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How To Ask An Older Woman To Sleep With You: 9 Questions That Will Get You Laid

How To Ask An Older Woman To Sleep With YouGoing from “hello” to actually sleeping with older women might seem hard for you right now.

You don’t have the same experiences yet, so the pressure and doubts you’re having are understandable.

Chances are you’re thinking that you need to be rich or have tons of credentials to get her interest. But that’s not true at all.

You’re just overthinking and making things complicated when they don’t have to be. In fact, the reality is that you have a good shot at getting laid if she is already talking to you.

By simply asking a mature lady the right question, you can turn her on and make her want to sleep with you.

Yet, it isn’t so simple as asking “do you wanna hook up?” out of the blue. Such a tasteless invitation won’t work.

Instead, use one of these refined questions if you want to sleep with her without risking rejection.


1. Is There Something You Want To Do To Me?

This is one of the classic questions that you should ask if you want to get laid fast. It’s straight to the point yet classy since it doesn’t sound vulgar at all.

Furthermore, it’ll increase the sexual tension since it’ll give the air a horny vibe.

With that said, lines like this tend to have the best effect when the older woman you’re going after is aggressive.

You see, a cougar is confident and proactive. Thus she’ll love it when you offer yourself up to her in this manner. She’ll be more than happy to take you.


2. What’s The Wildest Thing You’ve Ever Experienced In Bed?

If you want to get an older woman to sleep with you, this is a great question to ask her. Bringing up naughty memories will certainly make her remember the sexy feelings she had back then.

Hence, this question will not only make her miss being adventurous, but it’ll put her in a lusty mood as well.

And since you’re there in front of her, she’ll connect you with her sexual memories.

In turn, she’ll feel inclined to try them out with you.


3. What’s Your Biggest Sexual Fantasy?

Most women over 40 years old are comfortable with sex and are aware of their sexual desires.

Therefore you can definitely stir up the conversation in this way without embarrassing her.

Unlike young girls, she won’t be shy but instead feel intrigued by this question. It’ll lead to a fun and sexy conversation that will undeniably get steamy quickly.

Once she’s done sharing, you can make your move with, “maybe I can help make them come true?”


4. Have You Ever Tried A Younger Guy?

Do you want to come on strong to a mature woman? Then this is the question you should pick.

There’s no way that she won’t know what you mean, especially if you’ve been hitting on her.

Not to mention, you’re basically telling an older woman that you want her without directly saying it.

Besides that, it’s also what you should use if you’re going to play it safe.

Since you’re only insinuating your intentions, you can easily back off should she react negatively. She can’t reject if you never ask her out in the first place.


5. If We Did It Your Way, What Would You Want Me To Do?

Given their experience at their age, 40-50 year old women know what pleases them in bed. Apart from that, they’re not afraid to express what turns them on.

For this reason, this question will increase your success rate. The reason is an older woman will want to sleep with you if you show her that you want to know what she prefers.

She doesn’t have any energy or patience to endure lousy sex anymore.

So follow up this line by letting her know that you will follow her instructions to satisfy her body.


6. What Do you Think About Leaving This Place With A 25 Year Old Guy?

When an older woman shows you clear signs that she’s into you, you can take a confident approach towards her.

In this case, you can be bold and ask this question while you’re outside, such as a club or bar.

Of course, at this point, you both know what exactly you’re talking about.

But although you’re being obvious that you want sex, it still won’t come off as disrespectful.

On the contrary, your polite way of being forward will appeal to her. It’ll likely make her want to sleep with you.


7. Can You Guess The Color Of My Underwear?

Now this question may rub some women the wrong way since it’s arrogant.

This is why you need to make sure that you only use this on mature women that have shown solid interest in you beforehand. Also, the right contest plays a vital role.

It’ll definitely create a sexy atmosphere and max the horniness level between the two of you.

You can further entice her and add, “want to see?”


8. Do You Know What You’re Making Me Think?

Is your style a combination of flirty and naughty? If yes, this question is perfect for you.

It’s another classic line that’s commonly used if you want to tease someone you have the hots for.

Now when you convey it to an older woman, she’ll be flattered and excited at the intensity.

Not to mention with the way the sentence is phrased, you’re essentially saying that you can’t stop yourself from thinking about her body and wanting to bang her.

This will make her feel sexy and aroused, making her want to try you out.


9. When Do You Think You’re At Your Sexiest?

Want to instantly charm an older woman and get her to sleep with you?

There’s no better way than to make her feel that she’s sexually attractive in your eyes. You can do this by answering the question after she explains her answer.

Cause no matter what she may say, there’s only one answer that you have to give in order to score with her. And that is, “right now.”

Knowing that you think she’s hot will make her feel like a young woman again. On top of that, it’ll raise her confidence a lot since a young guy like you fancies her.




  • Tom Phillips

    Tom Phillips is a Dating Coach for World Hookup Guides who has been helping men to succeed with women for almost 7 years. His coaching career began with one-on-one coaching and has gradually evolved into seminars. He has dated successfully dated several women over the years and now shares strategies and techniques on several national publications in addition to World Hookup Guides.