151 Funny This or That Questions to Ask in 2023

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I was part of a corporate leadership program where employees were matched up with mentors at their first meeting. The meeting facilitator introduced a fun game that helped us connect and engage. It was an icebreaker consisting of funny this or that questions.

I think you will agree that this idea for an icebreaker was brilliant. Not only did we get to know each other better, but sharing a few moments of fun helped put us more at ease in working together when back at our desks.

Not only are this or that questions good for engaging with others, but they are also a great way to combat boredom. If you’re in a group and the conversation starts to wane, using this or that questions to re-engage can save the day. And you’ll be the hero that made it happen.

It’s a fact that people will find this or that questions funny as they share their answers one-on-one with each other or with a group. In this article, I’ll give you 151 this or that questions to ask in 2023 that may prompt thought-provoking conversations and tickle your funny bone

What Are This Or That Questions?

This or that questions prompt participants to make a choice. Sometimes they are called “either/or questions” or “a/b questions.” These types of questions invite participants to decide which choice they prefer.

For instance, if you’re asked, “Rain or snow?” you would answer not just which you prefer… but also elaborates on why you made the choice. What’s really fun is when you add some humor, as in, “I prefer snow because I love getting frostbite!”

Questions like these, especially with a funny twist, can foster happiness and be used to create games for icebreakers, conversation starters (especially on a first date!), and team-building exercises.

From my experience, I’ve shared and learned tidbits of information and fun facts while playing the game. The emotional benefits of experiencing fun and happiness are enormous.

Variations of the funny this or that questions game can include setting a time limit for answers; you could use a timer on your phone or an hourglass. You can also set some ground rules, like keeping the conversation clean or no holds barred. Between two people, you can simply ask two or three funny this or that questions.

In a group, you can pair up people and ask all participants the same question as they take turns sharing with each other. Then, ask for volunteers to share with the entire group.

Or you could bring a couple of participants at a time onstage to share their answers as part of a presentation or show. The best part is, you can use this or that questions in virtual meetings as well to engage employees, friends, or family members.

Whether you use funny this or that questions in a corporate setting, at a family reunion or on a date… you’ll find it’s a great way to start conversations and keep them going. So let’s get this party started, shall we?

For The Foodies!

1.    Free pizza or calorie-free pizza?
2.    Holiday dinner: turkey or ham? 
3.    Birthday cake or coconut pie? 
4.    Meatloaf: ketchup or no ketchup?
5.    Baked potato or sweet potato?
6.    Mustard or ketchup?
7.    Chicken or steak? 
8.    Salad dressing: ranch or honey mustard?
9.    Pizza with pineapple or pizza with anchovies? 
10.    City ham or country ham? 
11.    Corn on the cob or candy corn? 
12.    Sweet tea or unsweet tea? 
13.    Dark chocolate or milk chocolate?
14.    Coffee: iced or hot? 
15.    Bread: sourdough or pumpernickel? 
16.    Sweet milk or buttermilk? 

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Sharing a few moments of fun helped put us more at ease in working together when back at our desks.

17.    Cream & sugar or cream, no sugar? 
18.    Breakfast time: Bacon or sausage? 
19.    Grits: sugar and butter or salt & pepper? 
20.    Favorite dessert: cake or pie? 
21.    Cobbler: blueberry or peach? 
22.    Crispy French fries or crispy calamari? 
23.    Japanese food or Chinese food? 
24.    Free appetizer or free dessert? 
25.    No sugar or sugar rush? 
26.    Chocolate or vanilla? 
27.    Mayo or Miracle Whip? 
28.    Bread: white or wheat? 
29.    Hot dogs or hamburgers? 
30.    Olive Garden or Red Lobster? 
31.    Soda: Pepsi or Coke? 
32.    Drink black coffee or clean a litter box? 

The Great Outdoors

33.    Fire pit or fireplace? 
34.    Country road or city street? 
35.    At the beach: Bare feet or flip flops?
36.    Saltwater pool or sandy beach? 
37.    Midday or midnight? 
38.    Kayaking or canoeing? 
39.    City living or country living?
40.    Cruise: Bahamas or Canada? 
41.    Sledding or skiing? 
42.    Stormy weather: Thunder or lightning? 
43.    Pouring rain or warm sunshine? 
44.    Favorite season: summer or winter? 
45.    Turn on the light or stay in the dark? 
46.    Snow angels or sandcastles? 
47.    Shovel snow or rake leaves? 
48.    At a resort: water slide or hot tub? 
49.    Where to stay: tent or hotel?
50.    Watch the sunrise or watch the sunset?
51.    Vacation time: mountains or beach? 

Let’s Get Adventurous!

52.    Scuba diving or sky diving? 
53.    Zipline or bungee jump? 
54.    Roller coaster or white-water rapids? 
55.    Surfboard or skateboard? 
56.    You: life or the party or a wallflower? 
57.    Surprise party or planned party? 
58.    Pierce your ears or pierce your nose?
59.    To be or not to be? 
60.    Wear a cowboy hat or wear a motorcycle helmet?
61.    Singing karaoke or roller skating? 
62.    Go back in time or travel to the future? 
63.    Play baseball or watch baseball? 
64.    Read a book or write a novel?

