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6 Tips for Men Dating Older Women

By on January 29, 2015

When it comes to love, you can throw away the rule book because there are no real barriers to something genuine. Love will always trump issues of money, race and even gender. And yes, even age. As it relates to older women involved with younger men, there are still some taboos although they are quickly melting away. Thank you Usher!

Here are 6 tips for young brothers who want a May-December romance.

1. Older women generally are way ahead when it comes to honesty and frankness. They typically have nothing to lose by being and showing who they genuinely are and have had enough prior relationships to know ‘faking it’ doesn’t make it.

2. The older woman is also used to socializing and dating men. She was brought up to expect courtship, a man who shows interest. Real men will pay for her on the first date, even if she offers to pay her share or makes more than he does.  You just seem really cool when you do that for a real woman. Take care of her.

3. Don’t misrepresent yourself in any way to impress this woman. If you have a ‘baby mama’ you should say so, if you have a prison record, say so. Don’t surprise an experienced woman with down low drama of any kind.

4. Remember that when you are courting an older woman, she likely will have children in your age group. Be respectful of her status in life. Be interested in her kids as appropriate and when the time comes, be authentic about your intentions with their mother.


5. Do what you say you will do. Be consistent. Older women, especially women firmly in their careers, women who have accomplished a good deal in life, women of the world – they have seen the storyline and know only the players change. So, if you say you are going to call her then call. If you can’t then text her and make a plan for another time.

6. Neither one of you knows what’s ahead and if you get a vibe of desperation. Run. And you don’t want to be the one coming from a desperate place. Take your time.

Lastly, remember if a woman doesn’t respond to your first overture, it means she’s not that into you and you should respect that. Don’t become overbearing or disrespectful because things can quickly turn into a negative situation. And who needs that.


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