I found this company newsletter for American-Associated Insurance Companies. It's called the "Ink-Link" and is dated October 1952.
The pumpkin pin-up pulchritude is a young lass of 20 named "Bonnie Masters" and was a secretary for one of the agency's Supervisors. It appears she stepped in in lieu of their previous Valentine Queen who now found herself betrothed and whisked away.
I couldn't resist Googling her and was sorry to find she had passed in 2011 at the age of 79.
The newsletter also contained a surprisingly detailed story of the origins of Halloween.
The page that continued the article also contained a humorous advice column for Bridegrooms and Brides that would not serve well these days.
I couldn't find any information on American-Associated Insurance Companies. There is an Associated Insurance Company that was founded in 1923 and is still in business, but I'm not sure if they are related.
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