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  • Nora & Estelle

Would you rather.... Teacher Edition!

We asked eight teachers eight “would you rather” questions. Here are their responses and the final tally!


  1. Mrs. Kathryn Pelson, Mathematics

  2. Ms. Alessandra King, Mathematics

  3. Ms. Tiffany Reddinger, Chemistry

  4. Ms. Smith, Grade 10 Dean and English

  5. Mr. Lynch, Upper School Director and History

  6. Mr. Duan, Chemistry

  7. Mr. Kosegarten, English

  8. Mr. Westerberg, PE chair and swim coach

Question 1: Would you rather chaperone Flashback or Holiday Ball?

  1. Mrs. Pelson: “Holiday Ball. Even though I think everyone's probably more relaxed at Flashback, it's at the beginning of the year, so I wouldn't know my new students as well as I would in December.”

  2. Ms. King: “Do I really have to!?!? Please please please…”

  3. Ms. Reddinger: “Holiday Ball- everyone is so elegant. There is MUCH less grinding!”

  4. Ms. Smith “Well, I have to do both; but I prefer HB. Less sweaty!”

  5. Mr. Lynch “Holiday Ball. Flashback is always hot and smelly.”

  6. Mr. Duan: “Both since I enjoy seeing the students whom I just get to know and whom already know well getting both ‘flashy and classy’.”

  7. Mr. Kosegarten: “I am always keen to get into the holiday spirit- Holiday Ball!”

  8. Mr. Westerberg: “Holiday Ball please”

The final tally:

Holiday Ball: 6

Flashback: 0

Both: 1

Neither: 1

Question 2: Would you rather have access to the school’s free masseuse or have someone grade your tests for you?

  1. Mrs. Pelson: “​This is a tough one. Can't I have both?”

  2. Ms. King:“Somebody please grade my tests!!! Grading is not my favorite part of the teaching/learning process….A masseuse is rather appealing though…Could I split? Sometimes I grade my tests and some other time I get a massage? Seems fairer….”

  3. Ms. Reddinger: “Grade tests- I love teaching, but I despise grading!”

  4. Ms. Smith:“Grading. Easy.”

  5. Mr. Lynch:“Grade test; I hate people touching me!!”

  6. Mr. Duan:“I never tried the free school massage and would consider one. But as it sounds contradictory as it is, I ‘spoil’ myself and sooth my body/mind often through ‘rough and tumble’ outdoor activities, which could be very therapeutical…”

  7. Mr. Kosegarten: “The school has a free masseuse? I need to check my email more often.”

  8. Mr. Westerberg: “Masseuse”

The Final Tally:

Masseuse: 3

Tests: 3

Both: 2

Question 3: Would you rather have Fundies class every day or have to teach every period?

  1. Mrs. Pelson:​”FUN-dies!”

  2. Ms. King:““Teach every period – not even close! What question is this!?! I love doing math with my students!

  3. Ms. Reddinger: “Fundies!!!!! I’d get on the elliptical every day if I had time-”

  4. Ms. Smith:“Fundies!! If I could get a free workout from an all-star Holton PE teacher every day, that would be the dream.”

  5. Mr. Lynch: “Fundies, I would bore myself teaching every day”

  6. Mr. Duan:“Don’t know what it exactly means, but you know I love to ‘gossip’ to start the class, but those gossips have been getting back to (or serving for) Chemistry ultimately….”

  7. Mr. Kosegarten: “I would definitely pull a hammy in Fundies- teach every period.”

  8. Mr. Westerberg: “Fundies class every day! Greatest class on the face of the earth.”

The final tally:

Fundies: 5

Teaching: 3

Question 4: Would you rather always have your phone in your hand for the rest of your life or never be able to use a phone again?

  1. Mrs. Pelson: “​Another tough one, except I want neither! I guess because I have my kids and a big family, I'd need to have a phone in my hand for the rest of my life. (I would definitely opt to wear Apple watch for that.)”

  2. Ms. King:“Oh no, I need my hands, and having one always occupied by a phone all the time would be a problem….Plus soon there will be much cooler gadgets that can do more and faster than a humble phone, so I will have one of those instead;)”

  3. Ms. Reddinger: “Phone in my hand- Candy Crush and Words with Friends vs. my husband – those are my guilty pleasures!!!”

  4. Ms. Smith:“Never use it again! Also, the dream.”

  5. Mr. Lynch:“Tough one, no phone”

  6. Mr. Duan:“With my handy Super-0.05-G-phone :)”

  7. Mr. Kosegarten: “Great question- I think never have a phone. I would be less anxious, and when making plans with people, they would be well in advance and they couldn’t cancel on me at the last minute.”

  8. Mr. Westerberg:“Hmmmmmmmm – tough question – pros and cons to both – I would lean towards probably having it in my hand although would probably rather the latter.”

The final tally:

Phone in hand: 4

No phone: 4

Question 5: Would you rather have a swim lesson with Mr. Westerberg or play a round of golf with Ms. Treadwell?

