Will Older Men Date Independent Women

Women's Dating

Will Older Men Date Independent Women?

Sam Stieler

Written by: Sam Stieler

Sam Stieler

Sam has been writing about dating and relationships for more than three years now. He holds a bachelor's degree from Bucknell University, has self-published a few of his own books and is currently working on mastering the double right turn in his salsa dancing classes.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Older men and younger women have a lot to offer each other when it comes to dating, but they also have a few potential obstacles to find their way around en route to a happy relationship.

Even though our culture is fairly accepting of older men dating younger women, both members of the relationship will need to endure their share of name-calling, all while debunking a litany of unfair assumptions tossed at them from strangers and loved ones alike.

But aside from dealing with the outside pressures and social stigmas you may face while dating an older man, will you need to face any internal challenges unique to your May-December romance?

Culture clash.

The biggest concern young women feel when dating older men isn’t the age gap between them, but rather the generation gap separating them. Men and women born 20-plus years apart from each other grew up during different eras and learned different rules and expectations regarding what roles men and women play in each other’s lives.

Perhaps the greatest dissonance younger women fear when dating older men lies in just how independently women are supposed to live their lives. While plenty of younger women like the thought of dating older men, few young women want to give up their independence to do so.

But is this really a valid concern, or is it ultimately unfounded?


“You may find the older man is more

supportive than the younger men.”

How old are we talking?

If you’re looking to date a man who is 70 years or older, a man who grew up in the 1930s or 1940s, then you would do well to make sure the two of you share the same gender-role expectations before considering a relationship.

But if your “older man” is in his early 60s or younger, then you probably don’t have anything to worry about.

Think about it.

  • A man around 60 was a teenager in the 60s and a young man in the 70s.
  • A man around 50 was a teenager in the 70s and a young man in the 80s.
  • A man around 40 was a teenager in the 80s and a young man in the 90s.

The majority of older men you’d consider dating grew up after women began to fight for, and win, key battles in the war for equality.  The majority of older men you’d consider dating formed their opinions about gender roles during times when female independence was an important element of the culture.

So don’t worry — your desire to live your own life won’t be any more shocking to a man between the ages of 40 and 60 than it is to a man between the ages of 20 and 30. In fact, older men might be more supportive of your desires for independence than younger men.

The personal security of older men.

To a certain extent, you will find yourself in competition with young men, including the young men you date. Young men are often insecure, unsure of themselves and their worth and are hounded by a vaguely defined fear that they’re making the wrong life choices and that other people are going to beat them to the opportunities they desire.

Young men are scared of themselves, of their careers, of their future and even of the women they date, especially if those women appear to “have it together” better than they do. These fears and insecurities can manifest themselves in controlling behaviors.

By contrast, many older men feel more secure in who they are, what they’re offering the world and in the decisions they make than younger men. Older men have made their way in the world and won’t feel threatened by your desire to make your own way.

So even though it may sound counterintuitive, you may find yourself surprised to find the older man you have your eye on is far more supportive of you than the seemingly progressive younger men you’re accustomed to.

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