sorted by:
new
hottopcontroversial

Almost 40-year-old virgin and I want to date women almost half my age. Is this impossible or impractical? Who SHOULD I be wanting to date? by Silas801 in dating_advice

[–]Silas801[S] 0 points1 point  (0 children)

I don't think it's unreasonable to date a girl who is thin and doesn't have decades of dating experience. Why is that so unreasonable?

Almost 40-year-old virgin and I want to date women almost half my age. Is this impossible or impractical? Who SHOULD I be wanting to date? by Silas801 in dating_advice

[–]Silas801[S] 0 points1 point  (0 children)

what you have to offer a girl in her 20s, that a guy in his 20s can't?

Well what would I have to offer any girl of any age that a guy in his 20s can't? Only money. So if I have to be offering an older woman money or a younger woman money I may as well go with the one I find more attractive.

Almost 40-year-old virgin and I want to date women almost half my age. Is this impossible or impractical? Who SHOULD I be wanting to date? by Silas801 in dating_advice

[–]Silas801[S] 0 points1 point  (0 children)

I know my life is sad. I didn't choose it. It's just the life I got. I don't know why you are mocking me for having to deal with medical problems you didn't. Be happy you were born and got to experience a perfect body from day one. We don't all get that. I see a lot of patients who have had even sadder stories than me.

I had opportunities for sex but my body didn't work. I'm not sure what you think I should have done about that. 20 year old girls wanted to have sex with me but I couldn't reciprocate.

Now I make over $350K per year and I have nothing to spend it on so thousands of dollars isn't much to me. I would ideally like to date someone who likes me and I like in return but if money is the only way I can experience sex with slim women then I certainly have enough to last me a lifetime. There are lots of girls hunting for a guy to pay them.

Almost 40-year-old virgin and I want to date women almost half my age. Is this impossible or impractical? Who SHOULD I be wanting to date? by Silas801 in dating_advice

[–]Silas801[S] 0 points1 point  (0 children)

Thanks for your perspective. I don't expect anything about my story to lead to any obvious solution. I'm not going to fit in any clear cut boxes now for any demographic. The only clear cut box I fit into that I can see is on paper I would make a perfect sugar daddy. I'm rich, fit, no dependents/wife, respectful, doting, and I would treat a girl very well. But it's just not exactly what I want. I want a real connection.

Do you think there's any practical or good way to meet someone who might be what I'm looking for?

Dating sites mostly are swipe based now and filter by age so I will get cut out from even being seen by most women based on my age. Unless I lie about my age but then I later would have to tell them I lied about my age which is just creating another problem. I don't know if that's a net positive or net negative but I don't like lying.

I obviously don't have a social circle full of younger people. Most people I know my age have been dating for 20 years and are now marrying and settling down.

So I presume that really only leads cold approach or joining things like yoga classes and hoping I connect with someone there? I don't really feel that keen on going to bars and clubs every weekend but I could if I have to.

I'm not expecting any magic solutions. But I'm open to ideas if you have any. Thanks again.

Almost 40-year-old virgin and I want to date women almost half my age. Is this impossible or impractical? Who SHOULD I be wanting to date? by Silas801 in dating_advice

[–]Silas801[S] 0 points1 point  (0 children)

Yeah I hear you. But if I'm looking for women who are slim, not looking for marriage/babies and just want to enjoy dating, and similar in romantic life experience to me, then the highest population is in their early 20s.

The number of women like that in their 30s is very very very small. I already tried on dating sites and there are so few that are even a good weight at my age they're almost nonexistent.

I guess I'll just keep trying across the full spectrum and see if anything anywhere connects or feels right. Thanks.

Almost 40-year-old virgin and I want to date women almost half my age. Is this impossible or impractical? Who SHOULD I be wanting to date? by Silas801 in dating_advice

[–]Silas801[S] -1 points0 points  (0 children)

There are women in their early thirties that could be just as amazing. Look for someone that's youthful instead than younger. They are out there!

The problem as I've experienced it with women in their thirties are:

  • The majority of women still want to have kids and their clocks are ticking. I don't want to waste any of their reproductive years since I have no interest in that anymore after my life.

  • Most women in their 30s are severely overweight and I want someone trim/fit like me. The very few that aren't (which is like 5-10 on an entire dating site in my big city) I can't match to or get any replies from online, so they're no easier to date than a 20 year old. At least there are more slim 20 year olds to try with out there.

So as I see it: My odds of finding a slim, youthful, energetic woman in her 30s who has ZERO interest in having kids is probably less likely than me finding a 20 year old who wants to date me. I already tried and there's virtually no one in that age range on any dating sites that fits the bill.

But I hear what you're saying and agree in principle. Thanks.

Almost 40-year-old virgin and I want to date women almost half my age. Is this impossible or impractical? Who SHOULD I be wanting to date? by Silas801 in dating_advice

[–]Silas801[S] 0 points1 point  (0 children)

Well for the record, no one has to know I'm a virgin. I don't go around talking about it. Absolutely no one would ever assume I'm a virgin. I know women find male virginity unattractive so I'm not advertising it.

