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Past determining my future

Should I try asking out a waitress who was nice to me but I don’t know her name nor her relationship status?
Sure, but be prepared for a no for a myriad of reasons that are nothing to do with you at all: she has a partner, she's happy being single, she's got no time, she's contractually not allowed to date customers, she's not hetero, she's had bad experiences, she doesn't data strangers, etc.

But why not? "You seem such a lovely person. Can I invite you for a coffee soon (or whatever it is you plan)?" If she says 'no', at least a nice person got a compliment, which is always a win. And you get to know it's no big deal to basically communicate "you seem nice, and I like being with nice people" which is hardly taboo, is it?
 
Sure, but be prepared for a no for a myriad of reasons that are nothing to do with you at all: she has a partner, she's happy being single, she's got no time, she's contractually not allowed to date customers, she's not hetero, she's had bad experiences, she doesn't data strangers, etc.

But why not? "You seem such a lovely person. Can I invite you for a coffee soon (or whatever it is you plan)?" If she says 'no', at least a nice person got a compliment, which is always a win. And you get to know it's no big deal to basically communicate "you seem nice, and I like being with nice people" which is hardly taboo, is it?
reminds me of a video that only added fuel to fire towards my resentment of that tradition and gender expectation.
 
Doesn't that depend on where you think you are right now,
and the direction toward which you want to go in the future?
 
Doesn't that depend on where you think you are right now,
and the direction toward which you want to go in the future?
My thoughts are “How can I make a relationship happen when I am socially isolated and years behind my peers?”
 
I still have fears about my age (36), lack of social connections, and if there are even still single women out there being factors against me ever having a relationship.
 
Even when I was 16, I wondered why the girls at school went crazy for the other guys but not me.
 
Even when I was 16, I wondered why the girls at school went crazy for the other guys but not me.
Sounds like an appropriate thing to consider.

How do your current thoughts differ from your adolescent ones
on that topic? If they do, in fact differ.
 
Watching a few videos on current issues with relationships, really shocked looks like blowback or Newtonian physics. every action has an equal opposite reaction. It may not just be you but all guys your age NT AND ND. times have changed rules have changed. falling birth rates indicator of this.
 
Sounds like an appropriate thing to consider.

How do your current thoughts differ from your adolescent ones
on that topic? If they do, in fact differ.
“How can I make things differently? Is it even possible? Do I have to become like my older brother?”
 
I think you will find ladies changing in the next few years as they watch their biological clocks slowly shut down. inflection point rapidly approaching. Just stop acting desperate start planning on how to get your act together.
I have a younger brother still single Think he has ADHD gave up years ago his job got him travelling the world. military and previously fixing installing phone systems in developing countries. Most eligible guy I've ever seen
complained for years about his inability to get a girlfriend retires in a few months. Either way the issue was always him. He had no expenses lodging was paid by his former employer. Owns own home few expenses, just complains.
 
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“How can I make things differently? Is it even possible? Do I have to become like my older brother?”
So you're saying you're pretty much still wondering the same things as you
were years ago.
 
No fault, just a combination of your personality and changing times which may reset in a few years. I had an uncle who married late, wife had been married previously more than once, they had a fifty year marriage. He and her both lived well into their nineties.
 
Either for not doing more or if I am being punished by destiny because I was mean to my younger brother. The latter thought does make me wonder why my older brother had girlfriends while he constantly terrorized me.
 

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