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How to Flirt With Older Women and Get Great Results


There are many ways to discuss how to flirt with older women.

Some methods are dull and redundant, whereas others are powerful and efficient.

Since you’re obviously interested in the latter, we will spare you a discussion of methods that ultimately give you lackluster results.

Flirting with older women may seem difficult at first, but like all things you get better with practice. It doesn't matter where you meet them, though we do have a few favorite places that have been great for meeting older women, these techniques and principles will work for you.

Try them out and see just how much better the responses you get are.

The Easiest Way To Meet More Single Older Women
(According To The Experts)

If you really want to get good at flirting with older women you need to find a way to constantly meet them. The easiest way we've found is online since most older women are meeting guys online now, many ONLY look online.

There are a lot of apps out there but not many are great for meeting single older women. These are the best options right now that consistently work for normal guys still learning how to flirt:

SiteOur ExperienceOur RatingFree Trial Link
Best For Relationships
Experience Highlights
Experience Highlights
  • Easily the best option for long-term relationships
  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
Try eHarmony
Best For Casual Fun
Experience Highlights
Experience Highlights
  • The best way to meet women for casual relationships
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
Try AFF For Free
Decent For Younger Guys
Cougar Life Highlights
Cougar Life Highlights
  • Focused on younger men meeting older women
  • A mix of relationships and hookups
  • Growing
  • Not as popular as eHarmony of AFF
Try Cougar Life

How to Flirt With Older Women

The biggest hurdle to overcome initially would be a fear of talking to older women. Being scared and losing your confidence is a big mistake when making the first move on an older woman.

While this fear may not necessarily be debilitating, you could probably attest to the increased anxiety a younger man feels when trying to flirt with mature women.

We’re about to go over how to flirt with older women successfully so that you can get great results.

Whether it is for a first date, an eventual relationship, or even just fun daily interactions with the attractive older women in your day-to-day life, you’ll learn what it takes to maximize your flirting to get the results you’re looking for.

Even though it may feel perplexing at times, flirting with older women is not very different from flirting with younger women.

Some guys think there’s a puzzle to solve when it comes to dating and interacting with women that are older than them when in reality, all it takes is a little more finesse.

New course

There’s also an upside to flirting with older women – they are much more forgiving than their younger peers, especially when you're in the places that make picking up cougars really easy.

Provided that she’s attractive, younger women have a variety of options at any given time.

That’s because the majority of men have a preference for younger women.

Those cute girls in their 20s are at a prime age for dating a wide range of men.

Most of your male peers will focus on flirting with girls who are just a few years younger than them.

This means that there is much less competition for older women.

As a result, younger women are highly selective about who they date while older women will actually give more thoughtful consideration since they are not spoiled on choices.

In regards to them being more forgiving, it simply means that you won’t have to be so meticulous with your approach.

Your flirting with women over the age of 35 won’t have to be perfect.

The way you ask her out won’t have to be perfect either.

Your presentation to her will never need to be flawless.

In many ways, flirting and dating attractive older women is a more fruitful endeavor.

Moreover, since this guide focuses on how to flirt with older women whether at work, at a bar or online, here are two principles that you should keep in mind.

Teasing and rapport is critical when learning how to flirt with older women

No matter her age, you should be teasing the women in your life, because it is simply the best way to flirt with women.

Nothing excites a woman more than a man who is able to make her laugh and doesn’t take himself too seriously.

Teasing has the added bonus of pushing her emotional buttons and stimulating an attraction for you as a result.

So call her immature.

Lightheartedly pester her blunders.

Tease her, and smile as if it’s a joke that only you understand.

The better you get at teasing, the stronger the effects will be.

Eventually, older women that are receptive to you will no longer be able to help themselves around you.

That’s when you’ll see highly overt signals of interest such as touching and lingering eye contact.

In addition, rapport is also an important concept to keep in mind.

You must build a comfortable connection between you and her to get her to flirt back.

In other words, she must trust you and feel a connection to you.

This applies especially if you met her through online dating.

But it also applies to the women that you work with or see on a weekly basis as well.

The best way to build rapport is to engage her in lively conversation and show that you’re a man that can be trusted.

In regards to the latter, as long as you don’t rush the flirting process, you should be fine.

There’s no need to try and rush a first date or anything thereafter.

Allow the chemistry to flourish naturally.

The more you talk, the more you tease, and the stronger her attraction for you becomes, the stronger your bond and the more willing she will be to take things further with you.

Be flirty, be challenging, be somewhat mysterious, smile plenty, act confident – and you’ll have great results with older women.

How to Flirt With Older Women Online

Lastly, we’d like to make a note on online dating.

Although your mileage may vary, generally speaking online dating is a great place to meet keen older women.

If you have not tried it, check out our list of the best websites for dating older women.

The advantages of meeting these women online is that you’re probably not going to have to worry about her being in a relationship, since you’d be meeting her on a page for singles.

Meeting available older women at work or throughout your daily life can be challenging in this respect.

Here are a few pointers and observations to help you maximize your flirting with the older women that you meet online:

  • Be friendly
  • Have your best pictures on display; professionally-taken if possible
  • If she’s talking to you and continuing the conversation, she likes you, and don’t doubt it
  • Overthinking is one of the biggest flirting mistakes you can make; older women are much more direct than younger women so there’s no need to overcomplicate your approach
  • Try to get her number as soon as possible and move your conversation over to text message
  • Don’t try and make plans too soon; first get her number and start talking over text
  • Don’t forget the importance of teasing and rapport

There are plenty of available and willing older women to meet online.

Many of them are gorgeous and have great personalities.

Don’t hesitate; older women reward bold behavior much more than younger women.

So go after her shamelessly, don’t see the age difference as a problem, and have fun flirting with her.

Starting a conversation and being able to continue it is already 50% of the battle.

Now all it takes is a follow-through.

There are many wonderful older women out there, so find them, flirt with them, and see where things go from there. Pay close attention to how she reacts to your flirtatious endeavors because older women flirt differently from younger ones. You want to know if she's flirting back with you!


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