Dating An Older Woman: Benefits, Challenges, and Tips To Make It Work

Dating experience | | , Spiritual Counselor & Writer
Updated On: January 18, 2024
dating an older woman

She is wise. She is independent. She is confident in her skin. As a woman grows and comes into her own, she develops qualities that make her irresistible to many a man. Particularly, those younger than her. For a young man who sees women his own age often held back by self-doubt or societal pressures to be a certain way, her self-assuredness and clarity about what she wants from life can be refreshing. Refreshing enough to make them fall head over heels for her. Even so, the journey from catching feelings to dating an older woman can be daunting.

If that sounds relatable and you’re currently dragging your heels on the matter, spending an inordinate amount of time weighing the benefits of dating an older woman vis-a-vis the challenges, or agonizing over how to impress an older woman so that you can ask her out, or wondering if you can make a relationship work if the woman is older, know that you’re not alone. These doubts and dilemmas are natural. Once you get past them, you can build a truly fascinating connection, where both partners can bring their unique strengths to the relationship.

We’re here to hold your hand through the process of weighing the pros and cons of dating an older woman before acting on your feelings for the one you’ve fallen for. Let’s take a closer look at what it’s like to date an older woman and what you stand to gain in the relationship, along with some tips for dating an older woman.

What Draws Younger Men To Older Women

If you really think about it, it’s not hard to see why a younger man would fall for an older woman. Confident, emotionally stable, mature with worldly experiences, an absolute goddess in bed — what’s not attractive about a woman who’s seen five to ten more summers than you? Plus, her life experiences make her more compassionate, kind, and in all likelihood, more open to embracing life as it comes.

It’s no surprise then that a sizeable section of younger men prefer dating older women. Statistics suggest that 34% of young men aged 22 to 25 years express an interest in older women and prefer to date those 5 to 10 years older than them. So, if you’re in your 20s or 30s, and considering dating an older woman in her 40s, your choice is hardly an aberration or an oddity.

In fact, the many successful age-gap relationships in the public domain are a testament to this fact. Prince Harry and Meghan Markle, Ryan Gosling and Eva Mendes, Gabrielle Union and Dwyane Wade, and Priyanka Chopra and Nick Jonas are just a few examples of couples from public life who have shown us how beautifully this dynamic can work.

Despite the social stigma and the concept of “cougar and toyboy” amplified by popular media, this off-beat relationship dynamic is becoming more popular with time. Researchers suggest that there is a socio-economic reason behind it and the term “cougar” may lose its negative connotation somewhere down the line. An article in the New York Times points out that given the fact that women outlive men by an average of five years, these relationships make perfect sense.

10 Benefits of Dating An Older Woman

Whether you’re a 20-something considering dating an older woman in her 40s or a man in his 30s who has fallen for a woman who is 50, it is natural to have some reservations or doubt how the age gap may affect your dynamic and wonder if you have what it make a relationship work if the woman is older.

However, once you cross that threshold, you realize that the relationship can truly be an enriching experience. But what makes it so? Young men who have had relationships with older women will tell you that the emotional stability they bring to the partnership is, perhaps, one of the biggest perks of dating an older woman. But that’s not all. The benefits of dating an older woman also include:

Related Reading: 10 Must Watch Younger Man Older Woman Relationship Movies

1. Their life experience can be an asset to the relationship

An older woman knows her mind and heart and has seen enough romantic relationships and probably a few heartbreaks to know that it’s best to avoid spending time and energy on trivialities. This life experience is truly seductive and definitely one of the attributes that make older women attractive to younger men.

One of the undeniable facts about older woman-younger man relationships is that she knows herself well and understands the dynamics of couple relationships better. She knows how to navigate a relationship with composure when it veers into rough waters.

2. She knows how to make her partner feel appreciated

When you’re dating an older woman in her 50s or 40s while you’re still in your 30s or 20s, you won’t have to worry about your partner not appreciating you for who you are. She will show affection unabashedly and love sincerely. She has gone through enough to appreciate the little things that are important in a relationship. This appreciation spills over to everything and adds sparkle to every dynamic of the relationship. That’s the biggest perk of dating an older woman.

benefits of dating an older woman
She shows affection unabashedly and loves sincerely

3. Independence is one of the benefits of dating an older woman

If you’re wondering how to date an older woman or what it takes to make a relationship work if the woman is older, you’d be surprised to see how smooth-sailing it can turn out to be. And in great part, it is because an older woman is fiercely independent. She likely has a well-established career and is financially independent.

