New here.

I thought I was the oldest person feeling anxious about asking a
girl out until recently, when I remembered a guy I once met in his
late fifties: who once told me that he has had to deal with shyness
all his life. And he'd *never* found courage to ask a girl out (has
friends but never had a girlfriend).
I also recall him telling me that loneliness is the worst part of
being alone; not having anyone to share life with. Like me he has
friends but no one special.
He told me to hurry and find someone so I don't end up like him.

When I examine at my life now I often wonder if I saw my future in
that man. I can relate very well how difficult it is not being able
to ask someone out; to not know how or when to ask.
What if the words I use are all wrong?
Will the other person reject me in a way that will hurt me (I don't
mind rejection unless it hurts)?

Even when it's appears very easy to ask, I can't help but get
anxious about how to ask the right way, and what could go wrong once
I do go out with the other person.
What if she lies by saying yes, but does show up because she
suddenly decides that since I didn't ask properly she thinks I'm no
good?

Tony