Dating mature ladies as a younger guy

[jt17574]

Hello bros, just curious if anyone here has ever dated someone much older?

I'm in my 20s but somehow managed to land a date with a lady in her 40s. Didn't really expect it to happen but a bit excited and nervous haha

If you have been in similar situation:

How did it went?
What were the biggest differences between you and her?
Normally, what do these women look for in younger guy? companion? sex? serious relationships?
Anything I should know or watch out for?

Would love to hear bros life experiences and advice. :D

[waterblaster]

Just don't expect a virgin

[viper]

Just go with the flow. Don't even think about age. Its just a number. Have fun and see where it leads too. Maybe NSA or ONS?

[looney83]

Hello bros, just curious if anyone here has ever dated someone much older?

I'm in my 20s but somehow managed to land a date with a lady in her 40s. Didn't really expect it to happen but a bit excited and nervous haha

If you have been in similar situation:

How did it went?
What were the biggest differences between you and her?
Normally, what do these women look for in younger guy? companion? sex? serious relationships?
Anything I should know or watch out for?

Would love to hear bros life experiences and advice. :D

be prepare to have many rounds.

most guys at 40s cannot do more than twice..

[evilair]

Hello bros, just curious if anyone here has ever dated someone much older?

I'm in my 20s but somehow managed to land a date with a lady in her 40s. Didn't really expect it to happen but a bit excited and nervous haha

If you have been in similar situation:

How did it went?
What were the biggest differences between you and her?
Normally, what do these women look for in younger guy? companion? sex? serious relationships?
Anything I should know or watch out for?

Would love to hear bros life experiences and advice. :D

She is already in her 40s, so she knows what she wants. If you can bypass the first 2 dates, you are almost guaranteed to get into her pants.

Be nice and a gentleman. Don't expect any action on the first two dates, but make sure to show interest in her. Always look into her eyes and not her boobs when you talk to her.

And if she caught you checking out her boobs and butts. Just give her a friendly smile and compliment her, something like "that's a killer ass".

On the 2nd date, try to hold her hands and kiss her cheeks..

On the 3rd date, try to engineer something for intimacy. She is already in 40s, so she will know what you are trying to do and would probably be ok if she likes you. If she tries to be playful and asks you, "What are you trying to do?". Don't answer her directly, instead ask her if she is ok with it. Something like "You already know what I want. Will you be agreeable to it?" If she does not say "no", then it is a yes already.

Just make sure you give her more than 3 rounds to get her hooked.

Tell us how it goes, and a bonus if you can upload some pictures. Good luck and all the best!

[waterblaster]

She is already in her 40s, so she knows what she wants. If you can bypass the first 2 dates, you are almost guaranteed to get into her pants.

Be nice and a gentleman. Don't expect any action on the first two dates, but make sure to show interest in her. Always look into her eyes and not her boobs when you talk to her.

And if she caught you checking out her boobs and butts. Just give her a friendly smile and compliment her, something like "that's a killer ass".

On the 2nd date, try to hold her hands and kiss her cheeks..

On the 3rd date, try to engineer something for intimacy. She is already in 40s, so she will know what you are trying to do and would probably be ok if she likes you. If she tries to be playful and asks you, "What are you trying to do?". Don't answer her directly, instead ask her if she is ok with it. Something like "You already know what I want. Will you give it to me?" If she does not say "no", then it is a yes already.

Just make sure you give her more than 3 rounds to get her hooked.

Tell us how it goes, and a bonus if you can upload some pictures. Good luck and all the best!


My 3rd date was an overseas trip :eek:

[LordVader]

Just don't expect a virgin

Maybe backdoor is virgin leh?

[Fabil]

My 3rd date was an overseas trip :eek:

Wow, where? Stay in hotel room piak piak?

[Fabil]

Hello bros, just curious if anyone here has ever dated someone much older?

I'm in my 20s but somehow managed to land a date with a lady in her 40s. Didn't really expect it to happen but a bit excited and nervous haha

If you have been in similar situation:

How did it went?
What were the biggest differences between you and her?
Normally, what do these women look for in younger guy? companion? sex? serious relationships?
Anything I should know or watch out for?

Would love to hear bros life experiences and advice. :D

Is she single, married or divorced?

If they are dating a younger guy, probably looking for sex. Just remember to focus on pleasuring her first.. then u will really unleash the nympho and have the time of your life. If she not experienced, she will be v eager to learn.

[sony2002]

are you treating her as gf (future wife) or just sex buddy?

I think this is something that both of you need to align. Older ladies most likely want to settle down, are you ready for that?

[shadymassage]

if sex buddy go ahead, older women more experienced and can be horny

[loneyheart]

She is already in her 40s, so she knows what she wants. If you can bypass the first 2 dates, you are almost guaranteed to get into her pants.

Be nice and a gentleman. Don't expect any action on the first two dates, but make sure to show interest in her. Always look into her eyes and not her boobs when you talk to her.



I disagreed bro " Don't expect any action on the first two dates "
But agreed she know what she want if not will not date a younger guy tat can be her son
So up her if u may for 1st date b4 she changed her mind :)

[jt17574]

Thanks bros for the kind advices. I will update you on how it goes. Heres a bit more information if you dont mind a long read.