  1. PELSON:“​Golf! (Sorry, Graham...)”

  2. Ms. King:“Why going for a walk on my own is not an option? I kind of like my own company… (nothing against Mr. W and Ms T. of course; I have swimmers’ ear and golf has never appealed to me; sorry, golf lovers)”

  3. Ms. Reddinger: “Play golf- I’m a great swimmer already but I don’t swim often- Black girl hair issues”

  4. Ms. Smith:“Swimming! Duh! (Sorry, Mrs. T)”

  5. Mr. Lynch:“Those are miserable choices;I’m a better swimmer than Westerberg :) and golf with Treadwell sounds so boring!! Golf with Treadwell, the better of two evils”

  6. Mr. Duan: “A swimming lesson most definitely…”

  7. Mr. Kosegarten: “Golf wins every time. Coach T. and I could rehash our JV hoops success also on the putting green!”

  8. Mr. Westerberg:“No brainer – play a round of golf with Ms. Treadwell and watch her lose!”

The final tally:

Golf: 5

Swimming: 2

Neither: 2

Question 6: Would you rather have free Starbucks for the rest of your life or free Netflix, Hulu and Prime subscriptions forever?

  1. Mrs. Pelson:“As much as I love my Starbucks, I am a math teacher and I know the better deal for me would be the Netflix, Hulu and Prime subscriptions. (Plus, I think I'm becoming more of a Pete's Coffee fan...)”

  2. Ms. King:“Free Starbucks forever! I would never have hours and hours on hand to watch stuff (and If I have, I would like to use most for reading), but there is always some time for a cuppa, especially if it is with a friend or a family member…”

  3. Ms. Reddinger: “Starbucks! Although I like Peet’s Coffee & Tea better! Vanilla lattes with whipped cream with tons of nutmeg and cinnamon!”

  4. Ms. Smith:“Definitely Starbucks. That would save me boatloads of money.”

  5. Mr. Lynch:“Easy, hate coffee – I chose free subscriptions”

  6. Mr. Duan:“None of them are my cup of ‘free tea’.”

  7. Mr. Kosegarten: “I am trying to make coffee at home now, so definitely the TV subscriptions. I’d be missing out on great programming like “Tiger King” too!”

  8. Mr. Westerberg:“Starbucks – not a movie watcher although I will say I have become more of one during the COVID quarantine!”

The final tally:

Starbucks: 4

Subscriptions: 3

Neither: 1

Question 7: Would you rather get away with lying every time or always know that someone is lying?

  1. PELSON:​”Wasn't there a movie about this...? I guess the latter, even though I think, at times, ignorance is bliss”.

  2. Ms. King: “Always know when somebody is lying – although generally it is already pretty clear most of the time, and most of the time, the lies are not even that interesting…”

  3. Ms. Reddinger: “Know when someone else is lying! I hate when I have to lie, and I despise being lied to!”

  4. Ms. Smith:“I think I know that someone is lying.”

  5. Mr. Lynch:“Always know someone is lying; 90% lying rate is still an A in my book!!”

  6. Mr. Duan: No repsonse

  7. Mr. Kosegarten: “I would know I was lying, most importantly, so I would prefer to know when others are lying.”

  8. Mr. Westerberg:“Wow – tough question – always know that someone is lying”

The final tally:

Get away with it: 0

Always know: 7

Neither: 1

Question 8: Would you serve detention with Mrs. Craig or fall during the procession of graduation?

  1. PELSON:​”A no brainer! Any time with Ms. Craig is the best!”

  2. Ms. King:“Serve detention of course – Ms. Craig is pretty friendly.”

  3. Ms. Reddinger: “Serve detention! Falling is THE WORST! I fell on the Billy Goat’s Trail- HOW HUMILIATING!”

  4. Ms. Smith:“DETENTION! Fun fact: I never got detention while I was a student at Holton and actually begged my senior year French teacher to give it to me so I could go before graduating. On our last Tuesday of senior year, I think our entire grade went to detention. For some reason that I can’t remember, I ended up not being able to actually attend, and Mrs. Craig let me out of it. So, in short, it has been a lifelong dream of mine to serve detention with Mrs. Craig!”

  5. Mr. Lynch:“Detention, there are a lot of people watching at Graduation!!”

  6. Mr. Duan:“Detention since it is less publicly shameful….”

  7. Mr. Kosegarten: “Ms. Craig is a very interesting lady, so if she would allow it, I would prefer to chat with her during detention.”

  8. Mr. Westerberg:“Well, again this is a no brainer – detention with Ms. Craig – she is my friend!”

The final tally:

Detention: 8

Fall on stage: 0

Author’s Note:

Estelle and I had a lot of fun organizing this! I especially loved hearing the memories associated with some of these questions! I will always fondly remember the Billy Goat Trail with Ms. Reddinger, and I seriously enjoyed learning about Ms. Smith’s hilarious experience with detention. And now I know who to organize tee times for when we get back to school! A special thanks to all the teachers who answered these questions with extreme wit. Reading all the responses makes me feel a little closer to everyone in these times of distress. We hope you enjoy, and most importantly, stay safe!

Lots of Love,

Estelle Monti and Nora Hemsley

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