Hermit, I think I'm a mix of your attitude and me still desiring someone in my life age age 50. I envy you I can understand some of what you're saying.
The difference between you and me though, is that I started WAY late and didn't have my first...I guess relationship with a woman I met online and dated for 4 months. I was 27, she was 19. She was in college, I was in the workforce. Her mother didn't like our age diff as she thought it would be a distraction with her daughter's studies (which her parents were paying for...tuition, etc)
So she kind of was an influence on her daughter to end things with me. Turns out I was a rebound from a guy she had a hard time getting over.
Fast forward to my mid to late 30s, I didn't have any kind of relationship or intimacy with a woman until my mid, to, late 30s. She was a Christian gal, but wanted to do friends with benefits only, and I wanted to date her...she didn't want that.
Fast forward to my mid-40s and I had a real relationship with a lady I met, but it didn't last because she had a lot of emotional issues. A couple of years after her, I met what I thought would be the IDEAL girlfriend. She lived very local, no kids ( I didn't have any). I am a big cuddler, we loved cuddling. I couldn't get enough of it. We kept it light though. Then she revealed that she did want kids in her life, even if it's meant to foster....and it was a no-go for me.
Basically, I had such LONG gaps between relationships....the gaps were so long, the relationships so short-lived...I never experienced a LONG term relationship.
I think she's long gaps between relationships has kept me a bit starved for companionship...even at age 50, but what I read about you, you make some valid points. I'm figuring maybe I should immerse myself more in my geeky hobbies. I am big on board gaming with other people...so I MAY meet someone that way, but not counting on it.
Going to sci-fi conventions at admiring all that is there, including the pretty ladies in cosplay.
Now that I've turned 50 I am wondering if I should watch who I talk to as to not appear like some creepy old man making eyes at a lady, at least from their perspective. When I was 40, I didn't have that "I may or may not be a creepy old man" feeling, to now entering THAT realm. lol
I made a dear friend recently, very sweet, very nice smile....but we realized we had nothing in common, but our friendship is still intact. I remember her telling me about a guy that she befriended that tried to cross a boundary into romance, and she wouldn't have any of it. He went another direction.
I tend to befriend women, make them laugh and make them comfortable, but when I ask one out..it's like...they are taken aback or caught off guard....as if they were surprised I even asked. I often wonder if the Universe is not allowing me to have a companion in a romantic sense. It's like women look at me, and think I don't deserve it.
I don't really 'flirt" persee, as my conversations are more benign. I sometimes even try to avoid flirty banter at times, as to not come off as creepy.
The women who DID date me, and would let me be intimate with them...they actually said they dont' care about looks...that was my only ace in the hole.
When I actually do get girlfriend...it's like...I'm dreaming. It's like, I felt like I was dreaming....and it doesn't feel real sometimes. I think I've gotten a little bit better about not feeling that way with the recent relationships though.
ANyways, I ramble....I feel ya man.