101 This or That Questions – Thought-provoking conversation starters.
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Knowing a few good this or that questions is essential… because:
As most of you know, the purpose of a good question is to spark some interesting back and forth. That may seem obvious, but it’s actually pretty hard to find the right questions to ask to pull it off.
One kind of questions, though, always gets some intriguing discussion going: this or that questions.
When you make people make a choice, you make them really consider your question, and that makes the answers far better.
Use some of our great “this or that” questions below to make your conversation that much more interesting.
You can drop one in a second and then let everyone jump on the answers. Take a handful of these, and try them on your next set of conversation partners.
Here are 15 this or that conversation starters:
1. Bacon or sausage?
This question is, in fact, absolutely impossible to answer.
2. Chinese or Japanese food?
The foods are so different, and it says a lot about someone which they prefer.
3. Dogs or Cats?
Choose between the lovable companion or the cool, independent cuddler creature.
4. iOS or Android?
It’s the great issue of the 21st century.
5. Cake or Pie?
Remember, both is not an option.
6. Train or Plane?
Charm vs. convenience: which is more important?
7. Coffee or Tea?
In the battle of the great caffeine drinks, everyone has an opinion.
8. Beer or Wine?
Pick the people’s drink of choose or something a little more snobbish.
9. Soup or Sandwich?
So good together, but if you have to choose just one?
10. Card Game or Board Game?
Fun to discuss, and you can use the answer for get togethers later.
11. Dine In or Delivery?
Is the person a homebody or someone who likes to get out?
12. Motorcycle or Bicycle?
Who’s for adventure and who just likes a pleasant ride?
13. Book or eBook?
Books are so quaint and old-fashioned, but eBooks are just so convenient.
14. Ninjas or Pirates?
Everyone loves both, which makes it so hard to choose.
15. TV Shows or Movies?
Is it better to have an extended adventure or get it all in one sitting?
When you’re not just looking for an opener but for a question to change the whole dynamic of your conversation, that is when you want this list.
Pick and choose a few of these, and let your questions get everyone talking.
Here are the 14 best this or that questions:
16. Pop or Indie?
It all depends on what your definition of cool is.
17. What’s worse: Laundry or Dishes?
It’s a battle of the chores we all hate, but which is really the most excruciating?
18. Couch or Recliner?
Choose the best way to relax after a hard day.
19. International Vacation or a New TV?
Will it be adventure or something new?
20. Working Alone or Working in a Team?
A great one for colleagues or for after-work drinks.
21. Perfect teeth or perfect hair?
Which makes someone more attractive, and which can you get away without?
22. Arctic or the desert?
Two extremes that would be miserable, but it all comes down to cold vs. hot.
23. Forest or beach?
Both are secluded and relaxing, but you can only have one.
24. Theme park or water park?
Where can you really maximize your fun?
25. Africa or Asia?
Two continents most people would love to visit but never get around to.
26. Antique or brand new?
The charm of the old or the shininess of the new: you decide.
27. Mansion in the suburbs or cabin in the mountains?
Pick between glamor with everyone watching or confined but isolated.
28. City or country?
Where is it really best to live?
29. Charming or genuine?
What kind of person would you rather be with, or, which quality would be better?
Use these questions at unexpected moments to start the ball rolling with genuine first reactions. Those are always the most amusing.
Here are 16 funny this or that questions to ask:
30. Toilet paper: Over or Under?
Someone’s bound to scream others are doing it wrong.
31. Cups in the cupboard: Right Side Up or Up Side Down?
No question has ever been more important.
32. Wet or dry?
Just let everyone else figure out what situation you’re thinking of.
33. Smile or game face?
A chance to practice both.
34. Abs or chest?
Time to get everyone to compare torsos.
35. Lust or love?
Both is not an option, people.
36. Weird or normal?
Weird, obviously, or they wouldn’t be talking to you.
37. Elmo or Ernie?
People take their childhood favorites very seriously.
