40, male here. Stable job, stable and good income, dated before but no sexual experience. Not a moral stance. it’s just how life unfolded.

Lately I get labeled “immature” because my mindset is pretty youthful.

With women closer to my age (mid-30s to mid-40s), things often feel complicated—everyone’s carrying history and sometimes it drifts into a transactional vibe.

With women a bit younger (mid-20s to mid-30s), I’ve noticed early career success can come with quick character judgments.

With women in their early 20s, I actually find it easier to connect. It’s not about “taking advantage”, I’m looking for a long-term, committed relationship. Being older makes me want to show up steady, respectful, and protective so we can build something simple and good.

Is this just me? Do I need to present myself differently? Any tips from people who’ve navigated:

Being 40+ with no sexual history

Getting misread as “immature” when you’re just upbeat/young-at-heart

Bridging different life stages without it feeling transactional

Posting this partly because modern dating is absurdly funny
also genuinely curious what others think. Roast me or coach me

TL;DR: 40, Male, no sexual history, young vibe. Same-age dating feels complex, early-20s adults feel easier to connect with. How do I avoid the “immature” label and find the right fit for a long-term relationship?

This post has been edited by Fabrication: Sep 28 2025, 10:46 PM

what are you looking for in a relationship

if you say that you lack sexual experience, then do you want to start practicing it?

are you relatively physically healthy

are you looking to settle down and start a family.

if so then you need to ensure that you can continue to support your child after retirement age of 60

What I’m looking for
A long-term, committed relationship aimed at eventually settling into family, built on kindness, laughter, and sharing everyday moments. No rush. What matters is mutual respect, clear communication, and showing up for each other in life’s big and small moments

About sexual experience
I’m just being upfront that I have no sexual experience. I’m not looking to “practice” casually, I’d prefer intimacy to grow naturally within a committed relationship. No 'cheong' for me

Health
Yes, healthy and active. I just did a half marathon run this year, 172 cm / 75 kg, and not bald 😄

Finances
Stable career and long-term planning (EPF/savings/investments). I’ll make sure to have a realistic plan to support children

This post has been edited by Fabrication: Sep 28 2025, 10:14 PM

TS, i can see that you really mean it when you say that you are young at heart.

unfortunately, as I have told many of my younger female colleagues / friends in the past, no matter how young you look IC never lie.

your current approach to dating is more suitable for someone who is still in the 20s or early 30s at most.

once you get into your mid 30s and in your case already 40s, the approach has to change to something more practical, realistic and serous.

if you follow your approach, it will take you some time to really find your partner, settled down and eventually have kids.

by then, you could be already close to 48 to 50 and by the time you retire, your kids are only like 10 to 12

also how old is your partner going to be

if you find a more matured partner, they won't wait for you.

your targets should be female about 10 years younger than you so can still have kids

but only get married if you want kids, else better stay single and go for Sugar baby

good luck TS, don't feel down or suicidal

live your life day by day

what you need to do first is to get laid

and another point, do you really know your sexual orientation and preference

could be one of the reasons keeping you down


This post has been edited by cfa28: Sep 29 2025, 01:30 PM

Hi TS, I'm concerned with your thread tag that you're suicidal, but I don't know enough to advise effectively... Specifically speaking, I feel disconnected with gen Z (20s?) and I think I'm very biased against them, so I can't make fair comparisons. For now I'd like to understand your stories first.

Please elaborate on "transactional vibes". What made you think so and how you feeling about those incidents?
On similar note, what made you conclude you were taken advantage of by those in 30s-40s? How does that contrast with those in 20s?

I don't understand quick character judgement part -- who's judging who?

"Do I need to present myself differently?" Depends.
1. Do you hate your current self? If yes, which parts?
2. Imagine dating yourself, what do you think? E.g. ok, funny, or disgust..
3. What kind of partner are you looking for? E.g. if you want a wifey material, club isn't where you'd want to find a girl.

What of you that made others label you immature?

Any young-at-heart examples/description of yourself?

Your current thinking seems framed only from your own angle. That is exactly the line that separates the immature from the mature.

Let me be the “bad guy” and put some hard questions in front of you: At 40, you say you wish to marry and have children. To raise them until they graduate takes at least 23–24 years. By then, you’ll already be 63 or 64. From the children’s point of view — just as they are ready to experience life for themselves, they may already need to carry the weight of looking after you in old age. If money is not the issue, have you considered that time is the real issue?

If this is the starting point for them, what kind of freedom have you really given? Is it a blessing, or simply a burden passed down? When they go looking for their own partner, will they carry joy, or will they carry the hidden burdens of your choices?

You call your job and finances stable. But stability is never a permanent state. Retrenchment, illness, early retirement… many people face these before even reaching their 50s. What makes you think you’re exempted?

And if you marry someone in her 20s or 30s, don’t forget: when you retire, the main responsibility of raising children will fall on her. Does she truly understand what that means, or will she only discover it when the road is already too steep to turn back? One already retired, the other still working — it’s a mismatch of life phases. These are not comfortable questions. They are reminders that choices today don’t just affect you — they echo 20–30 years ahead, shaping the lives of the next generation.

At the end of the day, if you still decide based only on your own angle, ignoring what your future wife or children may face, that’s also a choice. But remember this: every choice becomes either a warning for others to avoid, or a story for others to follow.

