How To Flirt With Older Women [Video]

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

How to flirt with older women tips applies to younger men seeking older than them women as well as older men seeking women around their own age.

As a woman close to 50 I’ve had a relationship with a man much older and one much younger than I am.

I can def definitely tell you how to flirt with older women!

Men wanting to date women older women must realize ladies hide behind a bitterness blockade do so with good reason.

Getting past her fortress isn’t insurmountable.

Let’s get right to the point …


  • Watch the video.
  • Be bold and ballsy.
  • Repeat (a) & (b) as necessary.

How to Flirt with Older Women Takeaways and Bonus Tips

  1. Women are turned on by men with courage. 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 good reason: other dud(e)s have disappointed and/or damaged them. Not your fault but, yeah, now you have to deal with it.
  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’ve got to start as her knight in shining armour.
  4. You can break down her wall and protect her from perceived pain by starting 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 (at least while they’re young), they’ll get plenty more with an attitude of gratitude than one of entitlement.
  5. Remember: you’re her hero. Act like it and Sam’s your uncle! 😉


Being her Knight doesn’t mean acting like a Pawn! The trick is to know how to lead without becoming a doormat.

My playlist on Why She Tests and How to Handle Her Tests will help but if you’ve even been called Too Nice then start with my No More Mr Nice Guy playlist.

Attract Older Women Playlist

Nice Guy Playlist

Why She Tests Playlist

About the Author Anna Jorgensen

Vancouver dating coach for men who love women! ❤️ (Not PC and not a feminist.)

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1 comment
Randy H says August 7, 2020

Always wise, experience-based, smart, and useful. One of two advice advisors I value most. And the only gal.

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