The Herman Files
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Guess Who?
100
What is Herman's middle name?
Joseph
100
What fictional spokesperson has represented Progressive Insurance since 2008?
Flo
100
What is the Dold drink?
Bourbon and wink
100
Name the traditional Christmas eve dinner at the Dold house.
Beef stroganoff, rice and salad. Colored pears as garnish.
100
What does “smh” stand for in texting and online slang?
Shaking my head
100
Who drank up all of the extra adult beverages at a Dold party as a toddler and fell down?
Elaine
200
Name 2 items that were typically on the table next to Herman's recliner.
Pipe, tobacco, lemon drops
200
What rapper is famously best friends with Martha Stewart?
Snoop Dogg
200
There are many family members that have the same birthday. Name at least one pair. Bonus for more named.
Melissa and Lisa, Anne and Sadie, Jen and Cyn
200
What was the traditional thing to do after dinner and before opening up presents on Christmas Eve?
Some of the adults would drive the kids around to look at Christmas lights while dinner was cleaned up.
200
Who has attended University of Michigan?
Kyle and Leslie
200
Which three actors named Chris have all played major roles in Marvel films?
Chris Hemsworth, Chris Evans, Chris Pratt
200
Who made it the NCAA in the Elite 8?
Bob and Jack
300
Name the great great grandchildren of Herman and Bobbie Dold.
Eva de Caussin & .....?
300
What 2020 documentary had us all watching the bizarre world of big cat breeding?
Tiger King
300
Name at least 5 different states where family members live and are here at this reunion?
California, Washington, Nevada, Texas, Maryland, Vermont, Massachusetts, Connecticut, New York
300
Name the song the Melissa, Lisa and Anne sang over and over and over again at Christmas.
Must be Santa
300
Name at least 3 people who have attended St. Mary's College from the family.
Jack, Nancy, Anne, Bob
300
Which social media app is still dominating short-form video in 2025?
TikTok
300
Who worked with Matthew McConaughey?
Alex
400
Name 2 different streets that Herman and Bobbie Dold lived on
El Dorado Avenue, Oakland
Scotia Avenue, Oakland
Valley West Circle, Napa
400
What day is celebrated as National Star Wars Day?
May 4th
400
Name 5 family members that live in Washington State.
Gini
Jen, Dave, Colin, Sadie
Cyn, Mark, Gus, Violet
Melissa, Kyle, Harper, Calla
400
What year did the Dold Family spend Christmas in Plymouth, MA?
1981
400
Name 2 family members who went to college in a different country OR who worked in a different country
Haroun, Michelle, Natalie, Alex, Lisa
400
What person has the most followers across all major social media platforms as of 2025?
Cristiano Ronaldo, with 816.1 million total followers across Instagram, Twitter/X, and YouTube
400
Who was an actor/extra on a shows called Marker, Maneater and After Armageddon on the History Channel?
Erik
500
Where did Herman and Bobbie meet?
Prison
500
What is the most watched YouTube video of all time?
Baby Shark Dance
500
What was the name of a great white shark spotted at the Jersey Shore in 2025?
Dold - named after Christopher Dold of SeaWorld, a key figure in ocean conservation, OCEARCH said. (not our Christopher Dold)
500
Name at least 3 family members that are or were teachers.
Too many to list
Gail, Bob, Jack, Dave, Gini, Lisa, Anne, Melissa, Kyle, Cheryl, Elaine, Holly, Natalie
500
Who holds the record for winning the most Oscars?
Walt Disney (22 oscars)
500
Who exchange puzzles back and forth and have been doing so for many years?
Ella, Gail, and Mary
600
Where was Herman born and on what day?
In Epiphany, South Dakota on Epiphany, January 6, 1906.
600
Name 5 actors that have been Batman on screen.
11 in total - Robert Pattinson, Ben Affleck, Christian Bale, George Clooney, Val Kilmer, Michael Keaton, Adam West, Robert Lowery, Lewis G. Wilson, Iain Glen, and David Mazouz.
600
Which collectible monster-shaped toy, designed by Hong Kong designer Kasing Lung, exploded in popularity on social media in 2025?
Labubu