Personal Preferences

65.    Money or brains? 
66.    A warm hug or a warm cuddle? 
67.    You or them: beard or mustache? 
68.    Make-up: eyeliner or lip liner? 
69.    Make-up or no make-up?
70.    Dyed hair or au naturale?
71.    Body wash or bar of soap?
72.    Chores: make the bed or fold the clothes? 
73.    Finding a date: looks or brains?
74.    Gifts: homemade or store-bought?
75.    Get a speeding ticket or walk 10 miles? 
76.    Go dancing or sing on stage? 
77.    Paperback book or e-book?
78.    Hair: dry it or air dry?
79.    Gym rat or couch potato?
80.    Christmas holiday: Live tree or artificial tree? 
81.    Getting cozy: A warm blanket or a cup of hot cocoa?
82.    Catch chicken pox or catch poison ivy? 
83.    Eat to live or live to eat? 
84.    Clown or magician?

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The emotional benefits of experiencing fun and happiness are enormous.

85.    Games: Bingo or Poker?
86.    Wash dishes or dry dishes? 
87.    Call or text? 
88.    Plan date night or wing date night? 
89.    Magic wand or genie in a lamp?
90.    Win the lottery or get married? 
91.    Physical calendar or digital calendar? 
92.    The workday: Work from home or work in the office? 
93.    Hoarder or minimalist?
94.    Write with a pen or write with a pencil?
95.    Paper money or debit card? 
96.    Short hair or long hair? 
97.    Tanning bed or tan in the sun? 
98.    Get a roomie or live alone?
99.    Hop a train or hop an airplane?
100.    Video games or board games?
101.    Live on the east coast or live on the west coast?
102.    iPhone or Android phone?
103.    Reading a good book or watching a good TV program?
104.    Listening to soft music or rockin’ out to loud music?

On the ‘Net and TV

105.    Twitter or Facebook?
106.    Family Feud or Jeopardy?
107.    Comedy or drama?
108.    Steve Martin or Stephen King?
109.    Watching sports: football or basketball?
110.    American Idol or America’s Got Talent?
111.    Shopping: Amazon or eBay?
112.    Star Trek: Captain Kirk or Captain Picard?
113.    TikTok famous or Insta famous?
114.    Tennis or pickleball?
115.    Wheel of Fortune or Price is Right?
116.    Netflix or Disney+?
117.    No TV or no cell phone? 
118.    Movie or theater play?
119.    Father of the Bride or Bride of Frankenstein?
120.    Sitcom or stand-up?
121.    Nonfiction or fiction?
122.    Serious or Silly?

Animal Stuff

123.    Rabbits or squirrels?
124.    Dogs: Poodles or Pugs?
125.    Circus or Cirque de Soleil?
126.    Dinosaurs: T-rex or Triceratops?
127.    Horses or horsing around?
128.    Hummingbirds or peacocks?
129.    The 3 Little Pigs or Peppa Pig?
130.    Dog person or cat person?
131.    Goldfish in your aquarium or Koi in your pond?
132.    Mickey Mouse or Minnie Mouse?
133.    Visit the zoo or ride the rides at a carnival?
134.    A dinosaur’s roar or a cat’s meow?

Fun Stuff

135.    It's the weekend! Saturday or Sunday?
136.    Silly putty or playdough?
137.    Sirius or FM radio?
138.    Shopping or delivery?
139.    Get up early in the morning or stay up late at night?
140.    High heels or sneakers?
141.    Morning person or night owl?
142.    Ride the bus or walk on the sidewalk?
143.    Rich in money or rich in knowledge?

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If you’re in a group and the conversation starts to wane, using this or that questions to re-engage can save the day. And you’ll be the hero that made it happen.

144.    Win the lottery or win his/her heart?
145.    Never shave or never get a haircut?
146.    Love or like a lot?
147.    One good day in a week or one good week in a month?
148.    Sneezes or hiccups?
149.    The color blue or the color pink?
150.    Elvis Presley or Sir Elton John?
151.    Ghastly Ghosts or evil zombies?

Final Thoughts on Funny This or That Questions

There’s no doubt that people will find this or that questions funny as they engage and are entertained by each other’s answers. The more outrageous the answers, the funnier they are, and the more participants will enjoy the exercise.

Consider using this list when you’re planning your next holiday party or family get-together. And you may want to tuck a few away for the next time you’re on a date. After all, wouldn’t you want to wow your dinner guest with your conversational skills?

The good news is that our list is divided into categories, making it easy to pick just what topic you want when choosing questions. This or that questions are some of the best icebreakers and conversation starters you’ll find.

They not only start the conversation, but they keep it going as one question leads to an answer that can then lead to an entire conversation. Before you know it, you have gotten to know the participants in the game, and they’ve gotten to know you a bit better.

When you use this or that questions in any setting, you’ll find it opens the door to conversations among group participants and one-on-one encounters. Good conversation is important in cultivating relationships, whether they are personal or professional.

On a professional level, conversation skills can help in several areas.

  • In a job interview, speaking well matters whether you’re the interviewer or interviewee.
  • Working alongside other employees, how you engage in your day-to-day matters and can lead to making your workday more enjoyable as you connect with your coworkers.
  • With other businesspeople, in networking groups, conversation matters.

On a personal level, this or that questions can bring you closer to those you love. Best of all, playing the game or just asking this or that questions one-on-one can be fun for your entire family, from young to old.

And there are more ways to use the game for fun and engagement. To have some fun with your significant other, here’s a list of this or that questions just for couples.

What a great way to engage with your loved one! You may find this to be an excellent pastime for years to come… and increase the overall happiness in your personal relationship. Let’s not forget the most beneficial angle…scientific research reveals that happiness is good for us. Both laughter and humor can be therapeutic.

Laughter actually lights up multiple areas in our brains, giving us doses of dopamine to feel good and serotonin to lighten our mood. When you share funny this or that questions, you’ll not only tickle your funny bone… but you will also go a long way toward keeping yourself and those with whom you engage happy and healthy.

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