This, coupled with her emotional maturity, means she can make decisions on her own and doesn’t need to cling to her man or depend solely on him to bail her out. One of the greatest advantages of dating an older woman is that she will be an equal partner in true earnest. This can take a lot of pressure off a young man’s mind — both financially and emotionally.

Related Reading: 15 Ways To Tell If A Married Woman Is In Love With You

4. Older women are more mature

If you’re weighing the pros and cons of dating an older woman, the scales tip in her favor when you know the relationship will not be infested with power struggles or constant drama. She is strong enough to deal with her insecurities and fears and won’t project them on her partner just to escape reality. The age difference can, thus, prove to be an asset in the relationship.

One such example is the power couple, Hugh Jackman and Deborra-Lee Furness. Deborra was already a star when she met the newcomer, Jackman, back in 1995, and as mentioned in many interviews, she instantly felt a soulmate connection. 26 years of marriage later, they are still going steady. That’s the kind of balance and reliability you can expect from an older woman.

5. Great sexual chemistry

Wondering what to expect when dating an older woman? Add amazing love-making sessions to the list. An older woman is sexually uninhibited, understands her body, needs, and desires well, and isn’t self-conscious about communicating these to her partner. All of these can add up to an immensely satisfying sexual relationship and sizzling chemistry between the sheets.

When you date an older woman, you are no longer left grappling with confusion about whether or not you’re showing her a good time in bed. She knows her body and has embraced her sexuality, and that’s why, she doesn’t hesitate to spell out her personal preferences, and may even be more open to experimenting in bed to keep the passion alive. As far as the benefits of dating an older woman go, this one can be hard to top.

Related Reading: Romance Confession: My Affair With an Older Woman

6. The relationship can make you both feel more alive

Younger men feeling drawn to older women isn’t a one-way street. An older woman also enjoys the appreciation and attention she gets from a younger partner. This is likely to make her feel sexier and more alive, which, in turn, livens up the relationship. The passion and excitement both partners bring to each other’s lives can, in fact, serve as the foundation of a strong relationship that can stand the test of time.

7. She is more accepting and forgiving

An older woman’s life experiences make her embrace the concept of acceptance and forgiveness in relationships more easily. She won’t sweat the small stuff, nag you, or fixate on your faults. Her ability to address conflict healthily and maturely is one of the biggest advantages of dating an older woman. Once an issue is resolved, she will be ready to leave it behind. Her experience has taught her that it’s best to let the past bury its dead. So, you won’t have to deal with things said six months or a year ago being brought up in every argument.

8. You can learn a lot from her

One of the benefits of dating an older woman is that as a young guy, you can learn a lot from her. She would push you to get to know yourself better, making you a more confident and content version of yourself. You can share her burdens with her and she will hold your hand and guide you through situations you find yourself lost in. Why is it better to date an older woman, you ask? This itself is a pretty good reason.

Related Reading: 8 Relationship Problems Faced By Couples With Huge Age Difference

9. You can build a mature relationship

Being with an older woman saves you a lot of energy and time in explaining things and feelings. Her intelligence is a byproduct of her age, and she brings it into your relationship dynamic as well. Prepare yourself for profound, intelligent, insightful, meaningful conversations that can captivate you intellectually and make you connect with her on a deeper level. This intellectual intimacy serves as the bedrock of a mature relationship and is unmistakably one of the top pros of dating an older woman.

10. Her confidence makes her sexy

If you’re toying with the idea of dating an older woman, then consider this a really good reason to follow through. A woman who knows what she wants in a relationship is straightforward in asking for it. Her taste and sense of style have evolved over the years to resonate with her personality. That enables her to bring her authentic self into a relationship. Dating an older woman means sharing in on her self-assured sense of confidence, there’s nothing sexier than that.

