How To Flirt With Older Women [Video]

Q: Is How to Flirt with Older Women the Same as How to Flirt with Younger Women?

I’m a woman over forty and I’ve had a long ish term relationship with a dude who was much younger than me, so this is first hand experience and I can def definitely tell you how to flirt with older women!

Men wanting to date women over (or under) 40: ladies behind a bitterness blockade have good reason for erecting such walls.

Getting passed her fortress isn’t insurmountable.

This post is mostly for the fellas, so I’ll get right to the point …


  • Watch the video.
  • Grow some (balls).
  • Repeat (a) & (b) as necessary.

The Takeaways and Bonus Tips (just the tip?):

  1. Women are turned on by men with balls. As in: guts. Pretend you hear Sam Elliot saying, “No guts, no Glorias.”
  2. Single ladies over 40 (or not) may be supplementing their lifestyle with “the bitter pill” with damn good reason: other dud(e)s have disappointed and/or damaged. Not your fault but, yeah, now you have to deal.
  3. The sooner you get over it—this erection: her wall—the better you’ll feel. Consider it a welcome challenge. If you want to become her king, you gotta act like her knight in shining armour.
  4. You can break down her wall and protect her from perceived pain with authentic sincerity in your approach and understanding in your interactions. Even though men—unlike women—need sex as much as they need food, water, sleep, they’ll get plenty more with an attitude of gratitude than one of entitlement. (Yeah, that’s part of what I teach / preach and is too much to cover here.)
  5. Remember: you’re her hero. Act like it, and Sam’s your uncle! 😉


Questions? Input? Any fellas got the guts to share a short story about a successful or “failed” attempt at a worthy woman’s wall? Comment below!


About the Author Anna Jorgensen

Vancouver Dating Coach for Shy Guys & Introverted Men. Matchmaker Liaison. Founder: Wingmam

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