QUOTE(Fabrication @ Sep 28 2025, 07:28 PM)
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?
Your current thinking seems framed only from your own angle. That is exactly the line that separates the immature from the mature. 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?
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.
Sep 29 2025, 02:13 PM

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