Can Dating an Older Woman Work?

Yes, dating an older woman can work if you find the right person who will respect and inspire you and you discover no relationship deal breakers.

Advantages of dating an older woman

Disadvantages of dating an older woman


Deal breakers

Relationship Potential

What are older women looking for

Advantages of dating an older woman

1. Maturity
One of the most obvious advantages of dating an older woman is her higher level of maturity. Younger women and teenage girls are a lot less mature consequently they tend to be more socially awkward, they tend to have very limited perspectives and experience in the world, and they tend to be both more selfish and idealistic. An older woman has a more accurate understanding of the world and of the compromises that it takes to be successful both in a career and in a relationship.

2. Stability
An older woman tends to have a more stable life than a younger woman. She has already finished her education, she has been pursuing her career for a number of years and she may even have a family. Along with the stability, she tends to have more confidence in herself and her place in the world. Of course, not all older women are stable, some of them are quite erratic but I don’t expect that to be an attractive quality in an older woman. If you want “hot and crazy”, stick with younger women.

3. Realistic
Due to her greater experience, an older woman is much more realistic about what she expects from a man. Young women are filled with fantasies from movies and books and whatnot about finding her Prince Charming dating a hero. She is not just expecting to find a man like that, the media are telling her that she deserves a man like that. And if you don’t measure up, a younger woman will let you know and may even try to force you into that mold whether you like it or not. But an older woman has already been through that phase and come out on the other side. She knows that men are just men and they’re not superheroes or storybook characters. An older woman is more likely to let you be yourself.

4. Inspiring
Older women, especially the ones that are attracted to younger men tend to inspire you and nurture you. Instead of insecurely comparing themselves with you, they can identify your best qualities and bring them out. They are assured in who they are, yet they also know not just who you are but what you can become, and they find ways to bring out the best in you. Because you are not competing with an older woman, you can find a way to complement each other. Your zest for life inspires her and her maturity is a model that challenges you to become your best so that you can become more and more worthy of such a developed woman.

Disadvantages of dating an older woman

5. Her Body
The most obvious of disadvantages of dating an older woman is it her body is older than a younger woman’s body. That means she probably gets sick more often, that means she will get tired more often, that means that she’s going to be getting noticeably older in ways such as increased body fat, wrinkles, menopause, gray hair and all those things that you’ve seen in your mother.

6. Her past relationships
When you date an older woman’ in a way you’re also sharing the date all the other men from her life. That’s because, in ways big and small, she will be mentally comparing you with all the other men she’s had a relationship with including some who are very much more accomplished than you, some much more successful, some much more mature than you. That could make you feel insecure and it could lead you to doubt yourself or it could lead the older woman to complain about you why can’t you be more like her favorite ex.

7. Lack of respect
Hopefully, the older woman will respect you, but by nature, women respect those who are more successful and more accomplished than they are. So it’s going to be an uphill battle to gain and maintain her respect. If a woman, young or old, can’t find something they look up to you for, your relationship is doomed.

Also, Society tends to give you some disrespect for dating an older woman. Many feel that there’s something disreputable about a young man dating an older woman and they will gossip about you, they will cast sidelong glances at you and sometimes they’ll even show this disrespect directly to your face, while other times her family and friends will deliberately exclude you from their activities. Consequently, you have to be a very secure and independent-minded person to face all of that.

8. Culture Conflict
The farther apart you are in ages, the greater the cultural conflict the two of you will experience. Music styles, clothing styles, even the definition of what is cool can change, sometimes quite rapidly. When you want to listen to your favorite music, she may find it quite painful to listen to and you might find her music quite boring.

This is a potential in all relationships but it is going to be a much greater factor due to your age differences and it gets worse when you date somebody who is significantly older than you. Additionally, even though you may be comfortable with each other when you spend time with her friends or her family, you are not going to fit in and likewise, she’s not going to fit in with your friends and your family.


9. Wealth
When I talk about dealmakers, I’m referring to things that you really, really want in a relationship. They meant they may not be common to all older women, but they will seal the deal for you. And the first dealmaker is if the older woman has wealth. In fact, younger women seek to date older men for exactly the same reasons. Let’s face it, if you want to date a woman who’s wealthy, you’re really wasting your time on young women because they’ve paid too much for college and not had time to reap the benefits from it. Or these younger women didn’t go to college at all and their income potential is really small. But an older woman, she’s finished her education, she’s paid for it and she’s working in a career. She may have a nice house and a nice car, she can take vacations in Europe and she has the kind of wealth that attracts you.

10. Connections
Not only do older women have more wealth, they also have more useful connections in the world. The only reason why Harvard is a better University than the University of Iowa is all the connections that Harvard will bring to you. In the same way, an older woman will be more established in life and thus, she’ll have a lot of connections with other successful people that can benefit you as well as association with people who have useful skills that you can take advantage of.

11. Social Status
An older woman is likewise going to have increased social status due to her career, due to her volunteer work, due to her overall longer experience in life. A younger woman is still pretty much a nobody, she still needs to start at the bottom of every organization she works at. The older woman has already paid her dues and now she’s reaping the rewards. Consequently, when you’re with her, you also reap those rewards: you can go with her to the company social activities, you can join her whenever organizations she joins, and go to all the important social events. People may respect you because you are with her.

