Case Study: How Holly Became a Pro at Starting Conversations

As a teacher in Chicago, Holly had never really “dated” before. 

She let her shyness rule her, and hadn’t felt ready for a relationship for a long time, focusing on her career instead of getting a date.

“I had just been doing online dating and wasn’t really actively looking for a relationship,” Holly said.

With online dating not getting the results she was looking for, Holly wanted to try something different. She enrolled in Confidence Connection Commitment with me because she felt like it was time.

“I wasn’t being intentional about my search at all. Then I did Whole 30 [eating challenge] and it changed my life. I felt better about myself and really good about the person I was – and I wanted to share that with someone because dating is just as important as your professional life.

You know, people always say that your job isn’t going to send you flowers on your birthday and other things like that, and they’re right.“

To start, I needed to know what Holly’s ideal dating life would look like. 

She told me that, ideally, she’d get asked out on the bus, get dates as she simply went about her day, and have a few fun date nights each week to look forward to.

But before that could happen, we had to understand why Holly wasn’t seeing these results in her life already.

Holly had worked with a therapist before, and so was somewhat aware of what was holding her back when it came to dating. 

She knew she was anxious and insecure when interacting with other people, especially men she liked. 

During conversations, Holly was very much inside her own head, wondering and worrying about what she could say to get the other person to go out with her.

This anxiety meant that Holly didn’t go out that often. And when she did, she put a lot of pressure on herself to meet someone and make it work out:

“Dating was very high stakes for me. This had to be the time I met somebody. And then usually for me, once I got up the nerve to go out, if it didn’t go well, I would go back into my shell.“

This carried over into her day-to-day life, where Holly would often walk around the city with her head down, avoiding eye contact and not engaging with anyone.

By not even making eye contact, Holly was missing out on all kinds of opportunities to meet and connect with new people-including men. 

She was giving off the vibe that she was closed off to new people and didn’t want to be approached – even though that was the opposite of what was true. 

No wonder she wasn’t getting asked out on the bus!

“When you’ve been living a certain way for a long time you just don’t question it. We have all these rules in our heads and my rule was just that I don’t talk to people.”

“I don’t talk to people” was a major mental block for Holly, so we focused on it first because it was having a huge impact on her day-to-day life:

“I would circle the aisle in the grocery store 10 times instead of asking for help.” 

We started with baby steps. The next time she was out, I told Holly to just talk to anyone. It didn’t have to be a cute guy – or even a guy at all. 

She just had to go up to someone and ask them something super simple, like where the coat check was, just as a way to start asking for help.

“I was out with my friends and nobody in our group would ask where the coat check was so I finally just did it. And it was a cute guy too, but that didn’t really matter because from then on it was like ‘oh, I can do this.‘”

This first step (and the ones that followed) helped Holly break free from this rule that she wasn’t supposed to talk to anyone. 

And that led to a huge transformation for her:

“I used to just walk around with my head down and I remember one day after I was walking on the street and someone was walking towards me. And I put my head down and I was like ‘Wait, I don’t do this anymore‘ and I put my head up because I just don’t do this anymore.”

With that internal pressure gone and Holly’s rule about “I don’t talk to people” busted, everything changed. 

After several baby steps, Holly was ready to attend a singles event, and we set a goal of talking to 5 different men that night. She actually ended up talking to so many men she lost count!

“I do still need to practice, but I’m so much better. Not just with men but with people in general. I got the mindset from Camille that starting conversations wasn’t about getting a date or getting him to like me but more like ‘Well why wouldn’t you talk to anybody and have a nice conversation?’ It completely enhances your life.”

She even ended up scoring a date at that singles event!

For Holly, the accountability of weekly coaching was definitely key to making these changes:

“For me, the accountability was huge. That’s where the big success was,” Holly said. “The fact that I did have to talk to Camille every week and that we were talking about relationships specifically. That’s where I had all these breakthroughs.”

Sometimes, we do need someone to hold our hand through the process and help us make the changes we need to make to get to where we want to go and achieve our goals. 

With something like dating – that nobody actually teaches you – this is doubly true.

“Camille is great. I keep calling her Hitch for girls because I love that movie but it’s true. She’s like a personal trainer for relationships and she works with you and customizes her offerings to what you need to work on.”

Holly now has a whole new outlook on life and is starting conversations everywhere she goes. Her confidence is through the roof, and “I don’t talk to people” is a thing of the past.