99 Questions to Get To Know Someone

Tuesday, October 20, 2015

You might have 99 problems, but being out of conversational topics ain't one.
Whether these questions are being used to get over first date jitters or to keep you busy on a long roadtrip, I hope you find them both useful and fun.


A lot of people consider these to be juvenile questions, but I believe they have a purpose. If you both favorite Adam Sandler movies, you probably have compatible senses of humor. If you both love the same restaurant, then it’ll make the “where do you want to eat” question a bit simpler (unless you are me and have about three favorites for each question… whoops).

1.       What is your favorite color?
2.       What is your favorite animal?
3.       What are your favorite bands/artists?
4.       What is your favorite genre of music?
5.       What is your favorite song?
6.       What is your favorite movie?
7.       Who is your favorite actor/actress?
8.       What are your favorite things to drink?
9.       What are your favorite foods?
10.   What is your favorite meal?
11.   What are your favorite desserts?
12.   What is your favorite ice-cream flavor?
13.   What is your favorite restaurant?
14.   What is your favorite fruit?
15.   What is your favorite cereal?
16.   What is your favorite pop?
17.   What is your favorite Slurpee flavor?
18.   What is your favorite drink on a cold winter night?
19.   What is your favorite drink on a hot summer day?
20.   What are your favorite books?
21.   What is your favorite holiday?
22.   What is your favorite season?
23.   What is your favorite type of weather?
24.   What is your favorite board game?
25.   What is your favorite video game?
26.   What was your favorite childhood toy?
27.   What is your favorite website?
28.   What is your favorite sport?
29.   What is your favorite day of the week?
30.   What is your favorite number?
31.   What is your favorite place (city, state, country, room, etc.)
32.   What is your favorite type of car/truck?
33.   What is your favorite quote?
34.   What is your favorite flower?
35.   What were your favorite TV shows as a child?


Either/or questions can be a lot of fun! There is no third option, so it forces the answerer to choose. Also, these questions show quite a similarity to the “would you rather” ones which are always a blast! 

36.    Coke or Pepsi?
37.    Cats or dogs?
38.    Pick-up truck or car?
39.   City or country?
40.   Backpack through Europe or lay out on a beach?
41.   Go out or stay in?
42.   Sky dive or bungee jump?
43.  Oreos or Chips Ahoy?
44.   Coffee or tea?
45.   Chocolate or vanilla?
46.   Call or text?
47.   Comedy or horror?
48.   Pen or pencil?
49.   Early bird or night owl?
50.   Pancakes or waffles?
51.   Dress down or dress up?
52.   Sausage or bacon?
53.   Math or English?
54. Pizza or tacos?
55. Beach or mountains?


Yes, these are things you probably know about someone relatively fast. But if you don’t yet know them, then why not just come out and ask?

56.  Do you have any siblings?
57.  Do you have any pets?
58.  Where are you from?
59.  What is your full name?
60.  When is your birthday?

Random, but still interesting…

61.       Do you sing in the shower?
62.       If you had to make an iPod playlist named after me, what songs would be on it?
63.       If you could have any super power for a day, what would it be?
64.       What is your best joke?
65.       What is your favorite pickup line?


No, not all of these questions involve someone to reveal their deepest darkest secrets, but they can give you an insight to what kind of person they are or what they want in life.

66.   What always makes you smile?
67.   Are you religious?
68.   What are your pet peeves?
69.   Who knows you best?
71.   What is your favorite thing about yourself?
72.   What are your worst habits?
73.   What are your biggest fears?
74.   What is the nicest thing someone could say about you?
75.   What do you wish more of your friends would do with you?
76.   What is your dream job? What is stopping you from making it your reality?
77.   What is your most embarrassing memory?
78.   How are you contributing to the world?
79.   If you could have lunch with five people, dead or alive, who would they be?
80.   Do you have any tattoos/piercings?
81.   Have you ever cheated or been cheated on?
82.   Have you ever been in a fist fight? If so, why?
83.   How old were you when you had your first crush?
84.   Do you have an interesting/funny first kiss story?
85.   If you could travel anywhere in the world, where would you go?
86.   What is the craziest thing you’ve done?
87.   What motivates you in life?
89. If money was no an object, how would you spend the day?
90. What is your biggest regret?

If you like like them:

These questions verge on flirtacious, but still come off friendly enough where you aren’t blurting out “do you like me”. Finding out what they want and what they don’t want can be a great insight to whether or not you’ll be compatible for a long term relationship.

91.       What are the top 5 qualities you look for in someone?
92.       What are your biggest turn-ons?
93.       What are your biggest turn-offs?
94.       What are your biggest dealbreakers?
95.       What is your idea of a perfect date?
96.       What was your first impression of me?
97.       What do you like about me?
98.       What don’t you like about me?
99.       What are you looking for (hookup, relationship, friendship, etc.)?

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