How to Ask an Older Woman to Sleep with You in 2024 – Top Tips

As you already know, dating older women is not that easy as dating girls of your own age, and you will really need to take some time to seduce them and make them fall in love with you.

How to Ask an Older Woman to Sleep with You in [year] - Top Tips 4

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Cougars and milfs are a different breed, and they will not fall for your games easily, so you will have to find a way you will make them satisfy your wishes without coming off as way too pushy.

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Younger men often lack the tactics and the knowledge that is needed to seduce older women, but once you get into our article, I believe things will start going a lot better for you.

Here you will find out:

What is the easiest way to make older women get into your bed
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How to Ask an Older Woman to Sleep with You?

1. Don’t Ask Her Directly

I believe this is a pretty obvious piece of advice because no one will accept to sleep with you if you ask them directly, not even the easiest younger girls.

This can make things even worse if there is a big age gap between the two of you, and she will start to think that you are just using her and playing games all the time.

For that reason, even if you have been dating for a month or longer, she will definitely be pushed off by this question.

If you have been able to develop some kind of intimacy between the two of you, let it continue to develop slowly and then find the right moment to suggest getting physical.

Always make sure to listen to her needs and wishes, and if you feel like she is not ready for that yet, don’t try to push it too much on her.

In case you are patient enough, in the beginning, you can really count on being blessed by your woman in the near future because she will never forget how much care you have shown her.

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The more patient you are, the bigger you will grow in her eyes, and the higher the chances will be to get into her bed.

2. Build Up Her Self Esteem

How to hook up with older women is quite easy if you know what the things that will turn them on and make them feel like they are the most attractive human being on earth are.

Men who have the most success in relationships (like eHarmony or Tinder) and casual hookups (like BeNaughty or Ashley Madison) are the ones who know how to build up this woman’s esteem and shower her with compliments.

However, this is not the same as being flirty and throwing around compliments like it’s nothing because it certainly won’t work on all of them.

They are aware that because of the age difference, many young men will say basically anything, hoping to get them into bed, but that is the guy who they will 100% ignore.

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If you want to be the one who will seduce this milf, you need to make sure you give her the compliment she needs and focus on her intellect, humor, and capabilities that are in no way connected with her physical appearance.

Older ladies prefer compliments regarding their knowledge and business success, so make sure you find out how she is standing in these areas and make sure to give her an adequate compliment for that.

This will make her very much attracted to you, and she will start feeling the sexual desire and sexual tensions, even if you have only exchanged a few words.

Trust me, this is the best thing you can do, especially if you are a much younger guy, and once you realize what this woman wants, make sure to give it to her.

3. Build Sexual Tension

This is something that is usually easier said than done, but if you are dealing with a mature woman who knows what she wants, then it definitely won’t be a problem for you.

These women tend to have a lot of life experience, and they are certainly not going on a date with a younger man for the first time.

For that reason, it is very important that you are able to act like an older man and create the atmosphere that they tend to provide them with easily.

Sexual tension is the key to seducing both old and young women, but mature women will get hooked on you for life if you are able to do it the right way.

However, in this case, the tensions shouldn’t be created mainly by physical contact but rather with your eyes and simple, gentle gestures.

Eye contact is the key if you are learning how to meet old women, and they will fall for a man who is able to maintain intense eye contact without problems throughout their whole date.

This will give you the aura of confidence and make you appear completely irresistible in their eyes with ease.

There are no sex tips that can help you get a woman to sleep with you easier than this, and make sure you practice it with every single woman you meet.

It is also the reason why it is so much better to meet these women in real life rather than through dating sites because you certainly won’t be able to make a first impression as good as that through text messages.

You can also use small and gentle physical gestures like touching her hair, her arm, or just being a gentleman and helping her take a seat or enter the room.

These are some of the things that are often overlooked both by younger and older men, and they can make a woman fall for you immediately just because she feels wanted and taken care of.

4. Be Suggestive

If you have already been seeing each other for some time, then how to ask a woman for sex shouldn’t be that hard because you have definitely managed to create an intimate relationship.

After she gets comfortable in your company, you can start hinting at different things and seeing how she feels.

If she responds in a flirty manner, you can be sure that she is interested in you too; even though she may not be up for it right now, there is definitely a chance you will be able to get into her bed in the near future.

In case you see that she is responding well and that after some time, she is starting to hint at these things too, then you could even suggest going to your or her home at the end of the night.

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However, don’t overdo it like many men tend to do and especially don’t use the same phrases you would use on younger women because it can feel way too pushy, and they may start to feel uncomfortable.

Also, don’t use the slang that is popular in the culture these days because they probably understand it but find it pretty childish and immature for a man to use it.

However, whatever you may be talking about, never ever directly ask her to have sex with you and never mentioned that you love to meet older women for sex because you will definitely ruin your potential future with her.

No dating coach can tell you when is the right moment to sleep with her, but her body language for sure will so follow along and listen to her carefully.


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