How to Flirt With A Milf in 2024 – Success Guaranteed

If you are a young guy who is sure that he has a preference for older, mature women, then you have definitely thought of different ways to flirt with a milf.

Flirting with a milf is a bit different than flirting with younger women, and you will really need to take some time and learn the skills and techniques before you engage in it.

The age difference will be of no problem if you know the right way to spark interest in a woman and if you manage to keep her amused long enough.

If you are looking for tips that will help you hook up with gorgeous milfs easily, then you are in the right place because we know all the ways that will make these women go crazy for you.

I will tell you all about:

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How To Approach Milf Women?

The most important thing that can completely determine your destiny with these women is the way you get to know them and approach them.

Milf women are mature and confident, and they don’t like men who are beating around the bush and don’t have enough courage to approach them directly.

If you know this woman in real life and you believe that she can be a cougar or a milf, you shouldn’t go around and ask her friends about her marital status, kids, and similar things.

The best thing you can do is approach her directly and ask her all the things you want to know.

Older women don’t like to waste their time, so if they are not interested in you and they don’t want to engage in any sort of dating, they will be open about it.

If you are seeking each other quite often, the best way you can catch her attention is through intense eye contact, and trust me; you will be able to see whether she is up for it or not easily in her eyes.

In case she doesn’t seem to respond or react to you in any way, you should forget about her and start flirting with other women.

Many people engage in flirting with older women through different dating sites, so young men can really take time and think about every step thoroughly before they make it.

However, even if you are messaging on Tinder or some other free sugar momma websites, you should be very straightforward, tell her what you want, and ask her all the things you want and need to know.

Be open about whether you are looking for a simple hookup (like BeNaughty or Ashley Madison) or a long-term relationship (like eHarmony or Tinder), and never promise things you know you won’t be able to do.

However, flirting online and flirting in real life tend to be much different, especially when it comes to milf flirting, so we will cover both of these options.

How To Flirt With An Older Woman In Real Life?

If you have already tried cougar flirt or milf flirt, you probably know these women are nothing like younger girls, and you really need to try a lot harder if you want to impress them.

Flirty milfs like to provoke men, especially younger men who often feel a bit shy or don’t have enough confidence in their presence.

I believe that you want to be the one who is dominant in this game and that you want to have the main word, so get on board and read these pieces of advice carefully.

1. Don’t be cheesy

Cheesy pick-up lines may work with young and dumb girls, but older women have decades of life experience, and they can spot a liar and a cheater immediately.

They are not attracted by quotes you can see in movies and those dating guides, and you will certainly need to be a bit more original if you want to keep their attention.

The best way you can approach her is by a simple “Hi” or “Hello,” and you don’t really need to come up with God knows what in order to impress her.

Be natural and confident, and show sincere interest in her because this is the only way she will consider opening up to you.

2. Bring up an interesting topic

Older men are always caught up with the latest happenings in the world and in their country, and they are knowledgable about many interesting topics which makes it easier to start a conversation with a beautiful milf.

This is something you should be doing too because older women need to be intellectually stimulated in order to become interested in you.

They need to see that you are not a 25-year old who has no interests in life besides dating older women and trying out different fetishes.

Show her that you are a valuable man and that just because you’re one of the younger guys, it doesn’t mean that you have no goal in life.

3. Don’t be dramatic

Younger guys tend to be overly dramatic about everything, and that usually shows that they don’t have too much confidence and self-esteem, so make sure you control yourself when it comes to this.

Never talk about crazy exes or work colleagues, and don’t bring up your dramatic experiences, at least not at the beginning when you are still trying to catch her attention.

Things like this will only make you feel bored and show that you are a useless child, and she will replace you with someone much older and more stable.

4. Show that you are interested in kids

When dealing with a milf, you will definitely have to hear about her kids at some point, whether they are newborn babies or college students.

I would suggest always being patient and listening to her talk about them because it will show that you are sincerely interested in her and her life and that you don’t mind hearing about topics that have nothing to do with you.

Most people who don’t have kids get irritated by these stories, but if you are flirting with a milf and considering engaging in something more serious with her, you will have to get used to it.

