PUBERTY
Shirt and Socks
Jack-Assery
The Big O
Jacktivities
100

Jack has never played this sport competitively, yet is frequently asked if he does. 

What is basketball?

100

Despite its outlandish price tag, more than 70% of Jack's wardrobe is from this retailer

What is Lululemon?

100

The name of this (should be illegal) substance that Jack and Olivia require all visitors to try in Chicago. 

What is Malort?

100

Olivia's job is this

What is a teacher?

100

This is the sport that Jack competed in during college

What is rowing?

200

Other than THE Milwaukee Bucks, Jack's favorite basketball team as a teenager was: 

a. Miami Heat

b. Golden State Warriors

c. Denver Nuggets

d. LA Clippers

Who are the LA Clippers/Lob City?

200

We know what they say about big feet... but Jack's actual shoe size is this

What is 13?

200

Jack and Olivia's go-to adventure is this. 

What is a cruise?

200
Olivia asked Jack out on this iPhone application (someone revoke his man card)

What is Instagram?

200

During high school, Jack helped after school to do this task for the arts/drama program.

What is building stage sets/props/crew?

300

During Cole's 5-man senior promposal, Jack painted this letter/character on his chest to spell out P-R-O-M-?

What is the letter O?

300

Jack is known to drink all alcohol, EXCEPT for this beverage. 

What is an IPA?

300

Jack almost died in this Central American country during COVID.

Where is Costa Rica?

300

One Christmas, Olivia covered Jack's room in this substance. 

What is wrapping paper?

300

Every weekend, Jack had to help out around the house and had limited social availability due to this chore.

What is mowing the lawn/yardwork/mulching?

400

During high school, Jack's guilty pleasure song on the radio was:

a. Fight Song - Rachel Platten

b. Call Me Maybe - Carly Rae Jepsen

c. All About That Bass - Meghan Trainor

d. Blank Space - Taylor Swift

What is Fight Song - Rachel Platten?

400

Jack's birthday is...

When is September 8th (1998)?

400

Jack's first job was this. 

What is a caddy?

400

Jack proposed to Olivia in this type of facility.

What is a greenhouse/garden?

400

This is Jack's board game of choice

What is Catan?

500

As a young child Jack was obsessed with this cartoon TV character.

Who is Bob the Builder?

500

Jack is a proud owner of this man's jersey despite only playing 3 years in the NFL (2010-2013) none with the Packers).

Who is Tim Tebow?

500

The Viking who Jack inexplicably drafted in the FIRST round of fantasy football in 2013 was: 

a. Adrian Peterson

b. Percy Harvin

c. Cordarelle Patterson

d. Greg Jennings

Who is Greg Jennings?

500

Every year, Jack and Olivia battle over which side of this trophy gets to be face up on their mantle.

What is Paul Bunyan's Axe?

500

Jack featured in this male vocalist's Instagram video during Summerfest and also met him on a flight. 

Who is Andy Grammer?