I don't think you're being completely honest with why you're being labelled as immature. My guess its nothing to do with being "young at heart", but you really being immature.

Otherwise, why would you not be clear about it in the first post but skirt around it?

I also have zero sexual experience. For me I focus solely on my non negotiable before anything else. These are traits that I want in a woman. Without these traits, there is no second look/date no matter how hot she is.

If you are introvert like me, then your only options would be dating app (I recommend CMB but make sure to pay for it) or speed dating or both. I use CMB and found my soon to be wife. Speed dating I went once only cause per session it's like RM150.

Make sure the woman have what you want before continuing. Be firm on this. Go out talk with them.

This post has been edited by Ramjade: Sep 29 2025, 05:11 PM

Appreciate the straight talk
I’m young at heart, but I plan practically: time, finances, and family

Age/timeline: I understand the math. I’m open to someone younger, but shared values, health, and mutual readiness matter more than a number

“Just get laid”: Not my approach. I’m not looking for practice or any sugar arrangement. I want intimacy that grows within commitment

Orientation: I’m clear on mine. Having little sexual history isn’t confusion, it’s just how life unfolded. No rush

I hear your view. Mine is to choose carefully, act intentionally, and build something that lasts, without compromising my values

Thanks for the concern
Quick safety note: I’m not suicidal
The tag came from LYN thread context, I’m here for perspective, not crisis help

On “transactional vibes” (mid-30s to mid-40s)
By that I mean dates that feel like a checklist or negotiation instead of two people connecting

Things I’ve run into:
Early focus on income/assets or the “ROI” of a relationship
tick and tact game: If you don’t do X, I won’t do Y
Keeping score or performative caring, instead of genuine curiosity/kindness

On “quick character judgments” (mid-20s to mid-30s)
I’ve been labeled “immature” for having a young vibe (playful, optimistic)
For not having sexual history — some assume that means naive or repressed
I try not to judge that fast, I ask questions before concluding

On early 20 somethings
I’ve often found the tone more open and less cynical

Not saying “20s good, 30s/40s bad”, just my pattern so far lah...

Do I hate my current self?
No. I’m content and still growing

Would I date me?
Yes! steady, honest, playful
Growth areas: firmer boundaries and shorter explanations.

What I’m looking for
Warm, respectful, low-drama partner who wants long-term and teamwork. (And no, I’m not looking in clubs.)

What gets me labeled “immature”?
Playful humor, idealism, saying no to casual hookups, and being open about my lack of sexual history. That’s me, I’m fine owning it.

Young-at-heart examples
I stay active, keep learning, laugh easily, and prefer simple days over status games, while managing finances, planning, and health well

This post has been edited by Fabrication: Sep 29 2025, 07:20 PM

Thanks for asking the hard questions
Genuinely welcome any blind-spot checks

On time & age
You’re right about the math.
My philosophy is different: raising children isn’t about them taking care of me later. I don’t believe in “养儿防老”
Even with my precious fur daughter (dog), I raise her well because I love her, not expect a return in the future.

On job stability
You’re right about job stability isn’t permanent, I have seen a lot in my career.
My philosophy is different: I’ve been a bit of a workaholic and, being single, I’ve saved aggressively. If I lose my job, I’ll be okay. That said, I still plan for downturns rather than assuming they won’t happen

On “burdening” a younger partner
You’re right about a partner isn’t a life jacket. It’s someone to share life with.
My philosophy is different: We are in different life stages, but my stability gives me flexibility to shoulder more when needed
Eg. I’d actively encourage and support her pursuing her career dreams if that’s important to her
this could be discussed upfront, but having flexibility, I can do more in life to support the unexpected

On being “me-centered”
Point taken.
My philosophy is different: Live my way, keep personality without losing responsibility
I’m young at heart, not casual about consequences. I’d rather be upfront and move intentionally than rush into something romantic now that reads like a warning later. If we were not happy, could not come to an agreement, the trade-offs don’t add up, that simply means we’re not a match, and I’ll walk away

If you spot gaps in this framework, I’m open to concrete tweaks

explained in Post #10
If you’re seeing something else, I’m open to specifics

Appreciate this and congrats on your soon-to-be wife!

I’m aligned on the non-negotiables approach. Mine are: kindness, honesty, low drama, long-term intent, respect for boundaries, and a sincere, cooperative mindset. If those aren’t there, I walk, no matter how hot she is

CMB tip is helpful! I don’t mind paying
I’ve tried speed dating, but 5 minute speed interview with each girl tend to reward snap judgments over real understanding...

the key to speed dating is to say Yes to as many girls that you meet. i got friends who met their partner through speed dating

u're in your 40s and loaded with cash

just go to any online dating site

ask girls out and take them out

go and have fun. It's completely ok to date more than one girl at a time

enjoy your life

no casual dating for me

ok, i should probably change my strategy..

You need to go out with lots of girls. This was what my friend told me. Tell the girl upfront what you want and what you are looking for. It is very unromantic. But it helps to save your time and the girl time.

Then go for cheap place for first date. Ideal place parks, sushi zanmai.

If a girl cannot accept a normal or cheap place, walk away.

What I'm seeing, is a lot of projection with little grounding.

You kinda give off the same vibes as this dude:

I’m not here to prove myself
I am an engineer, I know what net worth is
If you see something concrete, name the behavior and I’ll address it. Otherwise, let’s skip the projections