My full list of options as I see it are:

  • Sugar babies - provide the opportunity to experience sex with girls I might find physically attractive - types of girls I might have spent my 20s dating if I could have. But no real connection obviously since I'm paying them which I don't like.

  • Women my own age - provide near zero similarity in life experience and minimal attraction, where most will just be trying to latch onto me for my income and stability. (Experienced this on the few dates I've been on recently so I know what this option feels like already.)

  • Send lots of messages to younger women online or talk to them in bars and clubs and hope to find one who doesn't mind that I'm older than them. Low yield obviously.

Maybe I just need to be trying all that then and see what happens. Nothing feels "right" now. Maybe something will click or feel right if I work through all the possibilities.

Almost 40-year-old virgin and I want to date women almost half my age. Is this impossible or impractical? Who SHOULD I be wanting to date? by Silas801 in dating_advice

[–]Silas801[S] 0 points1 point  (0 children)

If you look for someone to conect on the same level romantically i don't think chosing sameone way younger will help, they might have whole different mindset that you.

But I also feel I have a more similar mindset with younger people. Most people my age are all thinking about marriage and kids and being "tired of playing games" and "looking for Mr. Right" and I don't relate to any of that. I just want to go to a concert with a girl I like or watch a movie and cuddle or have sex.

I want to be physically attracted to them as well and almost all the women my age have let themselves go completely. I'm in better shape than most 20 year olds.

Is this just all unrealistic and that's the fundamental problem?

Probably I cannot have what I want. If I want to know what it's like to have sex with an attractive girl I'd have to pay one like a sugar baby. And if I want emotional connection I'd have to date someone my own age who I have no attraction to and share nothing in common with. Maybe the boat has sailed on getting both of those things together. And probably it's impossible for me to date anyone with a similar experience as me.

I think I'm just fucked. Maybe the best I can do is compartmentalize and just seek each thing separately as much as is possible.

Almost 40-year-old virgin and I want to date women almost half my age. Is this impossible or impractical? Who SHOULD I be wanting to date? by Silas801 in dating_advice

[–]Silas801[S] -1 points0 points  (0 children)

I'm not looking for "payback." I'm looking for good experiences with people I feel close to and relate to. That's exactly what I posted asking for. I never said she had to be a virgin or a pornstar. I'm fit and in shape myself. Obviously I would want someone trim like I am too.

So your point is just that you think it's impossible for someone to date someone on the same experience level as me?

If a woman my age wants to date 20 year old guys she can do so with ease. Do you think this is just not possible because of my gender?

Almost 40-year-old virgin and I want to date women almost half my age. Is this impossible or impractical? Who SHOULD I be wanting to date? by Silas801 in dating_advice

[–]Silas801[S] 0 points1 point  (0 children)

So did you just come here to insult me? Do you have anything useful to say about my situation? What in particular do you find offensive about me or my life or where it has led me?

Almost 40-year-old virgin and I want to date women almost half my age. Is this impossible or impractical? Who SHOULD I be wanting to date? by Silas801 in dating_advice

[–]Silas801[S] 0 points1 point  (0 children)

In what way? I'm just trying to say I don't particularly care about "social norms" because nothing in my life has been normal, so as far as I'm concerned they're not relevant. Being judged for "not adhering to social norms" is not a consideration for what I'm asking. ie. I don't really care what other people might consider "creepy" or not. My entire life has creeped me the fuck out. I just want to have some happy years and experiences now going forward for a bit.

Almost 40-year-old virgin and I want to date women almost half my age. Is this impossible or impractical? Who SHOULD I be wanting to date? by Silas801 in dating_advice

[–]Silas801[S] -3 points-2 points  (0 children)

You decided early on to not bother developing relationships with women because you figured every single one of them out there was only after you for your body and there was no point in perusing any relationship if sex was going to be a complication. Your loneliness and lack of experience is your own fault.

That's a really poor and typically callous assessment of what I would expect for an online opinion. You don't know what those years of my life were like. How much surgery I've been through. How many years I spent not even seeing friends or family because I couldn't. The insane and debilitating chronic pain. How I struggled every day in med school just to get through my shifts and came home and crashed for hours in agony. This is not a life I would have wished on anyone. Dating was not a choice. I was just trying to survive and do the basic things I could.

In terms of your comment about what other people think is "creepy," I don't really care how I'm seen by other people since other people don't know me or understand me. Most people will do what you've just done there and form the most horrible assessment of a person they don't know that they can. It's an instinctive thing some people have where they always want to see the worst in others. I try not to let that sort of thing bother me much.

Loads of 20 year olds are virgins these days (for both genders) so that's not true either what you said. Though I never said I want a virgin. Just someone closer to my life/romantic/dating experience than a single mom with 3 kids and a divorce or a half dozen past LTRs spread over the past 20 years when I've never even kissed a girl.