Fortysomething Male here. I've had more lottery wins than I've had first dates!
In answer to your questions:
Why do you think you've ended up in this position? Is it by choice?
At school I was bullied constantly by a lot of people. Even those that weren't bullies just wouldn't even be associated with me 'cos that wouldn't be cool, much less date me!
I'm about 5'3, so online dating is like the first round of Guess Who - Anyone less than 6' gets eliminated in the first round - either because you ladies like a tall man to make you feel all protected & safe. Or because if you date a short man you feel silly in heels (Great, so now I can't get a date because of a pair of inanimate objects!!)
Now, according to various threads on MN, because I'm in my 40's, childless and with nothing to put on my dating CV - apparently that raises red flags and means I'm immature.
How do you feel about it?
Gutted!
Have you accepted it and truly stopped looking for love?
I wouldn't say accepted "it". But I've accepted that the odds are stacked against me, so yeah - I gave up looking a long time ago.
Or are you still hopeful?
Not really. I'd love it to happen! But I'm not going out of my way to look for it any more. And yes - I realise that limits my chances, but.. meh... Why keep flogging a dead horse! Better things to invest my time & energy on.
What are the positives to this lifestyle that you've found?
I can do what I like, when I like. And the money I saved not dating, getting married and having kids meant I could semi-retire early. (So I can spend more time playing with my Lego - y'know, being immature and all that! :P )
Do you think you can be truly happy if you never get the chance to experience a relationship?
I don't know. Grass is always greener, etc. I like the idea of being in a relationship. But then sometimes I look at friends relationships (and plenty of dramas played out here on MN) and wonder if it's really all it's hyped up to be or whether I am better off living my selfish single life!
Do you think that admitting to a date that you've never been in a relationship is such a huge red flag that they probably will run for the hills afterwards?
As mentioned above - I've seen enough posts here on MN where women have stated it's a red flag.
Bonus Question - From a bloke's POV, Do I see it as a red flag if a woman hasn't had a relationship?
Absolutely not! I would much rather date a lady who's not had a relationship than one who has had quite a few. I'll stick my head above the parapet and suggest that both men and women who have a substantial dating history are more likely to be the "life & soul of the party" aesthetics. Where as us terminally single are probably the more "plain Jane", curl up in front of the fire with some cocoa types - and that suits me! :)