Dating An Older Woman

Dating an Old Woman: Pros, Cons & Helpful Relationship Advice

by John Santana

If you are a younger man looking to date an older woman, this guide will be helpful. It’s not uncommon for a man of your age to date someone who is significantly older than them. You could be in your 20s and intend on dating a woman in her 30s or 40s.

You may have no active intention of dating an older woman. But you met one and the two of you seem to hit it off. It seems like the two of you might be considering a romantic relationship.

Nevertheless, this guide will provide you with tips and strategies that apply to dating an older woman. Let’s get started.

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What Are The Benefits Of Dating An Older Woman?

There are plenty of benefits for a younger man to date an older woman.

Here’s what you might enjoy should a relationship happen:

Older Women Know What They Want

Older women are the kind of people that know what they want. Unlike younger women, their older counterparts have no room to play games. They’ll make that known through communication.

This may be someone you’re happy with. She’s direct, to the point, and knows exactly what she’s looking for. If you can deliver the goods, then the chance of a relationship between you is possible.

Over time, older women have spent time learning about themselves. At that time, they were able to know what their needs and wants were in life. This includes what they look for in a relationship.

She may be surprised that a younger man like yourself has his stuff together. You may be stable in many areas of your life and she’s looking for stability herself.

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She Has The Experience (and wants to share with you)

Romantic man kissing Girlfriend's hand

An older woman will be more experienced in terms of relationships, sex, and life overall. If you are younger, you can benefit from learning all of this from her. You may be in one stage of your life and she might be happy to be a key player in bettering your life.

Don’t mistake this as her being your babysitter or mother. You need to put in the work in regard to your own life experiences. It’s still important to be self-sufficient.

She may have some experience in some of life’s challenges. You may be dealing with the same. She’ll be there to support you, provide you with advice, and do whatever she can to help you out.

She Has Better Control Over Her Emotions

An older woman has been through challenges in her life. She also learned from them. This also gave her the opportunity to learn how to control her emotions.

Most (not all) younger women have little ability in regulating their emotions. That’s because they haven’t dealt with some of the life challenges older women have experienced. You, as a man, want someone who is emotionally stable for a romantic partner.

Your best chances will lie in someone who is older than you. Yes, some younger women can handle their emotions. But they may be hard to come by these days.

She Is An Independent Woman

An older woman is independent and secure with herself. Which means she is self-sufficient in many areas of her life. As mentioned earlier, she expects her partner to be the same.

If that’s you, that’s a huge plus. This means less pressure on her to ‘babysit’ you (so to speak). It’s also important to consider the life stages the two of you are at.

You might have the desire to start a family of your own. She might have already done so with a former partner or spouse. If she has no children of her own, she might have her reasons.

Some older women without children may want to start a family. Others may not want to. If her wants and needs are not a match with yours, it’s obvious a relationship won’t work out.

Marriage is another topic we should bring up. Does she want to get married again? Or does she just want a lifelong partnership without the ‘paperwork’?

Again, it’s all about the needs and wants you two have. If the two of you want to get married in the future, that’s a plus. If the both of you just want to stay together and not worry about matrimony in the slightest, that’s fine too.

She Might Want a No-Strings-Attached Relationship

If you are someone who may not care so much about commitment, this is a plus. Especially if the woman was divorced prior to the relationship. She may not want marriage and wants to have a bit of fun.

A no-strings-attached relationship will be a problem-free, no-pressure kind of thing between you two. If you are someone that wants commitment in the future, it’s clear that a relationship with a non-committed woman won’t be in the cards.

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The Challenges Of Dating An Older Woman


Yes, dating an older woman has its challenges. Not everything will be perfect, which is why you need to know what the common downsides may be.

Let’s take a look at what they are:

You May Face Disapproval

There’s an ongoing stigma around age-gap relationships. For this reason, there may be friends or even members of yours (or the woman’s family) that won’t approve of the relationship. Granted, some may come around and accept it once they realize how happy you two are. But don’t let this stigma discourage the both of you in the slightest.

She May Not Want To Have (more) Children

As mentioned earlier, an older woman may not want to have children. Either she’s already raised her own or may choose to be childless by choice. Either way, there’s nothing wrong with her decision in terms of starting a family.

This is a crucial subject that can make or break a relationship. After 40, her chances of getting pregnant are lesser compared to a younger woman. Menopause starts between 45 and 50 years of age. So age will be important here.