5. Shower her with compliments

This is pretty much obvious, but you really have to know when to give a compliment and what kind of compliment she will enjoy.

However, giving out compliments to milfs and cougars is a bit different in comparison to younger girls, and they don’t really want to hear how great their boobs are.

When flirting with a milf, the best thing you can do is compliment her on the love and time she takes to care for her kids; tell her how much you admire women who are mothers but still find time for themselves, especially if they are a single mom.

After you have given her some compliments regarding her dedication or intellect, you can also compliment her on how good she looks, but never give direct compliments because it may create a weird atmosphere.

6. Never use the word milf

The moment you say “Milf” she will turn her head and go to a different man, so it is very important to never mention things like this in their presence.

Milf is a term that is pretty much misunderstood in popular culture, and you can only create problems for yourself if you decide to use it.

This may work fine when online dating, but the best and most important dating tip you will need to remember every time you start flirting with a milf in real life is to never use this term.

7. Don’t brag too much

As we have already mentioned, older women are a lot more delicate and sophisticated, and they detest guys who brag all the time, whether it be about their experiences, money, or something else.

If you have had a hot model ex, or you are the highest-paid lawyer or broker in your company, you should just keep these things for yourself.

Mature women are pushed off by guys who spend all the time bragging about themselves but never asking the other side about what she is doing in her life.

8. Spark some sexual tension

While talking to her, you need to spark some sexual tension if you want to keep her interested, and you should hint at some naughty things from time to time, but make sure not to overdo it.

You can touch her arm from time to time, keep your hand on her leg, or something else simple like this.

It will allow you to see whether she is interested in you or not, and you may be able to completely change her attitude towards you.

9. Never talk directly about sex

Even though you certainly have a lot of sexual desires that you would want to make come true with this milf, you should never be direct about it, especially not while you are still flirting.

Rather leave this for the official first date and keep the directness for later because you don’t want to lose her too soon.

Older men never do this, so you should be very careful and make sure you don’t start initiating the best sex ever yourself because it is a very touchy subject with these women.

How To Start Flirting With A Milf Online?

We have covered things you can mess up when you are flirting with a milf in real life, but you should be very cautious when texting them too.

Online dating can be very sketchy, and sometimes you don’t even know whether you are engaging in milf or cougar dating before you manage to hold a brief conversation with this hot woman.

For that reason, I recommend checking out as many details and information as you can about this woman before you start sending her text messages all the time, especially if you are using a platform like this for the first time.

If you want to make sure your online milf will fall for you and propose switching from DMs to real-life flirting, these are some of the things you should try to do.

1. Be direct

When online dating, things are a lot easier, and you don’t have to worry about sounding too pushy because you don’t want to waste your time texting the wrong people.

The moment you match or like someone on an online dating platform, you should start texting them, ask them all the information you want to know, and be explicit about the things you are looking for from a potential hookup or a relationship.

You also shouldn’t worry about using terms like milf because they usually label themselves that way, and they definitely won’t mind it.

Sometimes they also say what type of relationship they are looking for in their profile bios, so you should check this out before you start messaging them.

2. Get her phone number

If you think that she may be a good choice, I recommend ditching social media and online dating platforms and asking her directly for a phone number.

This will make your communication a lot easier, and it will allow you to schedule a date a lot faster than you would throughout dating platforms.

It will also show that you are serious about getting to know her and dating her, which will give you a big plus in her eyes.

3. Tease her

Just like in real life, you have to spark sexual tensions somehow, and I believe the best way to do it is through sending flirty texts.

If you are confident enough, you can start exchanging sexy pictures and nudes too, but overall, I believe a simple text will also do the work.

You shouldn’t hesitate to do this because older women are much more confident about themselves than younger ones, and they will be open to exchanging this type of message with you.

4. Don’t overthink

Older women really don’t judge, and you can feel free to do and say anything in their company because they will not take it to heart.

You should feel free to text them anything you want, and you shouldn’t worry too much if you make some sort of mistake because they will forget it in a day or two.

They are very easygoing and mostly focus on themselves, so you definitely won’t feel uncomfortable around them.

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