Case Study: How a Single Mom Went from “Not Even Looking” to Getting a Date

When Ana started coaching with me, she was a single mom, studying for her Ph.D., who hadn’t dated in over five years. 

She really wasn’t looking for help dating and was more interested in improving her social skills in general.

“I started working with Camille not to talk to men necessarily, but to be able to talk to anyone. In the future I’m heading towards — being a professor, and a business owner, and a writer — I wanted to make sure that, when I finally reach that dream, I’m able to communicate with and connect to other people.“

She knew that her current anxiety around conversations wasn’t serving her in her work life or in achieving her life goals. 

And with her son getting older, she started to think it might be nice to have a relationship.

“Now that my son is 3 I feel like I’m a little bit more able to just go out. I don’t feel so stuck at home anymore. And there’s a part of me that’s like yeah I want a partner I want someone, you know, come home to and to share the bills with, but my son is what I care about the most.”

Ana had been to one of my in-person flirting classes in Chicago. 

Initially, she had thought she was open to dating, but after the class realized that, even in her head, she was being very harsh in her communication with other people.

Ana loved my philosophy of “leading with the sweetness” when talking to people and realized there was a lot she could improve.

“I have this side business I want to launch, where I’ll be talking to parents and kids. And I’m working on my Ph.D., but I don’t come across as very confident or very outgoing.“

Ana’s problems connecting with others mostly revolved around how she was communicating with them. 

She was coming across much more harshly than she thought she was, she would dominate conversations out of nervousness, and she felt like she couldn’t talk to men with confidence. 

She’d share everything right away, trying to be upfront and honest, and instead ended up being overwhelming.

“One of my issues was that I would just say everything. I wouldn’t stop to take a breath or let him speak, I’d just lay it all down for him. So after an hour-long conversation, I’d feel like ‘OMG, I gave him my all and this guy didn’t call me back!’ and it was really disappointing.”

That disappointment wasn’t the only emotion Ana and I had to work through. 

She also had some mental blocks and anxiety around initiating conversations and talking to people.

“I was caring too much about people looking at me approaching other people and thinking that they would think I was weird. But then I realized that, when I look at those people, I don’t think they’re weird, I think they’re interesting. Those are the people you kinda want to be friends with because they know everybody.“

Even though Ana wasn’t focused on dating, our main focus for our coaching was really on flirting with guys. 

Not because I wanted to change her mind about dating or push her to date, but because flirting is all about communicating with other people in a light-hearted, fun, and open way.

“At first I didn’t get it, it didn’t make sense to me why Camille wanted me to compliment other women but once I started doing it, it sort of clicked for me. It’s not about flirting to get a date. It’s about saying to people that you’re open to having a conversation and letting them know that – and that change is huge.”

Flirting is really just connecting to someone else in the present moment, which is why it was perfect for Ana. 

Overthinking was a major problem for her, and in work situations she’d freeze up and not say anything, particularly in meetings. 

If she was going to be a professor and a writer and a speaker, this was something she needed to overcome.

By helping Ana learn more about herself and turn her focus on becoming a confident woman, she got more comfortable around other people and stopped overthinking things as much.

“Now at work I just say whatever pops into my head. Like, sometimes it’s super professional and sometimes it’s not the perfect thing to say, but I still say it because it’s better than saying nothing.“

But her most unexpected result is that she’s actually found a guy! 

One of the exercises I had her do was go to a singles event and talk to eight men. It could be a brief convo, or more in-depth, but I wanted her to start conversations with eight different men that night, just to practice.

“I went out and I truly had no expectations that night (and there’s usually some ‘oh my gosh, is this gonna be the time when I meet him?’ going on in the back of my head).

Then I got there and there was this guy standing over there on his phone. I went up to him and was like ‘Hi, my name’s Ana’ and we ended up talking for over an hour. And when he had to leave I was like ‘are you gonna take my number or not?”

This alone was amazing progress for Ana! 

She was feeling comfortable enough to have real conversations instead of over-sharing everything. But Ana went even further than that…

“Even when he left I continued to talk to men because, like, I had a quota. I had to talk to eight men and I ended up talking to 13.“

This was amazing, and I was so thrilled for her! Through these conversations and changing her communication style, Ana started to change how she saw relationships.

Ana used to be very black-and-white with her relationships in the past. 

If she didn’t like something (like smoking) it was a dealbreaker and the guy was gone. But she started to see that dating is a learning process — both for her and for him.

“I started realizing that it’s a learning process not just for me but for the guy, too. We’ve been giving each other opportunities to say ‘I don’t like this about you. It’s kind of a deal breaker for me.’ But I’m having more of a conversation than I would have before. We’re sort of saying, like, ‘let’s see how much we can be together and get to a point where we’re okay’.“

But the best part (and the part I’m the most excited about) is that Ana feels this way:

“The cool thing about Camille’s coaching is that I know that if I found a guy who likes me just exactly as I am once, I can do that again.”

And that deep knowing that she has the skills to attract the kind of man she wants is priceless.