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Mature Dating: Advice To Having an Affair with an Older Woman

Do you remember when you were younger, and your parents insisted that you had to wait until you were old enough to start dating? At the time, there was nothing more annoying than this!

Now that you’re older, you probably understand how love and romance become more powerful and how the desire to meet a partner with a similar mindset grows the more you age.

That is one of the reasons you should consider dating older women!

Whether you date them online or offline, we will discuss how you can impress older women and why having an affair with them is so fulfilling.

Mature Dating Advice: How to Date a Mature Woman

Mature Dating Advice

Figure out who you are

The last thing a mature woman wants to deal with is a lost boy still trying to figure out who they are and what they want.

You do not have to have lifestyle guru levels of having your act together. However, it should be clear that you are working on making yourself a better man and that you know the direction you want to take.

Take care of the wallet situation

There is this assumption that dating an older woman is all about satisfying their cougar needs and getting some form of compensation in return, whether gifts, favors or even money.

Trust me, that is mainly just in the movies.

In real life, these women are looking for equals. At the very least, they do not want to feel like the only reason you are interested in them is because of their money.

Act a few years above your age

Maturity is very important for women of all ages. Older ones, in particular, have a soft spot for a mature man, even when you are several years younger.

The last thing she wants is to feel like an old, cradle robber. So, grow up and meet her at her level! Communicate maturely. Fight maturely. Love maturely.

Show her some respect…

These women have probably seen it all, from major career moves to family drama. Show her some respect, not only for her past experiences but also for the woman she has become. This is actually one of the easiest ways to get into her good graces as mature women are suckers for respect with their affection.

… But keep it fun

Respecting her is not about calling her “Ma’am” and being her yes man. Respect and fun are not mutually exclusive. So, go out of your way to make her feel special and young again. This is exactly what they are looking for when they date younger men, and you do not want to disappoint.

Be confident and take charge

Just because she is older than you, it doesn’t mean that she has to be in charge. Mature women love a man who is confident and can take control of matters. So, reach out first and plan those dates. This will make you infinitely more attractive to her than any other younger guy she may be eyeing.

Take care of yourself, physically

Physical attraction never ceases to be a major selling point in love, and dating an older woman is no different. They, too, love some eye candy, so do your best to deliver. You do not have to be a catalog model with rock hard abs and a killer jawline. Sometimes good grooming and a stylish wardrobe are all you need.

Questions to Ask an Older Woman

What are you looking for in love?

You need to establish right off the bat that you are on the same page as your relationship goals go. You do not want to lead her on when she wants something long term, and you are just in it for fun. Understanding what she is looking for will help you figure out if and how you fit into her life and how she does in yours.

What more would you like to achieve in your life?

These women have seen and done a lot in their lives. Whether she is in her foxy fifties or her forties, she might still have a lot more planned for her career or even personal improvement journeys. This question will help you learn more about her and what makes her special. It also shows your long-term interest in addition to being there for a good time.

What do you expect from me?

In addition to understanding her general relationship goals and intentions, it is important to establish individual expectations.

Does she want you to be her equal partner, or is she looking for more of a sugar baby-sugar momma relationship? Does she expect exclusivity, or is she interested in an open setup?

You need to set these boundaries as soon as possible.

What have you learned from your past relationships?

The beauty of dating an older woman is that they have a wealth of experience to share with you. All you have to do is ask. This is also a sign of maturity and will definitely earn you many points when you are trying to impress her.

What is your idea of fun?

It is not always about serious conversations and important lessons. You also have to know what she considers fun. As the younger person in the relationship, it is unofficially your job to be the commander in chief of all things fun. You should therefore find out what it is she enjoys and find ways to give her a good time.

What makes you happy?

Finally, these women deserve to be happy. And the best way to make them happy is to know what already works. It could be a hobby she has picked up, her work, or even kids if she has any. Whatever the case, figure this out and find ways to incorporate these gems into your interactions to make her feel special.

Benefits of having an affair with an older woman

They like younger men

This might come as a surprise, but older women are really into young guys.

That’s great news for you as you do not have to worry about convincing her to look past the age gap. She is already ok with it and more eager for the adventure than you can imagine!

There is just something about that youthful energy that draws them in.

