The Pros and Cons of Dating an Older Man
  • Posted Apr 25, 2014
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There is a fine line between hot and Hefner.  Recently we have seen the media portray age-gapped relationships in a variety of ways. With gossip staples like Courtney and Doug there are a variety of thoughts on these sometimes controversial relationships.


Dad or date?

Realizing your new boyfriend is just a few years younger than your father is a harsh reality.  Remind yourself what ignited this initial attraction and focus on that.  After all, there is something innately sexy about a silver fox.


He inevitably has a few years on you – professionally and personally.  You might love his deep pockets, but with his great power comes your vulnerability.  There is potential that you could never be financially equal to him, accepting this is key.


You may need to start skipping the traditional Thursday through Sunday bar scene with the girls to appease his lifestyle.  While this may seem like a much-needed break, there is potential for you to end up at a home-dinner party socializing with a group that may tell you about their son or daughter that is “just about your age.”  Awkward.  Try to create a balance.


Dating someone 20 to 30 years older than you means you’re probably going to see time take its toll in many ways.  When the allure of dating someone new wears off, it’s important to accept your partner for the person that you met – even if they are 20 years your senior.



An older man usually has an established work, social and home life.   As a younger, or transitioning individual, this stability may be exactly what you need.


Money honey!  Drinks, dinner, and gifts all on his dime.  Older men are often looking for something consistent. You can be sure that he won’t play games like millennials, since he’s past his prime player years.


The more experienced, the better.  Mature men have refined tastes, and that isn’t limited to his pallet.  He can show you things you never knew possible, and you can teach him that new trick you learned in Cosmo.


Older men are more old-school about courtship.  You won’t be dealing with the same texting, mixed signal bullshit that you’ve experienced in the past.


You’re going through something stressful?  Chances are he has been there too.  Advice and wisdom will be readily available from someone who isn’t your parent, but is equally wise.


You will never feel more wanted in your life.  Your body next to his will feel like a temple.  You won’t catch yourself with lingering thoughts of other lovers or competition.

Remember:  in the wise words of Aaliyah, “Age Ain’t Nothin’ But A Number.”

What’s your favorite thing about older men?

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