Relationship Advice for Men

Potential Challenges Of Dating An Older Woman

While there are many benefits of dating an older woman, as with any relationship, you have to be prepared for certain challenges and stumbling blocks along the way as well. Some of the top challenges of dating an older woman include:

  • Different life goals: You are at different stages of life, so, it’s only natural that your goals and priorities will be different. This can lead to clashes and disagreements. To learn how to date an older woman without letting these differences get in the way requires honest and open communication and absolute transparency from both partners right from the start
  • Social disapproval: Is dating an older woman bad for you? It’s not but that’s not how your loved ones and even society at large may view your relationship. Despite the progressive times we live in, social stigma around age-gap relationships remains. You may have to deal with disapproval from family and friends, which can put a strain on your relationship
  • Inability to understand each other’s lifestyles: If the age difference between two partners is significant — say, you’re a 20-something man dating an older woman in her 50s — it can be challenging to understand and accept each other’s lifestyle. This can lead to constant bickering
  • Not wanting/being able to have children: If dating an older woman leads to a serious relationship, the issue of children can become a thorn in the side of the younger partner. An older woman may lean in favor of the childfree lifestyle, may already have kids and not want to go down that road again, or may be unable to get pregnant because of her age. This mismatch, of course, can be hard for a couple to maneuver
  • Lifespan differences: One of the most significant challenges of dating an older woman is the very real risk of outliving one’s partner. This is especially true if the age difference is vast. The fear of losing your partner can impact your day-to-day interactions with them

Related Reading: How To Court A Woman? 21 Ways To Be A True Gentleman

Dating An Older Woman: 11 Tips To Make It Work

Once you understand the benefits and challenges of dating an older woman, take some time to introspect how you feel about the prospect of taking things forward with one you’ve been crushing over. If you’re genuinely interested in taking things forward and avoid the problems faced by couples with a huge age difference typically, you need to learn how to date an older woman without letting the age gap become a defining factor in your relationship. We’re here to help you get it right with these 11 tips for dating an older woman:

1. Focus on her, not her age

One of the most vital tips for dating an older woman is to keep your focus on your partner and not the age gap between you two. You need to show her that you love her for who she is so that she doesn’t feel insecure or unsure about your intentions. Agreed, not every romantic connection develops into a deep, meaningful relationship. Even so, to make sure your relationship is as healthy as it can be for as long as it lasts, it’s imperative to keep your priorities right.

2. Respect her

Now, this piece of advice is not specific to how to date an older woman. And we’re not suggesting that you must respect her because she is older. Respect is one of the cornerstones of any healthy relationship. Here are some ways to respect a woman in a relationship,

  • By being polite 
  • Not crossing the line or saying hurtful things during fights or disagreements 
  • Respecting her boundaries 
  • Respecting her time by not canceling on her or making a habit of being late for dates

It’s the little things that go a long way in helping you really connect with a partner.

Related Reading: Psychology Reveals 7 Traits Of Men Who Like Older Women

3. Don’t pretend to be someone you are not

Yes, her financial stability, her independence, her ability to be her authentic self so unabashedly can be intimidating. However, you mustn’t let it impact your confidence in who you are and make you want to pretend to be someone you’re not. Remember, she’s chosen to be with you. So, bring your authentic self to the relationship so that you can build a deep connection with your partner.

4. Communicate effectively

Again, open and honest communication is one of the pillars on which healthy relationships rest. However, the importance of communicating well and with honesty becomes more pronounced in an age-gap relationship. Given your age difference, your perspectives, viewpoints, and belief systems may clash at some point. When that happens, being able to convey your thoughts and views, and understanding hers, even if you don’t agree with them, can be the key to keeping the relationship afloat.

5. Appreciate her

challenges of dating an older woman
Compliment her and do it often

One of the most vital tips for dating an older woman is to appreciate her (and make sure she knows that you do).

But be genuine about it. Being disingenuous will only make her wary of your intentions.

6. Find common interests

As two partners from different age groups, your idea of fun or unwinding can be different from one another. While you may enjoy clubbing and partying, your older partner may have outgrown these things. That’s why it’s important to find common interests you can bond and connect over. Of course, you can enjoy your respective interests and passions on your own, and that kind of space and independence in a relationship can help nurture the bond, it’s also equally important that you have things to look forward to together to grow as a couple.

