Have you ever been drawn to a woman much older than you, and then found yourself wondering, why does she seem like an elixir of beauty and grace? 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. It’s no wonder, then, that dating an older woman is such an exciting proposition. 

For a young man who sees women his own age often held back by self-doubt or societal pressures, the self-assuredness and clarity about her goals that an older woman showcases make her tremendously attractive. 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 who have shown us how beautifully this dynamic can work. 

But are you wondering if it’s okay to ask her out? Are you scared or intimidated by her presence? You can build a truly fascinating connection, once you’ve moved past these doubts and insecurities. To help you do that, let’s take a closer look at what it’s like to date an older woman and, along with some older woman younger man relationship advice.

Why Do Young Men Like Older Women?

So, why would a younger man fall for an older woman? Well, simply because she’s confident, emotionally stable, mature with worldly experiences, and an absolute goddess in bed! Plus, her life experiences may have made her more compassionate, kind, and welcoming. Statistics suggest that 34% of young men aged 22 to 25 are interested 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 are considering dating an older woman in her 40s, you are not alone. 

Related Reading: 10 Year Age Difference In Marriage

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. In fact, 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. We believe you now have the answer to, why do young men like older women. Let’s explore the pros and cons of such relationships, along with some tips on how to make them work. 

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 doubts regarding the age gap. However, a lot of 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 a woman older than you. 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. Her life experience 

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. Her ability to make her partner feel appreciated

When you’re dating mature women in their 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.

For instance, my friend, Cathy, a single mother in her 40s, has been blissfully happy in her relationship with Jonathan, a 32-year-old food vlogger she met on Instagram. They hit it off instantly and have been dating ever since. Jonathan is now also a father figure to Cathy’s 10-year-old son. This has been possible because Cathy had realistic expectations from her relationship initially and loved and appreciated every little effort Jonathan put into the relationship.

3. Her independence 

If you’re wondering how to date a woman older than you or what it takes to make a relationship work if the woman you fancy is older, you’d be surprised to see how smooth it can turn out to be. And in most cases, it is because an older woman is fiercely independent. She likely has a well-established career and is financially independent. This is coupled with the fact that:

• She can make decisions on her own 
• She doesn’t need to cling to her man or depend on him
• She is an equal partner 

This can take a lot of pressure off a young man’s mind — both financially and emotionally. That undoubtedly is one of the biggest benefits of dating an older woman.

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

4. Her maturity

If you’re weighing the pros and cons of older women with younger men, the scales tip in her favor when you know the relationship will not be plagued by 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.

5. Her sexual knowledge

Wondering what you should be expecting when dating a woman older than you? Add amazing love-making sessions to the list. And here’s why:

• An older woman is sexually uninhibited and understands her body, needs, and desires well
• She isn’t self-conscious about communicating her sexual needs to her partner 
• You are no longer left grappling with confusion about whether or not she is having a good time in bed
• She is more open to experimenting in bed with a younger man and may try various sexual positions and kinks 

Here’s how a Reddit user explains the same: “Older women are just way more aggressive and go after what they want. They don’t care about being seen as “easy” or a “slut” like their younger counterparts.” Now, if that doesn’t count as one of the top benefits of dating an older woman, what would?

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

6. The fun factor

Younger men feeling drawn to older women isn’t a one-way street. An older woman too enjoys the appreciation and attention she gets from a younger partner. This makes 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. In fact, older women dating younger men don’t seem to care about social norms and other people’s opinions, and this allows them to enjoy their relationship to the fullest.

7. Her forgiving nature

An older woman’s life experiences make her embrace the concept of acceptance and forgiveness in relationships more easily. So, this is what you can expect:

• 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

8. Her worldly-wise ways

One of the benefits of dating an older woman is that as a young man, 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. She will hold your hand and guide you through situations you find yourself lost in. Here are the probable reasons:

• She has climbed up the career ladder and knows what it takes to succeed
• She is better-traveled than you and has met many people from across the country or the globe, and can thus read human emotions better
• She has dated many men in the past or has handled a marriage or multiple long-term relationships, which makes her more experienced in dealing with relationship issues

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

9. Deep conversations

An older woman’s intelligence is a byproduct of her age, and she brings that into your relationship dynamic as well. So, prepare yourself for profound, intelligent, insightful, and 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 serious relationship and is unmistakably one of the biggest advantages of dating mature women.

