A Speaker Who Doesn’t Just Talk About Relationships. She Gets the Whole Room Talking.

Speaker Cheryl Dillon delivers engaging talks and interactive experiences that help audiences rediscover the joy of genuine human connection.

Cheryl Dillon brings warmth, humor and fresh perspective to conversations about the relationships that matter most, what helps them thrive and what can get in the way.

Her highly interactive presentations blend storytelling with audience participation, getting people talking, thinking and laughing while sharing practical tools they can put to use right away.

Featured Talks:

Cheryl’s presentations are tailored to each audience.

  • The Little Things That Make Love Last: What Happy Couples Do Differently

    (Ideal for couples’ events and retreats)

  • Dating Without the Job Interview: How to Actually Get to Know Each Other

    (Ideal for singles’ events and dating events)

  • Real Adult Friendships: How to Make, Deepen and Sustain Friendships That Last

    (Ideal for women’s conferences, retreats, personal growth audiences)

  • From Small Talk to Real Talk: The Power of Genuine Connection

    (Ideal for conferences and general audiences)

  • It Starts With You: Becoming Your Own Best Friend

    (Ideal for women’s groups, personal growth audiences, wellness communities)

  • Beyond The Business Card: The Networking Mistakes Most Professionals Don’t Know They’re Making

    (Ideal for networking groups and chambers of commerce)

Topics Cheryl Explores:

  • Why some relationships bring out the best in us while others bring out the worst.
  • The little things strong couples do differently, and the habits that can slowly wear a relationship down.
  • Why dating can feel like a job interview and what actually helps two people get to know each other.
  • Why adult friendship can be so dang hard, from finding your people to keeping great friendships strong.
  • Why some conversations click while others leave us wondering, “Why am I doing all the work here?”
  • The expectations, assumptions and stories we bring into our relationships without even realizing it.
  • Why the relationship you have with yourself changes the relationships you have with everyone else.
  • Why traditional networking often feels so awkward and what actually helps turn a new contact into a genuine relationship.

What Audiences are Saying

Cheryl’s talk on the Power of Genuine Connection was one of the most fun and interactive presentations we’ve had at Rotary. She has a rare ability to speak straight to the heart – her humor, authenticity, and practical wisdom left me with a new perspective on how I show up in my conversations. I’d recommend her to any group looking for a speaker who helps people truly connect while having fun doing it.
Gayle Tweedy, Rotary Club of Carlsbad
I’ll be honest, when Cheryl started leading us through some of the exercises, I wasn’t sure what to expect. It felt a little outside my comfort zone at first. But once we got into it, the value became crystal clear. Two months later, I’m still using what I learned that day in my conversations.

Cheryl has a gift for making practical, meaningful skills genuinely accessible, and even fun. I’d recommend her to any group that wants to walk away with tools they’ll actually use.

Brian Crumbaker, Rotary Club of Carlsbad

Cheryl’s presentation was fabulous – engaging, practical, and honestly a lot of fun. She gave us real tools for going beyond surface-level chatter and building genuine connections, from how to ask better questions and remember the details that matter, to how to gracefully exit a conversation with someone who can’t stop talking about themselves.

I made a new connection right away during the exercises. If your organization is looking for a speaker who is warm, funny, and genuinely changes how people interact with each other – invite Cheryl.

Vicky Kvitek, Woman's Club of Carlsbad

Cheryl’s presentation was both inspiring and useful. She walked us through several techniques for remembering names and personal details – the kind of tools that actually change how you show up in a conversation.

I left with specific strategies I’m already putting to use.

Carolyn Hammel, Woman's Club of Carlsbad

I’ve always wanted to be a better conversationalist, but I didn’t know where to start. Cheryl broke down the actual mechanics of building a real connection with someone you’ve just met. She’s enthusiastic, relatable, and so easy to listen to. I’d recommend this to anyone who wants to communicate more deeply and move past surface-level relationships.

Victor, Carlsbad Senior Center

I noticed I was always the one asking questions while conversations stayed frustratingly shallow. Cheryl changed my perspective on why that happens and what to do about it. Delightful speaker. Just about everyone could benefit from this.

Terri, Carlsbad Senior Center

I recently moved to Carlsbad and was looking for ways to get closer to people. Cheryl gave me real tools for doing exactly that. She’s warm, funny, and so sincere. If you want to deepen even a casual acquaintance into something more meaningful, this presentation is for you.

Laura, Carlsbad Senior Center

Funderful in Action

Media & Conversations

Featured Conversations:

Not Your Mother’s Midlife Crisis

Key Points in the Divorce Process Through Mediation & Coaching

Radiantly Rooted with Rachel

The Secret to Deeper Connection in Midlife, Starting with You

The Midsters

Cultivating a Joyful, Funderful Life

Reinvention Real Talk

Choosing Yourself in Midlife

Having Cheryl on my podcast was such a joy. She’s genuine, kind, and brings this lovely, grounded energy that makes the whole conversation feel easy.

Anne Marie Costanzo, Aging Fiercely Podcast

Book Cheryl

Cheryl delivers the kind of presentation that feels more like a great conversation with a friend than a lecture, with plenty of substance tucked inside the fun.