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How to Make Dating an Older Woman Much Easier - 44 Experts Share Their Best Tips

Learn about dating older women like this

If you want to know how to date older women, you need to take a different approach than you have in the past. Dating an older woman isn’t the easiest thing to do, especially if you’ve only dated younger women or women your age. However, with the crucial tips we’re about to share, you can increase your chances of landing an older girlfriend.

We’ve gathered some insight on how to date older women from some dating experts. These experts know the ins and outs of dating, and they’re particularly keen on helping men date older women with ease.

These tips will come in handy for any man dating an older woman (don't forget to check out our favorite ways to meet single older women). Take a look and then get out there and put it to use!

How to Date Older Women

If you’re just getting curious about how to date older women, here are some useful tips you should keep in mind. These will increase your chances of getting a girlfriend who’s much more mature than you.

Her values are not the same as a younger woman

There is a clear difference between what older women and younger women value.

Yes, there are some aspects of a man that they find universally attractive. So it will always help you to be well-presented, funny, confident and good in bed.

However, older women aren’t going to be as bothered about superficial traits like your fashion sense, your height or whether you’re friends with the popular guys.

Instead, they care more about what’s on the inside. Are you intelligent? Are you passionate? Are you wise beyond your years? Do you have your life together?

These are values that will really stand out when you date older women.

“The secret to a successful relationship with an older woman is the same with a younger woman. Be gentle, be kind, be fun and be loving.

When dating an older woman, know that her values are not the same as a younger woman. While sex is important, it won't be her priority. The solution in this scenario is to invest more time in romance and intimacy, which will get her in the mood for sex more often.”

Cheyenne Bostock - AskCheyb.com

Cheyenne Bostock profile

Be assertive

Older women don’t have as much time for guys who aren’t sure of themselves. They’re well aware that they don’t have time to waste! So, if you’re aren’t sure if you want to be together, they could easily decide to drop you immediately. 

If you aren’t sure what you want from your life in general, that’s going to be a much bigger turn-off for older women. Younger girls could be more forgiving of these traits because they tend to be pretty clueless about these things too. 

When you’re assertive about what you want and who you want, that’s going to impress an older woman.

“Older women are interested in younger men, not younger boys.  They want a man who is mature and confident.  They know if a man is being dishonest or playing games. They don't want to waste their time, so they won't hesitate to move on sooner rather than later.”

Lucia - HowToCatchACougar.net

Lucia profile

Teach her new things

She may be the one with more life experience, but that doesn’t mean she doesn’t want a man who can’t teach her new things. Most likely, she has a thirst for knowledge! 

For her, a big part of the appeal of dating a younger guy is that she can keep up-to-date with current trends and what’s going on with the younger generations.

So, don’t hesitate to bring an older woman into your world. Tell her about your day. Show her your passions. Ask her opinion on the hot new band. This will make her much more excited to be around you - and help her to feel more youthful.

If you want to get older women excited to keep seeing you, this is how to do it.        

“Remember that while an older woman has had many unique life experiences that she can share with you, she also may be a little attached to the way she does things.

Encourage her to do new things with you while also acknowledging how much you appreciate the ways she's opening up your world.”

Damona Hoffman - DamonaHoffman.com

Damona Hoffman profile

Authenticity is key 

When you’re in a significant age-gap relationship, you might feel the urge to alter your personality to what you think your partner will prefer.

The thing is: an older woman will see right through this. Women are socially-savvy as it is. A mature woman has been around the block enough times to smell this bullcrap a mile away. 

Inauthenticity is a huge turn-off because it signals you’re not confident in who you really are. 

It’s also wasting this woman’s time because she’s going to discover the real you eventually. As cliche as it sounds, it’s better to BE YOURSELF. 

Most likely, she’s chosen to date a younger guy because she appreciates the positive qualities of younger men. So, go ahead and show her these qualities.   

“You know you’ve lived a rich and rewarding life and you can’t wait to tell her just how rich and rewarding. Plus, you know exactly what you want and don’t want in a woman. But guess what? So does she. Older women dating younger men have lived a full life too, and she also knows what she wants.

So cut the crap. Be authentic. That means be who you really are, good qualities and warts. She’s got to love the real you, not some idealized version, because: Guess which person she’s going to be living with? A big bonus: when you’re authentic, there’s a good chance she’ll be, too. You’ll both find out if you’re each keepers or if it’s time to look elsewhere. That’s how it should be because that’s what real men and real women do.”

Dennis Work - Guyvorce.com

Dennis Work profile

Issues With Dating an Older Woman

When you have an older girlfriend, you’re not exempt from some common relationship issues. However, some relationship hangups are unique to younger men dating older women. Here’s how to get through them.

An older woman might not be down with modern technology

There are plenty of tech-savvy older women out there, but there’s no guarantee that your partner is one of them. It’s worth bearing this in mind when you’re apart from her and trying to communicate.

Does she understand and appreciate your Spongebob Squarepants memes? Will she be impressed by your fire Snapchat stories? Does she even know what a fire Snapchat story is? 

Most older women prefer to talk on the phone rather than sending selfies or mindlessly texting throughout the day. So, don’t be afraid to dial her phone number and talk like they used to do back in her day.    

Think ‘old school’ in terms of your communication. In other words, instead of texting her, pick up the phone, and call her!

“Older women will appreciate a man who doesn't initiate important discussions in one hundred sixty characters or less. Put down your devices, pay attention to her, and have some good old-fashioned conversation--in person.”

Rachel Russo - RachelRusso.com

Rachel Russo profile

She can become insecure about younger women 

No matter how confident she appears, no matter how much affection you give her, there will always be a tiny fear lurking in this woman’s head (if she really likes you). This is the fear that you’re going to trade her in for a younger model. 

