Anna Jorgensen
Dating coach for men, from a woman's point of view
| Hourly rate range | $75 to $150 an hour |
|---|---|
| Focus areas | Dating for menApproach anxiety and confidenceTexting and first datesMatchmakingConfidence and self-esteem |
| Works with | Men |
| Also coaches | Life coach |
| Practice | Wingmam |
Anna Jorgensen is a dating coach for men. She runs Wingmam and teaches men how to understand women, build confidence, and find lasting relationships. Anna spent 20 years in real estate sales before she became a dating coach and matchmaker in 2012. She has interviewed hundreds of singles and couples about dating. Her YouTube channel has 400,000+ subscribers, and she also runs a community of 2,700 active members.
What Anna helps with
Anna helps men who want to understand women and date with more confidence. She teaches direct, honest dating skills and does not use scripts or games.
- Telling when a woman's interest is real or fading
- Understanding why women act hot and cold
- Building confidence without arrogance
- Leading in dating without losing yourself
- Knowing when to walk away
- Overcoming Nice Guy Syndrome
- Knowing what to say to women
- Getting out of your head when talking to her
Who Anna works with
Anna works with men who want a real relationship and not just casual dating. Her viewers come from more than 50 countries. Her clients include men in Vancouver, the U.K. and the U.S. Some are re-entering dating after time away.
How Anna works
Anna teaches through weekly videos, a blog, and a Level Up Challenge program. She also offers one-on-one coaching. Her free Instant Confidence cheatsheet uses a five-sense trick to help men stop overthinking and start conversations. She has a private community with 2,700 active members.
Background and qualifications
Anna grew up in remote logging camps in Western Canada. She was very shy as a young adult and went into real estate sales. She worked in sales for 20 years and studied adult behavior along the way. In 2012 she left real estate to become a dating coach and matchmaker. She has studied thousands of hours of dating and relationship books, videos, and courses. She has attended dozens of workshops and seminars, and interviewed hundreds of singles and couples. She has also written a memoir.
Anna Jorgensen pricing
Programs and services
- One-on-one coaching
- Level Up Challenge
- Online community
- Free Instant Confidence cheatsheet
- Weekly YouTube videos
Anna Jorgensen reviews
The CoachVouch take
A former real estate executive who coaches men on dating from a woman's point of view, with a YouTube audience of 400,000+.
Best for men who want honest advice on women and a lasting relationship instead of pickup tactics.
Common questions
How much does Anna Jorgensen charge?
Coaching with Anna runs $75 to $150 an hour. Message Anna from this page for an exact quote.
What does Anna Jorgensen help with?
Anna Jorgensen helps with telling when a woman's interest is real or fading, understanding why women act hot and cold, building confidence without arrogance and leading in dating without losing yourself.
Does Anna Jorgensen teach pickup tactics?
No. She teaches men to date without games, scripts, or pretending to be someone else. Her focus is on getting a girlfriend and building a lasting relationship.
Does Anna Jorgensen offer one-on-one coaching?
Yes. She offers one-on-one coaching along with her programs and online community.
How do I contact Anna Jorgensen?
Send Anna a message from this page. It's free and takes a minute.
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Last updated September 2026. Request a correction.