12. Wisdom
Now the last three dealmakers may seem may make you seem very shallow and selfish but that’s the way some people see things. However, there’s also the advantage that an older woman is going to have more wisdom. By dating this older woman, you can have access to her honest wisdom. She can give you advice on where to invest, and what to wear on formal occasions, on which are the best choices for your career and so on. She can help you be more successful in life by avoiding a lot of stupid mistakes that young men typically make. Likewise, she won’t make the same stupid mistakes young women make either, so you have a double Advantage of wisdom with an older woman.

Deal breakers

12. Career focus
Just as there are deal makers there also deal breakers. There may be some things about an older woman that you just can’t accept and you would do well to stay away. And the most obvious one is to have an intense focus on her career. Since a single older woman doesn’t have a man to rely on, she can pour her life and energy into her work. That might be a turn-off for you because you will not spend as much time with her and you will be a lower priority than her career.

13. Children
An older woman may have children and those children may still be living with her. For a lot of guys, that is a turn-off. Now, if you don’t mind children, this is not a deal-breaker but most young men don’t want to have to deal with some other man’s children. Plus, there’s a concern that she may treat you like just one of her children. Or perhaps you will always be in second place to her children. They are her real treasure and you’re just a trophy.

14. Too close to ex
One of the advantages of an older woman is her experience but that can also be a disadvantage if she is too close to her old boyfriends or old husbands. These men tend to be older than you, they may be a lot more successful than you are, and it can be very intimidating or even humbling to have to interact with her ex’s. And even worse, if she has bad relationships with her ex’s then you will have a lot of drama in your life with people you don’t even care about. As a man, you might end up siding with the ex more than is comfortable for her.

15. Too controlling
Because the older woman has more experience and probably more success in life, she may become a bit controlling over you. She may make you feel like you’re stupid and useless, thus you really just need to be a good little robot and do what she says. Worse, she might actually be right, she might be so much better than you that your best bet is do everything she tells you to do. But that never feels good. Worst of all, this controlling older woman might be completely wrong and she’s still single because she drives other good men away.

Relationship Potential

16. Short-term potential
What kind of relationship potential is there in the short-term with an older woman? Well, you have to ask yourself are you in a hurry to have children because if she wants children, she’s in a race against the clock. That’s going to strongly affect your short-term relationship. In the same way, if she is seeking marriage, she’ll want to get married relatively quickly before she starts looking like your grandma. But if both of you are similar in your desires regarding marriage and children, you can have a very enjoyable time together.

17. Mid-term potential
It’s a bit more difficult in the midterm for your relationship. Now, you have to be concerned with the fact that you’ve got a lot more energy than she does. Are you willing to slow down your social life and your physical relationship as she naturally slows down due to age? It’s often at this point where the young man breaks off the relationship with the older woman. He may seek to focus on women his own age. But, things can still work out if you put in the effort.

18. Long-term potential
There’s no getting around the fact that you won’t have as many years together as with a younger woman other things being equal. But of course other things are never equal, so having a few years with a happy successful older woman could be infinitely more valuable than many years in an unhappy, disastrous relationship with a younger woman. It’s possible you could have a successful relationship with an older woman for many decades although really that doesn’t happen very often.

What are older women looking for in younger men

19. Younger Body
The most obvious thing an older woman is looking for in a younger man is a younger body. He’s stronger, he’s healthier, he doesn’t get sick as often, he’s got a lot of stamina, and he’s a lot better at entertaining an older woman. And he’ll probably look good longer most older men with a dad bod. A younger man who takes care of himself can be fit and trim for decades to come.

20. Interesting life
Older women are attracted to younger men a younger men have interesting lives. An older man perhaps is focused on his career. He’s got a family, he is basically in a habitual pattern that’s not going to change much in the future. But the younger man still has a wide variety of interests, friends and social activities. He has a lot more energy and freedom to pursue various fascinating activities. Many older women find this kind of man very attractive and intriguing.

21. Enthusiasm
A younger man is full of vitality, full of life, energy, and enthusiasm. This is something that attracts older women and they want to absorb some of your enthusiasm and help renew their excitement for life. Successful dates include long moonlit walks on the beach, disco dancing and talking about the latest books. Sometimes she’s had that life before and she wishes to bring it back. Perhaps she didn’t have a chance to really live a full life before because she was too serious about her career. Now you’re giving her a chance to live her life all over again but with more fun.

22. Independent
An older woman is looking for a younger man who can be independent, who won’t always be trying to control her, or always needing her to do things for him. An older woman wants to be able to enjoy her free time with her family, her friends, and her career. Thus, she’d like to have a younger man who has his an friends and his own activities that don’t require her constant attention.

23. Faithful
Well, all women want a man who is faithful. An older woman has probably been through a lot of unsuccessful relationships where the man was not faithful to her. She’s probably decided she’s going to weed out the wheat from the chaff and find a guy who really sticks with her. So an older woman is looking for a guy who can overcome his wandering eye and stay faithful to her especially because she’s not going to get any younger.

24. Growth potential
An older woman knows that a younger man still has room to grow. he’s not a finished masterpiece yet and she finds this interesting and exciting. She wants to be there to help you achieve your best to become more and more of the person she knows you can be. Hopefully she can do this through ennobling you and being a good illustration of success. Then she will thrill at seeing you become a star in your own right.

You may also like...

2 Responses

  1. Staci says:

    Well, this was a fun read. Sure dating older women could work it’s just a matter of if it fits with your current situation. How will your parents feel about it or your peers? You know people have a way of making you feel bad for who you choose to have a relationship with. It’s not always fair. Personally, I have a thing for older men. I just always have and I don’t know why. Maybe it’s the maturity level? They seem more confident.

Leave a Reply

Your email address will not be published. Required fields are marked *