A real sample game

How well do you know Riley?

Thirty questions for Riley's 50th — guess loud, score loose, no prize money.

30 questions · ~10–15 minutes of play

1. Question 1 · easy

   How long has Riley been teaching middle-school science?

   • A. 25 years and counting ✓
   • B. 10 years
   • C. 5 years
   • D. Just started last fall

   Reveal: Yes — 25 years and counting at Coastal Middle.

2. Question 2 · easy

   What subject does Riley teach?

   • A. Middle-school science ✓
   • B. High-school maths
   • C. Elementary art
   • D. College philosophy

   Reveal: Riley has been teaching middle-school science the entire time.

3. Question 3 · medium

   Which school has been Riley's classroom for all those years?

   • A. Coastal Middle ✓
   • B. Riverside Elementary
   • C. Hilltop High
   • D. Lakeview Academy

   Reveal: Coastal Middle — same building, same parking spot, presumably.

4. Question 4 · easy

   What car has Riley refused to upgrade since 2004?

   • A. A green Camry ✓
   • B. A red pickup truck
   • C. A blue minivan
   • D. A black motorcycle

   Reveal: The green Camry has outlived three garage-door openers.

5. Question 5 · medium

   What year did Riley get the green Camry?

   • A. 2004 ✓
   • B. 2014
   • C. 1999
   • D. 2020

   Reveal: Owned since 2004 — that car has seen things.

6. Question 6 · easy

   What's Riley's stance on getting a newer car?

   • A. Refuses, the Camry stays ✓
   • B. Already ordered the new one
   • C. Trades cars every 3 years
   • D. Would only consider a different brand

   Reveal: Refuses every time. The Camry stays.

7. Question 7 · easy

   What year did Riley adopt Mango the cat?

   • A. 2019 ✓
   • B. 2009
   • C. 2024
   • D. 1999

   Reveal: 2019 — the cat is now an old colleague.

8. Question 8 · easy

   What colour is Mango the cat?

   • A. Orange ✓
   • B. Black
   • C. White with grey patches
   • D. Calico

   Reveal: Orange, in case the name didn't tip anyone off.

9. Question 9 · medium

   Where does Mango famously turn up most often?

   • A. In Zoom meetings ✓
   • B. On the kitchen counter
   • C. Sleeping in the dryer
   • D. At the front door

   Reveal: Mango sits in on Zoom meetings — sometimes contributes opinions.

10. Question 10 · easy

    What food argument does Riley always lose at family dinners?

    • A. Pineapple on pizza ✓
    • B. Mayo on fries
    • C. Ketchup on eggs
    • D. Mustard on hot dogs

    Reveal: Pineapple on pizza — Riley has never won this argument and never will.

11. Question 11 · medium

    How does the family describe Riley's record on the pineapple-pizza debate?

    • A. Loses every time ✓
    • B. Wins on technicalities
    • C. Refuses to engage
    • D. Switched sides last year

    Reveal: Famous in the family for losing every argument on this one.

12. Question 12 · medium

    What has Riley quietly run at the school since 2008?

    • A. The musical sound desk ✓
    • B. The cafeteria committee
    • C. The yearbook printing
    • D. The bus schedule

    Reveal: Sound desk for the school musical, every year since 2008.

13. Question 13 · hard

    What year did Riley start running the school musical sound desk?

    • A. 2008 ✓
    • B. 2018
    • C. 2000
    • D. Last spring

    Reveal: 2008 — and never asked to be on the program.

14. Question 14 · easy

    Which app does Riley flatly refuse to learn?

    • A. Snapchat ✓
    • B. Email
    • C. Voicemail
    • D. Solitaire

    Reveal: Snapchat — claims it gives him a headache.

15. Question 15 · medium

    What's Riley's stated reason for refusing to learn Snapchat?

    • A. Says it gives him a headache ✓
    • B. Says it eats too much battery
    • C. Says he doesn't have time
    • D. Says the icons are too small

    Reveal: He says it gives him a headache. The family has stopped trying.

16. Question 16 · medium

    Which mountain did Riley climb on his 45th birthday?

