Repeating karmic patterns across multiple lifetimes is a common
theme (analogy : if you have not yet achieved a satisfactory grade
in a particular exam / module / course / issue, you would want
to repeat it for the sake of personal growth and gain, even if
you're in a different lifetime / school / company / organization in
different time periods).
It would not be surprising if, in a past life in the medieval or
renaissance or the roaring twenties (or any other time period in
any country) era, he was similarly the son of a fairly wealthy
upper middle class baron or businessman, while she was a
princess of sorts, possibly royalty or at least much richer and
more powerful than his family was.
He may have, similarly to today, pined for her
superior-class hand in marriage with futility. Such
strong emotions, generated over many years of anguish
and psychological torment, leaves a strong psychic and karmic
footprint, an unresolved issue the soul must continue to
work with and balance, in future lifetimes.
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Confession: I live in a semi-D and drive a car but I'm still not
good enough for her
http://singaporeseen.stomp.com.sg/stomp/sgseen/editorpick/1827302/im_not_poor_but_i_feel_inferior_to_my_rich_girlfriend.html

Today's confession features an NUS undergrad who is in love with
a girl from a rich family, and he feels inferior trying to woo her
although he himself is also quite well-to-do.
Here is the confession in full:
"I feel that my life mirrors that of Jay
Gatsby.
"The 'Daisy' I love is from Medicine faculty and she comes
from a family of bankers who have amassed their fortune for at
least 3 to 4 generations. Living at her Nassim Road bungalow, she
probably has everything she wants - smart, pretty, rich, with a
sophisticated lifestyle. Sometimes I catch her getting chauffeured
to school in a Bentley during the mornings I have my breakfast at
Starbucks. What a great start to my day!
"While I on the other hand live in a commonplace
semi-detached off Braddell Road. My father is a businessman, and
our family earned the money through my parents' hard work and are
the noveau riche. While I am aware that I am fortunate that I can
drive to school and live relatively comfortably, compared to my
"Daisy," it is still not enough for her.
"Before all of you label me as spoilt and insensitive, let me
just say that I know that I am very lucky to be in this financial
position. But I cannot help but feel inferior when the girl I am
trying to woo is living in her palatial home with everything she
can ever want.
"Bear in mind that I am just a simple arts student, and the
reason why she has not reciprocated my overtures is partly because
she is hesitant that I am not up to her standard. I have done
everything I can to prove my sincerity, and some of my friends say
that I should just find someone else.
"But I cannot help myself. "Daisy" is the world to me and I
even saved up my allowance to buy her a Dooney & Bourke handbag
because I know she likes collecting them.
"I feel like I am not good enough for her. She is across the
bay and I find that even though I stretch out my hands further, she
is still being non-committal about our
relationship.
"It is as though I have exhausted all my
options.
"What should I do?"