Food
Career
Sports
Family
Cape Cod
100

Hailing from the citrus family, this fruit is plentiful on the side of Jim's typical fish and chips order

What are lemons?

100

This is Jim's assistant that is stationed adjacent to his office

Who is Dawn Nunally?

100

This player wore #29 for the Celtics, and has seen Jim's feet

Who is Hank Finkle?

100

This niece is a hardcore republican, and is currently serving as a nurse

Who is Meg?

100

This is the town Jim currently resides in

What is Brewster?

200

Jim often uses the restroom when dining out, but he gives it this peculiar name

What is the little boy's room?
200

Jim has had many careers, but was this position at King Phillip High School

What is history teacher/coach?

200

Often referred to as the GOAT by Jim

Who is Larry Bird?

200

This niece currently attends college in Boston, and can often be seen with a vape device

Who is Jen?

200

This restaurant has been a family favorite for over 5 years, with their plentiful supply of lemons

What is the Weatherdeck?

300

This Italian favorite is commonplace on Jim's typical pizza order

What is sausage?

300

The name Jim wore on his nametag behind the bar

What is Orlando?

300

Jim led the King Phillip girls softball to this spot in the ranking of "Top 10 Hock Team of the 2010's"

What is #7?

300

This brother of Jim's is a reliable source of information for sports draft classes

Who is John?

300

This SWF staff member is the most annoying and obnoxious person on Earth

Who is Michele?

400

This is the fruit Jim refers to when he is hiding something rather unhealthy in his mouth

What is an apple?
400

This is Jim's current position at Mansfield Schools

What is Special Education Director?

400

The sport that is played by Tom Brady

What is football?

400

This nephew of Jim's was recently stationed at UMass to become a doctor

Who is Nick?

400

This is the bike path traveled on by Jim

What is the Rail Trail?

500

This type of cookie is Jim's newfound favorite, often being brought home in a brown bag

What is oatmeal chocolate chip?

500

This was Jim's teenage summer job, often spent in the sand

What is lifeguard?

500

This female athlete was found as a locker room cancer in her days with King Phillip, with Jim facing her parents often

Who is Meg Rico?

500

This daughter of Jim's is a huge loser

Who is Jordan?

500
In October, Jim will take a trip down to the cape with his brothers, titled "_____'s Weekend"

What is Boy's Weekend?