    • A. Kilimanjaro ✓
    • B. A local hill
    • C. A treadmill at the gym
    • D. Mount Snowdon

    Reveal: Kilimanjaro — and brought a cake.

17. Question 17 · medium

    What did Riley take to the summit of Kilimanjaro?

    • A. An actual cake ✓
    • B. A copy of the local paper
    • C. A pet rock
    • D. Three sandwiches

    Reveal: An actual cake. Documented. Photographed. Eaten.

18. Question 18 · hard

    Which birthday triggered Riley's Kilimanjaro climb?

    • A. His 45th ✓
    • B. His 30th
    • C. His 50th (this one!)
    • D. His 60th

    Reveal: 45th. So this 50th better be impressive.

19. Question 19 · medium

    What year did Riley and Pat get married?

    • A. 1998 ✓
    • B. 1988
    • C. 2008
    • D. 2015

    Reveal: 1998 — Riley still has the suit; it does not still fit.

20. Question 20 · easy

    Where did Riley and Pat first meet?

    • A. At a Halloween party ✓
    • B. On a long-haul flight
    • C. In a science class
    • D. At a wedding

    Reveal: A Halloween party. Both in costume.

21. Question 21 · hard

    What was the awkward coincidence at the Halloween party where they met?

    • A. Both dressed as the same character ✓
    • B. Both spilled the same drink
    • C. Both forgot their costume
    • D. Both arrived two hours late

    Reveal: Same character. Different stores. The relationship has not recovered.

22. Question 22 · medium

    What is Riley's strict rule for family weddings?

    • A. One Old Fashioned, no second ✓
    • B. No dancing on the parquet floor
    • C. Has to leave by 10pm sharp
    • D. Always sits at the kids' table

    Reveal: Exactly one Old Fashioned per family wedding. No second under any circumstances.

23. Question 23 · easy

    Which drink does Riley always order at family weddings?

    • A. An Old Fashioned ✓
    • B. A glass of milk
    • C. An espresso martini
    • D. A pint of lager

    Reveal: Old Fashioned, every time, exactly one.

24. Question 24 · medium

    What does Riley do if offered a second Old Fashioned?

    • A. Politely declines ✓
    • B. Drinks it but complains
    • C. Pours it for someone else
    • D. Walks out of the wedding

    Reveal: Polite, firm decline. Every wedding. No exceptions.

25. Question 25 · easy

    Which film does Riley quote at every family dinner?

    • A. The Princess Bride ✓
    • B. Top Gun
    • C. The Godfather
    • D. Star Wars

    Reveal: The Princess Bride — known dinner-table hazard.

26. Question 26 · medium

    How does the family describe Riley's habit of quoting The Princess Bride?

    • A. A known hazard at every dinner ✓
    • B. A rare and precious treat
    • C. Strictly limited to Christmas
    • D. Something he's recently stopped doing

    Reveal: A known hazard. Every dinner. The grandchildren have started anticipating the lines.

27. Question 27 · hard

    Which of these hobbies does Riley NOT do, based on what we know?

    • A. Refusing to upgrade his Camry
    • B. Running a school sound desk since 2008
    • C. Climbing mountains with cake
    • D. Daily updates on Snapchat ✓

    Reveal: Trick — Riley does the first three. Daily Snapchat is the one thing he refuses.

28. Question 28 · hard

    Roughly how old is Mango the cat at this 50th birthday?

    • A. About 7 ✓
    • B. About 1
    • C. About 15
    • D. About 20

    Reveal: Adopted in 2019, so about 7 in cat years where calendars apply.

29. Question 29 · hard

    What's the fastest way to lose an argument with Riley?

    • A. Bring up pineapple on pizza
    • B. Suggest he get a new car ✓
    • C. Ask him to set up Snapchat
    • D. Try to skip family dinner

    Reveal: Trick — Riley LOSES the pineapple-pizza argument every time, but he wins on the Camry.

30. Question 30 · medium

    If you wanted to make Riley happy at this party, what's the safest bet?

    • A. A cake, ideally portable ✓
    • B. A new phone with Snapchat installed
    • C. A modern hybrid sedan
    • D. A second Old Fashioned

    Reveal: Safe bet: a cake. Riley has a documented history of taking cake to mountain summits.