10. Her confidence 

Older women with younger men pairings work because these women know how to navigate relationships confidently. A mature woman who knows what she wants in a relationship and is straightforward in asking for it. So, expect the following:

• A sense of style that has evolved over the years to resonate with her personality
• Her confident demeanor that reflects in the way she walks and talks
• Her confidence in the way she asks for what she wants: be it a fling or an emotional connection

Dating an older woman means getting a taste of her self-assured sense of confidence, and there’s nothing sexier than that.

Potential Challenges Of Dating An Older Woman

While there are many benefits of dating attractive older women, 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 older women include: 

1. Different life goals

This is one of the cons of a mature woman dating younger man. Don’t forget that 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 a woman older than you without letting these differences get in the way requires honest and open communication and absolute transparency from both partners right from the start. 

Related Reading: I Had A Crush On An Older Woman And It Changed Me

2. Social disapproval

Age-gap relationships aren’t always approved of. Your loved ones may cast aspersions on your relationship and you may even face judgment from society at large. This may leave you wondering, is dating older women bad? It’s not, you have to brace for the fact that a mature woman dating younger man can have its fair share of snubs from society.

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 strain your relationship. A Reddit user in a similar situation says, “I’m34f, he’s 21m. He probably has to hide dating me from his family… the way I see it though when you guys are in love …. Like love love. That’s when it won’t be an issue because you won’t care about what anyone thinks at that point.”

3. 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. For instance, my cousin, Debbie, a 44-year-old photographer, was once in a relationship with a 25-year-old art intern, Jay. Jay would often get upset when Debbie would go on long trips for her shoots, and this eventually led to their breakup.

Related Reading: When the young bachelor met the lonely housewife

4. Not wanting/being able to have children

One of the challenges of dating an older woman is the issue of having children. While the younger man may wish to have kids, the older woman may not. This is why:

• An older woman may prefer a childfree lifestyle
• She may already have kids and not want to go down that road again
• She may be unable to get pregnant because of her age 

This mismatch can be hard for a couple to maneuver.

5. Death and ailments

One of the most significant challenges of dating older women is the risk of outliving one’s partner. This is especially true if the age difference is vast. The fear of losing the older partner due to death or of a healthy lifestyle being affected by the older woman’s illnesses can lead to serious problems in the relationship.

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 older women, take some time to introspect how you feel about the prospect of taking things forward with the one you’ve been crushing over. If you’re genuinely interested in a relationship with her and want to avoid the problems faced by couples with a huge age difference, you need to learn how to navigate this connection without letting the age gap become an overshadowing factor. 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. We agree that 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. In fact, respect is one of the cornerstones of any healthy relationship. Here are some ways to respect a woman in a relationship:

• By being polite 
• By not crossing the line or saying hurtful things during fights or disagreements 
• By respecting her boundaries 
• By respecting her time 
• By being true to your intentions

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, and 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. One of my friends, Roy, a 29-year-old banker, was so determined to win over his older crush, 48-year-old travel vlogger Rita, that he pretended to love travel. He even promised to go on trips with her to impress her, but he could hardly make time for her, let alone travel with her.

4. Communicate effectively

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

One of the most vital tips for dating an older woman is to appreciate her (and make sure she knows that you do). This is how you can go about it:

• Pay her compliments 
• Express gratitude. Thank her for little things like cooking your favorite dish
• Let her know you value her presence in your life

But keep in mind that being disingenuous will only make her wary of your intentions.

Related Reading: 101 Beautiful Compliments For Women To Melt Their Hearts

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. 

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. Even if you aren’t feeling confident and self-assured in certain situations, steer clear of self-deprecating, negative self-talk.

Related Reading: 15 Ways A Woman Wants To Be Treated

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. Give her enough space

Here’s one good older woman younger man relationship advice: nurture space. 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 golden tip on how to impress 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 

Don’t slack on the charm that made her fall for you. Likewise, don’t take her for granted. Be exciting and appealing. Here are some tips:

• Think of some fun date ideas that resonate with both of you
• Take her out to a romantic candle-lit dinner at a restaurant that plays music from her era
• Plan a simple picnic day to spend the day with her
• Look for new activities you can connect over such as fitness classes 

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

Final Thoughts

When it comes to the advantages and disadvantages of dating a woman older than you, 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. But while doing so, don’t forget to enjoy every moment you share with her! 

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