The Scoop: Since 2010, Anna Maria Jorgensen has offered herself as a resource to single men and women wondering what the heck the opposite gender is thinking. Anna became known as Vancouver’s Wingmam thanks to her encouraging and supportive take on dating coaching. She has provided singles with consistent guidance and action-oriented advice to help them get the results they want in the dating arena. Today, Anna has expanded her business model from online and phone coaching to include a text-based coaching program that will give clients access to targeted advice whenever they need it.

Anna Maria Jorgensen took on the name “Wingmam” because her goal is to support singles throughout the ups and downs of dating. In 2012, she founded a dating coaching business in Vancouver and began taking on clients throughout Canada and the US by scheduling one-on-one sessions over the phone.

But sometimes her clients had an immediate issue — maybe a love interest had sent an ambiguous text or a date hadn’t gone as planned — and they needed to talk to their Wingmam before their scheduled sessions. Anna realized that some singles needed more than a weekly or monthly phone call — they needed someone on call to truly back them up in times of need.

Photo of Anna Maria Jorgensen, dating expert

Anna Maria Jorgensen, aka Vancouver’s Wingmam, gives action-oriented dating advice to clients.

That’s why Anna has started offering a new coaching-by-text package to clients who want affordable, accessible dating advice while on the go. This flexible plan has shaken up her business model and given singles the resources they need to succeed.

Anna told us text coaching appealed to her because it helped her become more available to her clients when they needed her, and it gave her more time for herself.

New clients start with a get-to-know-you phone session during which Anna assesses their individual needs and comes up with a game plan. She meets regularly with her clients over the phone or via Skype and often gives out homework so they can continue learning and growing between sessions. The standard coaching package includes impromptu maintenance calls in case an emergency situation arises. Now her texting program will further guide and support singles in the modern dating scene.

“My business motto is ‘For when you want to settle down without settling.’ And my personal motto is ‘Love is the answer,'” she said.

Anna’s philosophy of self-love and self-care has impacted the lives of many clients over the years. She is a positive influence on single men and women, bolstering them with a Pollyanna-like optimism and, at the same time, telling them what they need to hear in uncensored and unreserved sessions.

“If I can help people find that place within themselves where they know deep down that they complete themselves,” she said, “they’ll be happier and ultimately way more attractive.”

Inspiring Clients to Take Action & Understand Dating

Anna recently launched a Coach by Text program (also known as the “Hitch” program) to provide real-time advice to a limited number of coaching clients who want to talk to an expert while navigating the dating scene. These clients can text her while they’re at home, going on a date, or flirting at the bar.

Basically, any time they have a question, they can fire off a quick text, and Anna will have an answer for them.

“You gave me some advice years ago that helped me have better relationships, and now I’m getting married.” — Steve F., a former client

For instance, if they go on a great date and want to know when and how to text or call that person, they can tell Anna what’s going on and get her advice about what they should do and why. She provides simple, action-oriented recommendations coupled with the reasoning behind her advice. She wants her clients to understand the philosophy behind attraction and love so they can make good decisions on their own in the future.

“The goal is to teach them how to fish, not to supply the fish, so that eventually they don’t need me,” she said. “When I feel that the client is ready, I’ll start asking them to give me their suggestions (and why) on how to handle the situation. Then I provide feedback before they take action.”

Working Closely With Shy Guys & Boss Babes

Clients hiring Anna get her full attention. She doesn’t spread herself too thin or try to take on more clients than she can reasonably help. She said she tends to work with no more than 10 clients at a time. “I’m not trying to get rich or famous, so that’s enough for me,” she said candidly.

Many of the men who turn to Anna’s coaching programs are introverted singles who can be socially awkward or painfully shy. These men can relate to Anna, who is a proud introvert, and find her encouragement boosts their self-esteem. By giving her honest advice, she can help her clients figure out what’s gone wrong in their previous relationships and how to avoid those mistakes in the future.

While the men in her client base tend to be taciturn and timid, the women who work with Anna often have no trouble speaking their minds. She described her typical female client as an empowered woman who is confident at work and secure in herself. However, these “boss babes,” as she calls them, can intimidate dates and lose touch with their femininity. She teaches them how to attract the type of men they want to date and become more capable in the dating scene.

“I definitely feel something shifted inside me,” said Deni. “I feel greater confidence, and I can see and feel that I am attracting more attention from the opposite sex.”

Anna requires her clients to take her online program WakeUp2Luv while working with her because it helps them invest in self-development and improve in their own time. The six-week program supplements her coaching and allows clients to pursue a greater understanding of sex and dating.

This comprehensive course benefits singles who feel uncertain about matters of the heart and want straightforward advice. Anna said some clients learn everything they need from the online program while others want to discuss the takeaways in personal coaching sessions.

“Anna’s reasonably long program would be beneficial to any man who’s looking to get serious about dating,” said Mike S. in a Yelp review. “Anna has the ability to communicate with men while promoting the positive cause of love.”

Text Coaching Has Been a Great Success So Far

Anna said her first text coaching client was a single man intent on winning back his ex. “When he contacted me, it was the perfect opportunity to test out the idea,” she said, “which I’m glad I did because I discovered that I get really invested in the client.

In addition to sending him encouraging texts, Anna put in a lot of extra hours creating advice videos with him in mind on her WingmamTV YouTube channel. She also sent him useful information about dating, relationships, and breakups.

Over the next six weeks, Anna offered the man her expertise, and he took her advice when trying to reconnect with his ex-girlfriend. While the ex did come back, Anna said the greater success was in getting her client to realize he was a catch and worthy of love. His confidence soared, and he took control of his love life in a way he hadn’t before, choosing to move on. He’s now with a girl he calls “a perfect 10 in every way.”

“In addition to learning more about myself, it was great that you spelled out what men want in a relationship.” — Cathy S., one of Anna’s clients

Anna’s clients often say in testimonials that they have gained a more positive outlook by working with the dating coach. Her insights lead singles to have epiphanies about what they truly want and how to get it.

“You pulled me through the hardest thing I’ve ever felt,” said Steffan W. in a testimonial. “I appreciate you and what you have done for me. I feel like you took my case personally.”

Vancouver’s Wingmam Makes Coaching Cool & Fun

When Anna puts together her coaching programs, she carefully weighs the needs of her clients and thinks about what she can do to offer practical and healing guidance. Her text coaching program is an innovative and effective way to reach singles when they most need someone to talk to.

Whether she’s creating an advice video or having a healing conversation over the phone, the Wingmam is always there to support daters through personal difficulties. She told us she hopes hiring a dating coach will become normalized as more singles decide improving themselves is the most worthwhile thing they can do with their time and energy. “Perhaps hiring a dating coach will become the new cool thing to do,” she said with a laugh.

While the Wingmam doesn’t have any specific plans for the years ahead, she will surely be on the lookout for creative coaching methods and cost-efficient tools to get singles up to speed.

“Mostly I care about making an impact on my clients’ lives,” she said. “Personally, I applaud anyone who chooses to better themselves, and whomever they choose as their coach — there are a lot of great coaches in the industry — if they get happier, the world gets happier, and we all benefit.”

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