Related Reading: 15 Ways A Woman Wants To Be Treated

7. Be confident

If you begin to feel emasculated by the older woman you’re with, the relationship can go south quickly. To not get overshadowed by her, you need to channel your secure, confident side. Show her that you’re a man with a mind of his own, who knows exactly what he wants. And yes, you may not feel this way — secure, confident, and in the know — all the time, and that’s okay. But even if you aren’t feeling confident and self-assured in certain situations, steer clear of self-deprecating, negative self-talk.

8. Don’t be jealous of her success

Chances are that the older woman you’re dating is more successful and at a more stable place in her career than you. Don’t let that become a source of jealousy in your relationship. Instead, treat her experience and success as examples you can learn from. Dating an older woman means you can get some valuable insights into work life and how you can be more organized and focused.

9. Understand her constraints

The key to understanding how to date an older woman is to be mindful of the fact that she had a full life before you walked into it. And she is at that stage in her life where she knows better than to make a relationship the be-all-and-end-all of her existence.

She will continue to honor her commitments and fulfill her responsibilities — both personal and professional — even after she starts dating you. Don’t expect her to give all her time to you and understand the importance of space in the relationship.

 10. Make her a part of your life

Another one of the gold tips for dating an older woman is to not be self-conscious about your relationship with her. Don’t feel embarrassed to introduce her to your friends. Instead, look for opportunities to make her a part of your life, where she has a chance to interact with your inner circle of people. And if you really are embarrassed to be seen with her in public, you need to introspect why you’re with her in the first place.

Related Reading: Effort In A Relationship: What It Means And 12 Ways To Show It

11. Make an effort in the relationship

Don’t slack on the charm that made her fall for you. Be exciting and appealing.

  • Think of some fun date ideas
  • Take her out to dinner
  • Plan a simple picnic day to spend the day with her
  • Look for new activities you can connect over

Don’t let the romance die. No matter their age, women are women, and they will always appreciate romantic gestures that make them feel special.

Key Pointers

  • Confident, emotionally stable, mature with worldly experiences, older women can be immensely attractive
  • Her life experiences, independence, ability to not sweat the small stuff and appreciate the little things in life, along with a fiery sexual relationship, are the biggest benefits of dating an older woman
  • However, such a relationship isn’t without its challenges. You may have to deal with social stigma, differences of opinion, and her health concerns — all of which can negatively impact the relationship
  • Communication, respect, appreciation, and making a consistent effort in the relationship are some ways you can overcome those challenges and build a wholesome, fulfilling relationship with an older woman

When it comes to the pros and cons of dating an older woman, the advantages far outweigh the disadvantages. How well you can make the relationship work really depends on how well you maneuver through the challenges and make an effort to nurture your connection. Of course, don’t forget to enjoy every moment you share with her!


1. Why do guys want to date older women?

Older women are emotionally more stable and are capable of sustaining a mature relationship. There are no unreal expectations or unnecessary criticism. The confidence factor in an older woman about herself is good enough to madly attract younger guys.

2. What are the disadvantages of dating an older woman?

The major disadvantage of dating an older woman is social stigma. You may have to face many negative comments and judgments from your family and friends for getting into such an unconventional relationship frame. Being in two different stages in life, your goals must be different. Plus, her baggage from the previous relationships might fall as a burden on yours.

3. Do relationships work if the woman is older?

Yes, there are several examples of younger men older women relationships in the public domain that suggest that these partnerships can work wonderfully. If both partners are sure that this is exactly what they want and they are ready to go against all odds, it will turn into a relationship just like any other.

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Readers Comments On “Dating An Older Woman: Benefits, Challenges, and Tips To Make It Work”

  1. Jonathan Dahlin

    The fifth one – really? Always? I always thought there was more variation that there’d be some older women that suck between the sheets and there’d be some younger women are great between the sheets.
    I think the sweet spot is that the woman should be three to six years older. Never marry a woman old enough to be your mother.
    Not all older women are the same, and not all younger women are the same. Is there not so much variation?

  2. May-December Romance can be quite something if everything falls into place. And well, as a woman i can definitely say that with passing time, a woman who is constantly working on herself only gets better. So definitely dating an amazing , self-assured woman who is older than you can be nourishing in more than one ways.

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