated the importance of quality relationships, often prioritizing the accumulation of material wealth and status. Few of us were taught how to initiate and maintain healthy connections early in life. Consequently, our default approach may involve operating from a place of fear, control, or manipulation. This results in our relationships inevitably deteriorating, much like plants without adequate water. We may find ourselves navigating painful chapters - divorce, infidelity, custody battles - and often emerge embittered and exhausted. Regardless of your past experiences, you can make the choice today to begin educating yourself in how to pursue healthier connections, boundaries, and habits. It’s my life’s mission to assist people in this transformative journey, empowering them to prioritize and nurture themselves and the ones they care for most.”

Kate Woodward

Connection Call

Connection Call

Looking for a judgment-free space to share your thoughts and feelings? Book a Connection Call. This is your time to talk — we’re here to listen, offering encouragement without advice unless you request it.

This call lasts less than 30 minutes and provides an opportunity to connect with a certified life coach without having to commit to a coaching session or package. Cost: $45.