There’s really not too much you can do to help eliminate this fear - but you shouldn’t do anything to FEED it.

That means: don’t get caught staring at the waitress’ ass after she serves your cocktails. Don’t be ogling over female celebrities in the magazines. Don’t be too touchy-feely with your female friends.

Honestly, these rules will serve you well in any relationship, but it could really play on an older woman’s insecurities - and not in a way that makes her want you more. 

If she senses that you really want to be dating younger women, she might just be strong enough to leave you to it.  

“Don’t make a big deal of the age difference. There is no need to focus your attention on it. She is well aware of it and if she wasn’t comfortable with it she would not have agreed to go out with you in the first place.

“Women who date younger men have much more competition and they are well aware of that as well. Whatever you do, don’t get caught checking out the cute younger hostess on your date with an older woman.

“Older women can be much more decisive and unforgiving at times. Give her the attention she deserves, pursue her like she is the only woman in the world and you will be rewarded in more ways than you can ever imagine.”

Denise Levy - MissMatchMakerLive.com

Denise Levy profile

Playing games is a great way to piss off an older woman

You may have got used to playing silly mind games when you’re courting younger women. Maybe you think it’s important to “make her chase” or “punish bad behavior.” Perhaps, you see it as part of the process of winning a woman over. Certain brands of sleazy dating coaches will tell you it is!

But, you’re not trying to attract insecure party girls here! You’re going for an intelligent mature woman. As we’ve explored, older women can sense when a man is being fake almost immediately and inauthenticity pisses them off. So, you’re best off leaving the mind games to all the pick-up artists out there. 

It’s important for you to earn an older woman’s trust by being genuine with her. Playing games is the opposite of that - and older women have no patience for this type of behavior.     

“Don't play games. Most older women (the type you probably want to date anyways) can see through the bullshit, and they won't put up with it. They know what they want, and they don't want to waste time playing games anymore.

In short, playing games is a great way to piss an older woman off and cause her to lose interest in you.”

Kari - AttractGetWomen.com

Kari profile

Immaturity can be a real turn-off

In a relationship with a younger woman, you can forgive each other’s immaturity. In fact, you might even both find it somewhat cute.

It’s different when you’re dating an older woman. An act of immaturity might trigger her fears that dating a young man isn’t right for her. You can bet the first thing her friends asked her when hearing your age was: “isn’t he too immature for you?”

That’s not to say you can’t have a laugh together. In fact, you should. Authenticity is key, after all.

But, if you’re acting immature during a disagreement or you fail to do a basic job for her because of an immature reason, that could really ring the alarm bells in her head.      

“Don't act like a little boy. She is a mature woman who has her shit together. Maybe she even has children. The last thing she wants is to date a little boy who appears more immature than her kids or the kids of her friends.

“Dress appropriately when you approach an older woman. Speak like a mature man and avoid "youth slang" just to appear cool. It won't work. Yes, she wants to date an adventurous young man who has more energy than most men in her age range, but she doesn't want to date a child.”

Sebastian Harris - GlobalSeducer.com

Sebastian Harris profile

Older Woman Younger Man Relationship Advice

Need more advice when it comes to dating anolder women? Here are a few more things to keep in mind after you’ve landed yourself an older girlfriend.

Genuinely make her feel like she's still got it

It’s no secret that a woman’s beauty fades as she ages. She knows she’s not the same bombshell she was when she was 21. But that doesn’t mean you should hold back from showing her you’re physically attracted to her. 

A woman is never too old to enjoy a playful butt squeeze or some dirty talk whispered into her ear from her horny partner. If she’s dating a younger man, she definitely still wants these sorts of lustful gestures from her man. These are the sort of moves that make her feel young again. 

More importantly, this is what makes her feel sexy. Not beautiful or elegant. SEXY. An older woman dating a younger man wants to be made to feel this way, even if nature has evidently taken its course on her body. So, if you find her sexy, don’t hesitate to let her know about it!  

“As an older woman dating younger men ages into her 30s, 40s and 50s, her physical appearance will no longer look the same as she did when she was in her 20s. This may begin to eat away at the confidence that she has in her sex appeal.

If a man is genuinely attracted to an older woman, he must ensure that he doesn't hold back from showing his sexual attraction for her. Be confident and sincere when you say to her, "Wow, you look sexy today" rather than hiding your attraction and saying, "Oh, you look nice today."

Dan Bacon - TheModernMan.com

Dan Bacon profile

Validate her because of who she is

Your relationship is more than an older woman younger man romance. At least that’s what she wants, anyway. She doesn’t want to feel like you’re only with her because she’s older. She definitely doesn’t want to sense that you’d date any older woman who would have you. 

So, don’t focus too much on the age gap, even if you’re talking about it in a positive way. Focus on her personality, her looks, who she is and how she makes you feel. These are the things that make a relationship last. 

She knows she’s way older than you. There’s no need to keep reminding her.

“It's a cliche to say that age is just a number, but when you're learning how to date older women,  your focus shouldn't be on the obvious age gap. Whilst socially it may currently seem a lot more usual to see an older man with a younger woman this trend is likely to shift as women become the main household earners.

So if you meet an attractive older woman don't focus on the date on her passport. A woman of any age wants to feel that she's been chosen by the man she's with because of who she is. Validate her and compliment her on her confidence, her energy, her vibrancy and she will be a lot more engaged than if you tell her 'she looks good for her age”.

Hayley Quinn - HayleyQuinn.com

Hayley Quinn Profile


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