The Short Version: Based in Vancouver, Anna Maria Jorgensen, aka the Wingmam, has a talent for inspiring confidence in daters seeking to change their love lives for the better. Her personalized counseling helps shy, inexperienced, and uncertain singles understand how to attract the right person and date successfully. By sharing practical advice on matters of the heart, Anna gives her clients the tools, strategies, and knowledge to navigate dating, both online and in person, and get the results they want. Additionally, Wingmam’s engaging dating coaching programs prepare single men and women to date with confidence and find fulfilling relationships. With hands-on coaching, Anna brings clarity to how dating works in the real world and what you can do to reach your own happily ever after.
Dating coach Anna Maria Jorgensen, known in Vancouver as the Wingmam, knows how to talk singles through dating issues and bring out the best in her clients.
One single man in his early 40s came to her hoping to change his dating patterns. He felt demoralized from going on so many first dates and never getting to that second date. He was in the tech industry, successful, and commitment-oriented, but he had low self-esteem in terms of talking to women. Anna told him it was just a matter of practice and knowing what you want. She went on a mock date with him and gave specific feedback on what he could do differently.
Within a few weeks, the man met a beautiful woman whom he thought was out of his league. Normally, he would’ve given up on the date, but Anna encouraged him to give it a shot and believe in himself. Along the way, the dating coach advised him through some texting conversations, explaining what to say and why. Eventually, he got to the point where he could’ve escalated the relationship with the woman but chose to break things off because he realized they didn’t want the same things in life. She was seeking a casual relationship, and he wanted something more meaningful and lasting.
“That’s one of my favorite success stories,” Anna said, “because it started with him feeling not good enough for his date and ended with him choosing not to continue with her because she wasn’t right for him.”
In her work as a dating coach, Anna inspires many personal revelations for clients seeking to grow and improve in the dating scene. For men to get started, you can take a page out of her playbook by downloading the Free Cheatsheet: Instant Confidence “Talk to Her” Technique, an introductory guide on what to say to a date.
Anna lays out a bold strategy to overcome the fear of rejection and land a date with any woman who catches your eye. Through comprehensive online courses and personalized one-to-one coaching, she gets singles where they need to be to find love.
“My foundational courses are about understanding the opposite sex and becoming more attractive,” she said. “I don’t want anyone becoming reliant on me. I give daters the tools to do it on their own.”
How a Local Real Estate Agent Became a Perceptive Dating Expert
Over 20 years ago, Anna began her career as a real estate agent in Vancouver. She took a personal interest in helping her clients and often offered advice on a variety of subjects, not just where to live. One day, a former client wrote to thank her for giving him relationship advice because it had led to him having a better dating experience. He said he was engaged to be married and very happy that he took his real estate agent’s relationship advice to heart.
This was a huge confirmation for Anna that she had something valuable to say to singles and could make a difference in their lives. She decided to learn more about the ins and outs of dating so she could teach single men and women as a professional dating coach.
She began by writing love advice online and then transitioned to rewriting dating profiles for men. Today, she has a full-blown personalized coaching service for singles seeking love.
Anna told us, as a matchmaker, she uses a lot of the people skills she learned as a real estate agent. “It’s mainly psychology. A lot of it is understanding what people want versus what they think they want,” she explained. “You have to know what’s the why behind it.”
In both lines of work, Anna learned to see beyond a person’s list of qualities and criteria to get to the heart of what people truly wanted. Whether you’re searching for a dream home or a long-term partnership, having that objective eye to assess what actually fits your needs can be very helpful to anyone on the market.
“Changing behavior is difficult. You need to have some skill in the persuasion department to help people arrive at decisions that benefit them,” Anna noted. “Once they agree to the change, it’s easier to get the person to take the action that’s best for them in the real world.”
Foundational Coursework & Personal Sessions on Getting a Date
Anna’s approach to dating coaching is all-encompassing. On the Wingmam website, she has an array of dating resources for men to boost their self-esteem and help them become more attractive to the type of woman they desire. Her products include step-by-step modules and impactful real-world challenges to help men develop their dating skills. For instance, the dating coach’s Double Your Online Dating Training is an online program focused on how to find (and woo) the right woman online.
WakeUP2Luv, aka Get a Girlfriend Guaranteed, is a comprehensive coaching program that guides men to become the best version of themselves and take specific actions to attract a compatible date. By taking this online course, you’ll learn the five must-have qualities of successful daters and what it takes to build a lasting committed relationship.
Anna also offers supportive dating services for women, most notably the Get the Guy Guaranteed program, which walks singles through overcoming insecurities, being receptive to love, and attracting the man of their dreams.
And, of course, her one-on-one coaching services are available to back up singles in need of personalized advice or recommendations. Anna knowledgeably helps people define their dating objectives, create a targeted strategy, and pick a partner with compatible values. She emphasizes in her coaching that, to create outward dating success, singles must first look inward and understand what attractive qualities they bring to the relationship.
“My ultimate goal is to get you to become the best you,” she said. “Whether you need help being assertive or just don’t understand what you’re doing wrong on dates, I can help you learn, grow, and achieve your goals.”
Testimonials From Singles Who Transformed Their Love Lives
Throughout her career, Anna has received glowing praise from the single men and women she has coached and counseled. Her proactive advice makes singles feel better-equipped for an ever-changing dating world. Her central message to singles is that it’s on them to make improvements in their lives. “You only have control over yourself,” she said, “so any change has to start with you.”
“I definitely feel something shifted inside me,” said D.K. in a testimonial. “I feel greater confidence, and I can see and feel that I am attracting more attention from the opposite sex.”
“You gave me some good advice years ago that helped with my perspective on dating. Since then, I’ve had healthier relationships with women.” — Steve F., one of Anna’s former clients
The Wingmam programs pack a lot of information into an accessible format, empowering singles to fix their relationships on their own. Some have written positive reviews to thank Anna personally. “I enjoyed how easy it was to listen to the audio,” said M.C., an anonymous client who took the WakeUp2Luv program. “You had me engaged and committed throughout. I like the wholeness of the program.”
Anna loves hearing back from the people she has helped over the years. “I live vicariously through my clients’ successes,” she said. “It’s the biggest high. I love it.”
Wingmam: Effective Coaching For Adults Seeking Commitment
Anna works with all types of people, from shy nice guys to high-achieving women, on developing the dating skills to attract the partner of their choice. For many clients, her words of encouragement come at just the right moment and inspire them to turn their dating lives around. With a deep understanding of modern dating dynamics, Anna enlightens daters on how they can make positive changes in their love lives.
Currently, Anna is developing a local matchmaking program to further help Vancouver singles make deep connections with one another. Through a range of dating services, the Wingmam aims to give daters everywhere the solutions they need to realize their dating potential and get in the relationship of their dreams.
“Mainly, I want to encourage singles not to give up,” Anna told us. “It’ll happen when you let go. Just don’t give up.”