38. Slacker or over-achiever?
Just how is it better to go through life?
39. Truth or dare?
Everyone knows where this’ll lead.
40. Stop or go?
It all depends on what’s stopping and who’s going, right?
41. Hidden or discovered?
Are we playing hide and seek here?
42. Touch or taste?
Everyone will be left wondering what it would be like to be without either.
43. Younger or older?
Find out what first jumps to their minds with this choice.
44. Alone or in a crowd?
Everyone’s mind will go to exactly the wrong place.
45. Real or artificial?
It could be a philosophical question, or you may just be asking if the waiter’s got a toupee.
When you’re considering questions to ask a girl, you want something that makes her make a choice, so you can learn something about her while enjoying a talk.
These this or that questions are sure to keep her interested, and they have all sorts of great, sometimes romantic, directions they can take after you’ve asked one.
Here are 14 great this or that questions to ask a girl:
46. Call or Text?
An easy way to transition into getting her number.
47. Facebook or Twitter?
Social media choices say a lot about who we are.
48. While walking: Music or Podcasts?
An easy way to then ask for recommendations of either.
49. Swimming or Sunbathing?
You can find out how she likes to relax with this in the sun.
50. Big Party or Small Gathering?
A great way to gauge how social she is.
51. Skirt or pants?
The question is a weighty one for women.
52. Classical Art or Modern Art?
Show her your more cultured side.
53. Fast food or sit-down restaurant?
Is she no fuss or into a bit of romance?
54. Heels or flats?
Every girl has an opinion about this one.
55. Curly or straight?
Hopefully her choice matches your hair.
56. Spring or fall?
Find out what she associates with her favorite.
57. Online or at the mall?
How does she prefer her shopping?
58. Credit card or cash?
She’s sure to have an opinion one way or the other.
59. Sofa or loveseat?
Has a better question been invented to move her towards thoughts of sharing either with you?
Whether you’re looking for a casual chat, a new friend, a business partner, or a romantic partner, you needs questions to ask a guy just like you need them for a girl.
It’s a myth that guys are necessarily easier to talk to you. You need good questions to get them to open up just like with girls.
So use some of these, and you’ll get a conversation going in no time.
Here are 12 this or that questions to ask a guy:
60. Cardio or Weights?
If he works out, he’ll have a strong opinion about this.
61. Mobile Games or Console Games?
If he games, it’s just like the question above.
62. New Clothes or New Phone?
Is he fashion forward or Apple-product crazy? He can’t have both!
63. Football or Basketball?
Just get him started on sports and conversation takes care of itself.
64. Car or Truck?
Sleek cars or tough trucks, both have plenty of macho value.
65. Iced Coffee or Hot Coffee?
A little silly, but find out his reasons afterward.
66. Ocean or Mountains?
Where does he go to find the beauty of nature?
67. Straight or Mixed?
Does he take whiskey straight or does he drink Bloody Marys.
68. Brunette or blonde?
We all know we have a preference.
69. Boxers or briefs?
The age old question to ask every guy.
70. Long hair or short hair?
Another question to find out what he’s looking for in a partner.
71. Skydiving or bungee jumping?
Even if he’s afraid of heights, make him answer.
If you need questions to ask to get to know someone, the best thing you can do is give them a simple choice to make.
They may just be answering a little question about their preferences, but you’re learning a lot with every single question. Take a few of these with you the next time you’re out meeting people.
Here are 15 or that questions to get to know someone:
72. Jogging or Hiking?
Find out how people prefer to get their heart pumping.
73. Sneakers or Sandals?
The preference says a lot about a person and how casual they are.
74. Hamburger or Taco?
Once you know, you know where to go for your next meal together.
75. Receive: Email or Letter?
Efficiency or old-school charm, what does the person prioritize?
76. Passenger or Driver?
It’s a way of finding out if the person is passive or more dominate in life.
77. Meat or Vegetables?
The answer probably shows how health conscious they are.