Maybe it is the fact that the vibe rubs off on them and makes them feel like they are reliving their glory days.

Or it could be that being with younger men gives them a new and exciting perspective on love.

Whatever the case, you can breathe easy knowing that you have something going for you as you figure out how to make your move.

You’ll have great conversations

Older women are mature not only physically but also mentally and emotionally, which makes them great conversationalists!

They have just the right balance of deep thinking and shallow goofiness to make everything you talk about fun. It doesn’t really matter whether you are discussing world politics or the pineapple on pizza debate.

The most important thing for you to do is not to make any assumptions about her. No, she doesn’t want to only talk about work or her kids or her annoying ex-husband. Give her a chance, and you will be pleasantly surprised at how awesome your chats together will be.

They won’t ask you for a baby

One of the greatest fears that young guys have about dating women is that they will be asked to settle and start a family right away. This couldn’t possibly be further from the truth!

Why? Because a lot of older women who already have kids have more or less closed that chapter of their lives.

All they want now is to let loose and have as few responsibilities as they can get away with. So, you do not have to worry about warding off her baby-making advances!

They don’t play mind games

Younger men dating older women do not have to worry about being the victims of mind games.

You do not have to bend over backward, trying to figure out what she wants or means. You do not have to tiptoe around her in the fear that you may fall into one of her many emotional traps.

In these relationships, things are said as they are and dealt with openly.

They are extremely confident and have high self-esteem

One of the biggest benefits of dating an older woman is that they are very confident, sure of themselves, and comfortable in their skin. It means that you do not have to try and boost her self-esteem by continually complimenting her.

Her confidence will manifest itself in several ways, including:

  • The way she dresses.
  • She will speak of herself in a positive light.
  • She knows how to take a compliment.
  • She will be willing to do some pretty exciting things in the bedroom.

Mature women are experienced in every way possible

Older women have seen it all – experienced crush or love and even heartbreak; seen success and failure. These experiences will come in handy when it comes to building something substantial as a couple.

She will teach you to love and fight fair. She will show you how to invest and start successful ventures. In a nutshell, you will have a deep well of wisdom at your disposal.

Nobody will interfere in your relationship

Older women understand the importance of making relationship decisions without third-party intervention. So you do not have to worry about impressing not only her but also her posse of gal pals. They may be important to her, but she has enough confidence in her decisions not to be swayed by their opinions.

They are independent

Another benefit of having an affair with an older woman is the fact that they are independent. First, they are most likely financially independent, as they will have established a career to support themselves.

Secondly, mature women are usually emotionally independent, as well. She will want you, but she won’t need you – no need to play the role of her emotional hero.

Older women are open to learning and trying new things

These women are not know-it-alls. Despite their wealth of wisdom and experience, they are always willing to learn something new.

It means you will have a chance to contribute to the relationship by teaching her how the game of love and romance has changed since she last played.

Here’s what can you teach her:

  • Modern unspoken rules of dating
  • New relationship lingo
  • Sexual trends. Having sex with older women can be really fun! (Remember always to use good condoms to protect yourself from STDs!)

They have realistic relationship expectations

The fact that they have been in several relationships before means that older women know precisely how they work. They do not expect life through rose-colored eyes or a perfect happily ever after.

They will be ready for everything, including:

  • Inevitable fights and disagreements.
  • Love without a price tag.
  • Disappointments because you are both humans, after all.
  • Naysayers from their group of trusted friends and family.
  • External trials that shake the relationship, whether it is unemployment or losing the property.

They are very sensual and sexually liberated

Finally, you have an amazing and profound intimate life to look forward to should you decide to date an older woman. Figuring out how to have sex with older women is pretty simple.

Just follow the three cardinal rules:

  • Follow her lead.
  • Do not shy away from her requests.
  • Be ready to take notes from the sexual maestro that is your girlfriend.

Bottom line

Older gals have a lot to offer, especially if you are tired of the drama of young girls. If you need a break and want to experience real and mature love, you should consider hooking up with an older woman; visit to know more about cougar dating.

In case you are interested in dating a female colleague, check out those signs a married female coworker likes you more than a friend.

Whether she is a few years older or old enough to be your mother, do not shy away. Give her a chance, and you will be pleasantly surprised.

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