Dating coach Wonder Hollingsworth has built her work around a part of modern relationships she says is often overlooked: dating itself. In a culture where conversations tend to focus on commitment and long-term partnerships, Hollingsworth centers her approach on the decisions, behaviors, and boundaries that come before a relationship begins.
In this interview, Hollingsworth explains the distinction between dating and relationships, discusses common patterns that affect how people connect, and shares guidance on communication, self-awareness, and confidence. She also reflects on her role as a podcast host and why she believes clarity and intention matter at every stage of dating.
First, let’s start at the top. Of all the paths you could have chosen, why did you decide to become a dating expert? And how does that differ from being a relationship expert?
I chose to become a dating expert because I noticed there was a lot of conversation online about relationships, but very little focus on dating itself. People talk about what happens once you’re already in a relationship, but they rarely talk about the steps that lead there.
I believe the way you date determines the outcome of your relationships. Dating is just as important as the relationship itself, yet it’s often overlooked. Through conversations and research, I realized people didn’t fully understand how critical the dating phase is, so I decided to focus my work on educating and bringing awareness to that.
Today, there’s a lot of confusion between dating and being in a relationship. Can you explain the difference?
Dating is about collecting data. You’re gathering information to see whether there’s potential for a relationship. I look at relationships as the umbrella or the entity. Friendships are relationships. Situationships are relationships. Even the dynamic you have with coworkers is a type of relationship. Dating is one part of that umbrella, but dating does not automatically mean you are in a committed relationship.
What patterns do you see most often when people struggle to form or maintain relationships?
Many people are dating from unhealed places. When a relationship ends, they don’t pause to reflect or build self-awareness before jumping into the next one. Some people struggle with being alone. They don’t give themselves time to process what went wrong or what lessons they learned. Pausing between relationships is healthy, but a lot of people skip that step.
How should people approach dating apps if they want clarity about their goals and boundaries?
The first step is assessing your dating style. There are many different styles. Some people date with intention. Others are serial daters who enjoy dating without commitment. Before joining an app, you should know what your dating style is. It’s okay if that changes over time, but you need to be honest about it. Many people date without knowing what they want, what they’re looking for in a partner, or how they want the experience to feel. That clarity should come before signing up.
What role does communication play early in dating, and what mistakes show up first?
You need to understand your own communication style and learn the other person’s style as well. Some people prefer texting. Others prefer phone calls. If you like someone, see whether you can meet in the middle. Flexibility is important. Communication matters, but so does knowing what works for you and whether the other person is willing to adapt.
How can someone tell the difference between chemistry and compatibility?
Chemistry is a feeling. It’s that immediate attraction or connection where you feel drawn to someone. Compatibility requires deeper, more detailed questions. You have to ask about values, character, and morals. That’s how you determine whether someone is truly compatible with you. Chemistry may spark interest, but compatibility sustains a relationship.
You’re also a podcast host. What inspired you to start the podcast?
People connect in different ways. Some respond to posts or written content, but others want to see and hear you. They want to know how you speak, how you move, and whether you’re relatable.
I co-host the podcast with Walter Frye. Having both a male and female perspective was important to me. We have gender-neutral conversations and focus on self-awareness rather than blaming one side. We also bring licensed therapists onto the show because there’s a clear line between coaching and therapy, and we’re intentional about respecting that.
Is there ever a conflict between your role as a dating expert and your personal dating experiences?
I haven’t dated in over five years, so I don’t have current dating experiences to compare. Because I’m not dating right now, I haven’t encountered conflicts in that area.
What advice do you give people reentering the dating scene after a long break or breakup?
They need to make sure they’re ready. People often ask, “How will I know?” The answer is trust yourself. If you’re able to make decisions in other areas of your life but don’t trust yourself when it comes to dating, that’s a sign to pause. Ask yourself why you feel uneasy or nervous. Self-trust is key before getting back out there.
How should couples handle disagreements in the early stages?
While you’re dating, ask how someone handles conflict. Give scenarios and examples and see how they respond.
If you don’t ask these questions early, or if the answers don’t align with what you consider a green flag, that tells you a lot. How someone handles conflict should be part of the conversation before entering a relationship because it sets the foundation.
How do social media and texting shape dating behavior, for better or worse?
For worse, it’s not organic. People observe each other online instead of engaging in real-life interactions. You watch what someone posts, how they behave, and it removes the natural experience of meeting someone in person.
For better, I’d say it can help people who are shy. But overall, I don’t see much positive impact. Social media often creates delusion and illusion when it comes to dating and relationships.
Last question. What practices help people make decisions about commitment with confidence?
Knowing your self-worth. Believing in what you deserve and setting boundaries upfront. You have to think it, feel it, say it, and believe it. When you know your worth and set clear expectations, you attract partners who align with that. Belief and intention matter.
Be’n Original