78. TV or Book?
How do they get their relaxing entertainment?
79. Movie at Home or Movie at the Theater?
Do they prefer to be relaxed at home or laughing with a group?
80. Horror Movie or Comedy Movie?
Are they looking for thrills or a good laugh when they want to unwind?
81. Name brand or discount?
There’s a certain kind of cool to each choice, but which one do they prefer?
82. Rich or successful?
Throw people off by making them choose.
83. Rap or rock?
Settle their musical preferences with one question.
84. Flying or driving?
Is it the quick route or the scenic route they prefer?
85. Bicycle or motorcycle?
A great test to see if they are exercise-conscious or rebellious.
86. Dancing or singing?
How do they get down to their favorite tunes?
Perhaps all the best deep questions to ask really come down to a this or that choice. Light or dark, yes or no, to be or not to be.
Drop these in a conversation with people who have a lot to say about the serious side of life, and take the conversation in a new thoughtful, deep direction.
Here are 15 great deep this or that questions:
87. Rich Friend or Loyal Friend?
A way to find out what friendship actually means to people.
88. Work Hard or Play Hard?
Get into what we’re really here to do anyway.
89. Most important in a partner: Intelligent or Funny?
What quality really makes a person worth being with?
90. Money or Free Time?
What are we actually working for?
91. Save or Spend?
Live now or prepare for later?
92. Honesty or Other’s Feelings?
Which is more important to consider in tough situations?
93. Introvert or extrovert?
Is one or the other a better way to deal with the world?
94. Marry or live-in relationship?
Discuss the best way to create a relationship that lasts.
95. Sunrise or sunset?
A chance to open up about the best moments that happen at dusk.
96. School or no school?
Do you learn more in school or just being amongst people?
97. Life or death?
This could go anywhere, but it’ll be deep no matter the direction.
98. Sinful or righteous?
Is it better to be admired as a saint or enjoy all the sinful delights of the devils?
99. Badly wounded or dead?
Is it better to suffer or to end life when it isn’t possible to live how you want?
100. Forgotten or remembered for all the wrong reasons?
How important is it to be remembered? Is it worth being remembered wrongly?
101. Rich and bored or employed and tired?
Choose the life you’d rather have, and discuss how that life could have meaning.
How to Ask This or That Questions: 3 Steps to Ask
This or that questions are perhaps one of the easiest types to ask, and so you really only need to work through a few quick steps. Here are 3 steps to ask a this or that question:
1. Choose the right moment
Here, you need to make sure people are in a conversational mood. Don’t start dropping funny this or that questions right before a serious board meeting.
Use them when people are relaxed and want to have a good chat.
2. Tailor your questions to the situation
If the person is serious, use a deep this or that question. If they’re more laid back, go with a funny one.
Pick questions that, to the best of your knowledge, will amuse and intrigue your conversation partner.
3. Spring them as a surprise
This is the real trick behind a this or that question: they’re best when they’re unexpected. Fire one off to get an instant, first impression response.
That’ll tell you more about the person and lead to better conversations.
Downloadable List of This or That Questions
Here is a downloadable list of this or that questions (right click the image and select Save Image As…):
More Great Questions to Ask
The questions don’t end with “this or that.” We have plenty more for you, so be sure to check out these articles:
- If you want more choice-based questions, look at our Would You Rather Questions.
- Just want something to keep the fun going? Click on our Fun Questions to Ask.
- Or, just keep them guessing what’s coming next with these Random Questions to Ask.
There are many ways to give a lagging conversation a boost, but perhaps the easiest ever invented is the this or that question.
Of all the clever comments or interesting questions to ask, this or that questions take the least amount of effort and require the least amount of know how to pull off.
Just throw a quick question out there and let people work through the answers. It’s that simple. If you’ve chosen the right question, you’ll have people off and running on a new conversation, on a new topic.
There’s nothing more to it. Just use the questions above and watch your conversations begin to really take off.