Charles Van Doren has finally written about his involvement in the quiz-show scandal of the late 1950s. But this challenge concerns the first person he beat on Twenty One, Herb Stempel.
On what date did Herb's paternal grandparents marry, and did his grandfather wear a hat on that day?

No one ever responded to this one? I didn't solve it either, but let me post the things I found in case it helps someone else get closer. As to the hat question, the family contained hat makers and they spoke Yiddish, so I would think they might have worn hats.
Herb Stempel
On what date did his paternal grandparents marry?
Did his grandfather wear a hat that day?
b: 19 Dec 1926 in Bronx, NY
m: Toby Stempel (deceased)
m: Ethel Stempel
children: Harvey Stempel
1930 Bronx District 929, Bronx, NY Census
1495 11 357 Stempel, Dave head m w 32 m 22 Austria Austria Austria mfg men's hats 1913 yiddish NA
, Fanny f w 28 m 18 Russia Russia 1908 Yiddish A1
, Irvin son m w 9 s NY Austria Russia
, Herbert son m w 6 s NY Austria Russia
, Pearl dau f w 3 s NY Austria Russia
US WWII Army Enlistment Record
Name: Herbert M Stempel
b: 1926, white New York, NY
Enlistment: 10 Jan 1946 Brooklyn NY
Transporation Corps
Private First Class
One Year Enlisment
1 year of college
Civil Occupation: Postal Clerk or photographer, aerial ....
Single with dependents
1920 New York City New York Census
333 69 402 Stempel, Morris head m w 53 m immig. 1912 PA Austria Yiddish, Austria, Austria, Tinsmith shop
, Sarah wife f w 52 m 1912 PA? Austria yiddish
, David son m w 23 s 1912 Al Austria yiddish hatmaker factory
, Nathan son m w 21 s 1912 Al Austria yiddish hatmaker factory
, Virginia dau f w 19 s 1912 al Austria yiddish hatliner factory
, Sylvia dau f w 15 s 1912 al Austria german
California Death Index
David Stempel
SS# 140146485
male
b: 27 Sep 1897
pob: Austria
dod: 20 May 1966 in Los Angeles
Mother's maiden name: Sipser
SS Death Index
Herbert Stempel
dob: 7 Dec 1923
dod: Feb 1993
NY
residence: napa california
SS Death Index
Herbert Stemple
dob: 19 Dec 1924
dod: 29 Jun 2007
Issued Ohio
residence: New Philadelphia, Tuscarawas, OH
I added both the above to warn folks to make sure they had the correct Herbert Stemple.
Sorry: right Herbert M. Stempel, wrong parents.
Herb gives some clues as to his heritage at the beginning of this interview.
Teresa got the answer.