If you’re 22 and she’s 35, the chance of starting a family is greater. If you’re 25 and she’s 50, starting a family may be done via adoption rather than the natural process. Again, it comes down to the intents and desires of starting a family between you two.

Social References Will Differ

You may be from one generation and she might be from another. Which means there may be a misunderstanding of cultural references. This can be an issue for some relationships.

However, if you’re both comfortable with it, discuss the cultural references between the two generations. You may learn some things from each other and be fascinated. Besides, isn’t it exciting when you and your older partner learn more about each other?

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Different Life Stages

We’ve already brought this point up a few times already. But it bears mentioning again. You may be at one stage of your life and the woman you intend to date is in another.

She may be in the middle of working on a career that she built. She may also be continuing her responsibilities as a parent. You may be wrapping up your undergraduate studies and beginning a new chapter of your life.

So there may be some issues that can happen because of the different life stages you’re both at. Plus, there are obligations and responsibilities that come at every stage. Understand that she has her own things to deal with, as do you.

Have a mutual understanding and acknowledgment of this and the relationship may continue to thrive.

Potential Power Differences

The relationship may have its share of power struggles. This can be due to differences in career, life experiences, and income (among other factors). An older woman will have the advantage in most of these areas.

5 Tips To Follow When Dating Older Women

Beautiful lady using mobile phone

Now that you know the benefits and challenges, you may have entered a relationship with an older woman. If that is the case, you’ll want to follow these tips below to make it last:

1. Be Self-Sufficient

Another point that needs to be brought up again is self-sufficiency. An older woman would want a younger man to be independent. She may be raising her own children.

She doesn’t want to ‘raise’ you as if you were her own child. The differences in life stage and the age-gap are fine. But it’s important that you both are self-sufficient and be able to meet each other’s needs when necessary.

2. Have Your Own Life Outside Of The Relationship

The two of you have a life that you both can build together. However, you’ll want to build one outside of it. In other words, you have your own priorities to deal with.

You can do the things that you enjoy, such as the hobbies you love or focus on interests you are passionate about. If you have your own career, do your best to build it into something stable.

Remember, this doesn’t mean neglecting your relationship. You need to maintain it on your end on a regular basis. Not having a life outside of the relationship can be seen as needy and you’ll be viewed as someone who isn’t ‘self-sufficient.’

3. Accept The Fact About Getting Older

We’re all getting older. Unless you’re Benjamin Button, there is no aging in reverse. That’s something that we’re going to accept.

There will also be noticeable changes as well. You can consider cosmetic treatments all you want. But those are temporary things.

An older woman may feel the same way. It’s important to let the chips fall where they may. Don’t worry about aging and encourage the woman you’re dating not to feel bad about it.

4. Communicate Regularly

Communication is one of the biggest building blocks of any relationship. So it’s important that you and the woman you’re dating do this regularly. This can also include talking about difficult topics such as commitment and raising a family.

You two may have some differences on things. It would be wise to discuss the differences and try to get their perspective on what makes them think a certain way. Don’t try to demean and force her to change her mind.

5. Make Your Opinions Clear On Family And Kids

If you don’t mind dating a woman with kids, then this can be easier to make your opinion about it known. Dating an older woman means there’s a chance that she will have kids from her previous relationships or marriages.

If that is something that you cannot accept, then dating an older woman may not be right for you. An older woman without kids may exist. However, they may be much harder to find.

Raising a family alongside your older partner will have its share of challenges. Yet, if you have solid emotional intelligence and the understanding that it’s a team sport, it will make it slightly more bearable.

Her kids may have school, outside obligations such as sports, club meetings, or something else they are involved in. This may be a daunting challenge if you’re a younger man who has never had kids. However, you and your partner can work things out and do your best to raise children so they grow up and live by yours and their mother’s teachings and examples.

Who knows? You may be better at the parenting thing than you previously assumed.

Final Thoughts

Dating an older woman comes with its share of challenges. Yet, there are a handful of benefits that you’ll enjoy. If you and an older woman are attracted to one another, there’s a chance that a relationship will blossom.

Whether it’s something that’s long-term or turns into a marriage, one thing’s for sure. You and your partner deserve happiness. Keep in mind that there are elements to a relationship that need to be fulfilled.

This includes regular communication, giving each other space, and building a long-lasting life with each other. If there’s an older woman that is interested in you, why not make your move now instead of never?

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John Santana

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