At the start I didn't really have much expectation, was just swiping wechat out of boredom when she caught my eye. Although she looked visibly older, she gave off a really elegant, calm vibe and looked really good for her age so I sent her a DM. Somehow she replied and added me as friend. In the next few days, we chatted here and there. I also told her that I got out of a long term relationship earlier this year and am not looking for anything serious but later on she still asked me to bring her out of a date. She seem to be interested in me, quite responsive in chat and asking me personal questions like what is my type etc.

But I'm still not sure what she is looking for though because she sort of reminded me a few times that she is older and subtly told me that she kinda minds the age gap between us. I told her that i really dont mind her age and we can just meet with no expectations first and see how it goes. She also seemed surprised to hear that I do not mind her age. Personally, I'm looking for something casual, mid to long-term depending on how things go.

In my mind, I feel that it doesnt make sense for her to go on a date with a much younger guy if she is after something serious because the chances of things working out is very much slim.. Also, this is her first time dating a younger guy so i figured she might be self-conscious about it. I will listen to bros advice here, go with the flow, make her feel comfortable and if things go well, we can move on to more fun things :D


Just go with the flow. Don't even think about age. Its just a number. Have fun and see where it leads too. Maybe NSA or ONS?

Yea, I told her its just a number for me too, what matters is if we're comfortable with each other and happy together. Hopefully it leads to something more later on haha


be prepare to have many rounds.

most guys at 40s cannot do more than twice..

Then it shouldn't be an issue for me, I still manage 4-5 times a night :D:D


She is already in her 40s, so she knows what she wants. If you can bypass the first 2 dates, you are almost guaranteed to get into her pants.

Be nice and a gentleman. Don't expect any action on the first two dates, but make sure to show interest in her. Always look into her eyes and not her boobs when you talk to her.

And if she caught you checking out her boobs and butts. Just give her a friendly smile and compliment her, something like "that's a killer ass".

On the 2nd date, try to hold her hands and kiss her cheeks..

On the 3rd date, try to engineer something for intimacy. She is already in 40s, so she will know what you are trying to do and would probably be ok if she likes you. If she tries to be playful and asks you, "What are you trying to do?". Don't answer her directly, instead ask her if she is ok with it. Something like "You already know what I want. Will you be agreeable to it?" If she does not say "no", then it is a yes already.

Just make sure you give her more than 3 rounds to get her hooked.

Tell us how it goes, and a bonus if you can upload some pictures. Good luck and all the best!


Thanks bro for the solid advice, will listen to you and see how it goes. I will definitely give an update


Is she single, married or divorced?

If they are dating a younger guy, probably looking for sex. Just remember to focus on pleasuring her first.. then u will really unleash the nympho and have the time of your life. If she not experienced, she will be v eager to learn.


She is single, told me she don't have luck with guys in general and her last relationship was ages ago and lasted less than a year.



are you treating her as gf (future wife) or just sex buddy?

I think this is something that both of you need to align. Older ladies most likely want to settle down, are you ready for that?


Thats the thing, I'm looking for something casual and i told her im not looking for something serious right now. Nonetheless she still asked me to bring her out on a date. Personally I feel that with such a wide age gap, she should also know there's huge obstacles we need to face in order to settle down so I don't think she is looking for something serious either but will definitely discuss this with her when we meet.

[jt17574]

if sex buddy go ahead, older women more experienced and can be horny

Haha I have been with older women but not with such a wide age gap. They are sure fun to be around with.

I disagreed bro " Don't expect any action on the first two dates "
But agreed she know what she want if not will not date a younger guy tat can be her son
So up her if u may for 1st date b4 she changed her mind :)

Thanks bro for your perspective, wont try to push things too far but will try my best :D

[loneyheart]

Haha I have been with older women but not with such a wide age gap. They are sure fun to be around with.



Thanks bro for your perspective, wont try to push things too far but will try my best :D

Yes bro slow n steady to test the water .... yr sweet words to tease her n see her body language ... if she responded positive she will like u to take the 1st move .... mostly this type r good in bed :)
Will be on for further connection or not will depend of yr performance

[waterblaster]

But I'm still not sure what she is looking for though because she sort of reminded me a few times that she is older and subtly told me that she kinda minds the age gap between us. I told.[/QUOTE]

It happens. Don't show desperate, tease Abit when she initiates but not too much. You will enjoy the night

[Fabil]

My experience with older women is that if you go sensual on them, target their sensitive parts like ears, neck, nipples and eat their pussy, they are pretty much yours.

[waterblaster]

Wow, where? Stay in hotel room piak piak?

Still proceed with the plan during the day and got raped at night. She gave me one of the best experiences altho cannot cip.

[fwchong]

I saw a couple, lady in her 40s and a young man in his 20s following a local Singaporean tour group to Europe.

I can see that lady does all the buying and the guy is the porter that help her carry and the shopping bags. She has nice taste and the guy is enjoying the moment, she will treat you the best places to eat and the expensive watches that she can offer to you....they dont give a F**K what people think. Common...this is 2025, woman and man are equal and so dont feel bad if a woman buy stuff for you.

[Cryptor]

王阿姨好，王阿姨妙
王阿姨包里有钞票

[peregrene]

Like someone said just go with the flow. See how it pans out. Age is after all, just a number. Good luck