Dating An Older Woman (Advantages/ Disadvantages)

Older women are more secure in themselves and know what they want in life. They also have greater life experience. Although you are happy, people may judge the relationship, but this should not deter you. You do need to be as emotionally mature as her and understand that she may have baggage.

In days gone by, the thought of a younger man dating an older woman was not exactly frowned upon, but I would not go so far as to say that it was encouraged. However, if you are like me, you have considered the option of going after someone a few years your senior and are now wondering what the potential pros and cons of doing so are.

This is just the tip of the iceberg; I could talk endlessly about the various points one needs to consider before entering or continuing a relationship with an older woman. So I have given you a glimpse into what to expect of your relationship, but now let’s get into the nitty-gritty of romantic relations with an older woman.

Younger man who is dating an older woman is holding a rose behind his back on the beach waiting for his date

The Advantages Of Dating An Older Woman

You may be considering the possibility of entering into a relationship with an older woman. Or perhaps you happen to have your eyes on a lady and have discovered that you are in different stages of life.

Older Women Are Confident In Themselves And Know What They Want

Not to bash younger women, but they often do not know exactly what they are looking for in a relationship. They might still be starting out in their careers and aren’t willing to fully commit to a relationship, or they are all about the relationship but haven’t got the rest of their lives in order.

This is different for older women, as they typically, not always (we can’t completely generalize) know what they want out of life. They have tried and tested different things and are surer of what they want from a relationship. This does not mean that they will all want the same thing though, some may be looking for marriage material, while others are merely after a boy toy.

Regardless of this, though, she will likely be upfront with you and won’t beat around the bush about things. She will also unlikely be cryptic about her expectations, as younger women usually tend to be.

Being Older Doesn’t Mean She’s Less Fun

You may be after a woman in her forties or even fifties, and you will discover that just because she’s older does not mean that she does not have a funny bone. Older women still know how to have fun, and they can be silly when they want. Just because they are more mature does not mean the fun factor goes out the door.

You may find yourself with a woman who has already been through a marriage and had kids and is now in a space where she wants to rediscover her youthful exuberance. All the demand for having to be responsible as an adult can often lead to a woman wanting to let her hair down and just have fun with you. 

However, with this being said, she is also more mature and possibly more intelligent than her younger counterparts, which means that she is a more rational and logical person when dealing with potential issues.

She Is More Independent

This is an attractive factor about an older woman; she is less likely to be dependant and “clingy”. She is likely established financially, which will make her more confident in herself and, ultimately, the relationship.

She will be more likely to make her own decisions, and this is where you’ll have less work, as opposed to younger women who sometimes look to their man for guidance. Ultimately this will be great for you as she will be able to survive on her own when you are not around, and as long as you hold up your end of things, life should be smooth sailings.

So you won’t have to worry about providing for her as she will have that covered. This will take off a lot of the pressure which you will likely endure were you to date a younger woman. You will be taxed less financially and emotionally at the end of the day with your older woman.

She Has More Experience In The Bedroom

An older woman, in most cases, is going to have the know-how when it comes to getting between the sheets. She knows what she likes and what pleases her and won’t be shy to tell you what she wants.

With her experience, things will get truly steamy in bed, and she will likely be quite uninhibited. She has probably accepted her body for what it is and won’t be shy and precious about you seeing the odd stretch mark.

She is also more likely willing to experiment as she may be tired of the same old thing, so she will want to spice things up now and then. She will also be able to teach you a thing or two, which you may have previously been unbeknownst to. So rest assured the lovemaking is surely going to be passionate and unbridled.

You also won’t have to worry about whether you are giving her a good time, as with younger women; instead, she will tell you when you are doing something the wrong or right way.

The Disadvantages Of Dating An Older Woman

Okay, so I have spelled out the great things about dating an older woman, but unfortunately, there is going to be a downside with all things. This is also the case for our current topic, so let us explore what may deter you from dating someone older.

Her Biological Clock Is Ticking

One thing to consider is that although she may look fantastic now, this is going to change in a certain period of time. This is also the case with dating younger women, but that clock is not as far ahead.

Another thing to bear in mind is whether or not she is looking to have children. You may just be after having fun with someone who has more experience than yourself, but she may be looking for someone to be her baby daddy.

People May Judge You

This is a case where honestly, it is your business and no one else’s in terms of who you date. However, it must be said that you are likely going to get comments from people, and these are probably going to be those closest to you.

Your friends and family may well either cheer you on, but in many cases, they will have snide comments and remarks. So just as long as you are confident in yourself and are happy in the relationship, just be aware that you may need to shrug off the naysayers.

This flack may not even depend on the actual age gap between the two of you, but more on your age appearance. If you look more-or-less the same age, people are less likely to pass comments.

She May Have Baggage

This could come in many ways and forms. You need to realize that she has lived a longer life than you, and hence she may be carrying around ghosts from her past, or she has responsibilities such as children. She may also have been hurt more times in her life and thus not be as willing to be vulnerable with you emotionally as a younger woman would.

Her job is also likely more important to her than a younger woman, and she may often not prioritize you over it. Her career is a big portion of her life, and although she will want to spend time with you and have fun, she understands the concept of being a responsible adult.

You May Not Be As Emotionally Mature

Although dating an older woman has great appeal to many younger men, you have to be aware that your emotional and general maturity (this does not mean you can’t have fun and be silly, though) needs to match hers.

If she is after something serious, she will want you to be a mature adult about things and to be certain about her. You also need to be good at communicating. And if these are things that you struggle with, you might be better off dating someone your age or younger.

Related Reading: How To Date Without Your Parents Knowing


So there we have it, the advantages and disadvantages of dating an older woman. The decision to initiate a relationship will need some careful thought, and you will need to weigh the pros and cons for yourself. Once you have done considering the various factors, be sure that you are honest about whether it is for you.

There are certainly great advantages, which unfortunately come with disadvantages, and when it comes down to it, each case is different. So consider yourself and the woman and make a decision that will be beneficial to you both. Be aware of what you are both looking for from the offset to avoid any heartbreak or confusion later on.

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