Have you ever been in the following awkward situation? You haven’t seen a friend in a long time, you’re catching up over a cup of coffee, and you have dead air while your mind is blank.
A few things build those uncomfortable silences, and we must know how we can avoid them in the future.
Here are plenty of questions to ask a friend and keep the conversation flowing.
Questions to ask your best friend
1.) Do you think we’ll always be friends?
2.) What age would you like to get married?
3.) Do you know my middle name?
4.) Are you more into brains or looks?
5.) Do you know when my birthday is?
6.) When can we hang out again?
7.) What do you think the best way to resolve conflict is?
8.) Would you trust me with something you wouldn’t trust with anyone else?
9.) What excuse do you commonly use to get out of plans?
10.) What is the best pickup line you’ve ever used? Heard?
11.) Where have you been wanting to travel but haven’t had the chance to visit?
12.) Have I ever said or done anything that offended you without realizing it?
13.) Who do you hate, and why do you hate them?
14.) If I could help you do one thing this weekend, what would it be?
15.) What’s the last thing you bought online that you loved?
Personal questions to ask a friend
16.) Have you ever bullied someone?
17.) What’s on your bucket list?
18.) How would you rank the following in importance: family, career, and love life?
19.) Do you think you’re brave?
20.) What book has impacted you the most?
21.) What personal passion project are you working on right now?
22.) How did you handle your childhood pet passing away if you had any?
23.) What’s the best advice a family member gave you growing up?
24.) On a scale of one to ten, how would you rate your current job?
25.) Do you see yourself working in your present job even after ten years?
26.) Do you like to recharge alone or around other people?
27.) Are you still in touch with your childhood friends?
28.) Do you want kids? If so, would you prefer to have a baby without a partner or a partner without a baby?
29.) How do you plan to spend your retirement?
Thoughtful questions to ask a friend
30.) Does anything keep you up at night?
31.) Do you like surprises?
32.) Is there something you need help with at this moment?
33.) When you feel self-doubt, how do you push through it?
34.) With all honesty, how are you feeling?
35.) What emotion do you experience the most?
36.) What does “getting out of your comfort zone” look like for you?
37.) What would help you feel the most relaxed right now?
38.) What are you grateful for today?
39.) What was your favorite Halloween costume you ever wore?
40.) When you’re in a bad mood, is there something or someone that can instantly make it better? Who or what?
41.) Is it easy or difficult for you to accept help from people?
42.) Are there certain things we’ve never done together that you want to do?
Quizzing your pals
43.) What’s the weirdest app you have on your phone?
44.) If you were a cereal, which one would you be and why?
45.) What is your most-used emoji?
46.) What’s your funniest first-date story?
47.) Who was the last person you stalked on social media?
48.) Do you check your Instagram stories to see if someone specifically watched them? Who?
49.) Who is your celebrity doppelganger?
50.) Which meme have you seen that made you laugh the hardest?
51.) If you could steal one thing from my closet for yourself, what would it be?
52.) If you find yourself stranded on a deserted island, what three things would you want to have with you?
53.) If you had to listen to one song for the rest of your life, what would it be?
54.) Which celeb would you want as your other best friend and why?
55.) What has been your most questionable haircut or fashion moment?
Hard questions to ask a friend
56.) If you were to have children, how would you raise them?
57.) If you had to choose between cute clothes or never wearing makeup, which would you choose?
58.) How long can you go without checking your phone?
59.) Why do you think popular kids are popular?
60.) Who was your first friend, and are they still in your life?
61.) When was the last time you cried, and why?
62.) How do you contribute to a better society?
63.) Imagine you could eliminate plastic or air pollution; which would you pick?
64.) How can you describe what you do in life to a 6-year-old kid?
65.) If you had to choose between losing a hand or a leg, which would you choose?
66.) What makes you feel the most alive?
67.) If you had to choose between not being able to hear people speak or not hearing music, which would you choose?
68.) If I called you in the middle of the night, would you pick me up?
69.) What do you value most in a friend or partner?
70.) Would you rather have an infinite number of good friends or two incredible, loyal, absolute best friends?
71.) What would you do if you could do anything knowing you would not fail?
Random inquiries for your buddy
72.) Where would you go if you could travel anywhere without worrying about the cost?
73.) What was the last picture you took?
74.) How do you think you will die?
75.) Is your career path the same as your college degree?
76.) Which account do you follow on social media?
77.) How many times can you watch the same movie?
78.) What is the best part about taking a selfie?
79.) What’s the best compliment you’ve ever received?
80.) Why is it called lipstick if it doesn’t stick your lips together?
81.) If you were to remove one social media app from your phone, which would it be and why?
82.) Imagine you could be good at sports or business; what would you choose?
83.) What country would you own if you could own one?
84.) How can a new word be invented and put into the dictionary?
85.) If you could change your first name, what would you change it to?
Questions to ask a friend about love and relationships
86.) What qualities attract you most in a love interest?
87.) What do you think makes a relationship more robust and last longer?
88.) What things do you consider to be deal breakers when in a relationship?
89.) What qualities are you looking for in someone you want to spend your life with?
90.) Would you ever consider being in a long-distance relationship?
91.) Do you think it’s essential that the person you are dating is intelligent?
92.) What lessons did your previous romantic relationship teach you, and why did it end?
93.) Do you prefer dating just one person and see where it goes or dating multiple people until you decide?
94.) If you could marry anyone in the world, who would it be and why?
95.) What do you look for when seeking a new partner or love interest?
96.) What makes you most uncomfortable about dating?
97.) Would you be with someone who doesn’t have the same personal beliefs as you?
Deep questions to ask a friend
98.) How do you feel about faith and spirituality?
99.) What’s the deepest desire of your heart?
100.) What does this friendship mean to you?
101.) What are your thoughts on marriage?
102.) What scares you most about your future?
103.) Are you more afraid of death or not living?
104.) When do you think you’ll know you’ve met “The One”?
105.) Have you ever hurt someone and deeply regretted it? Did you ever make amends?
106.) Do you believe your priorities will shift over time or remain consistent?
107.) Would you pick your current career again or do something different?
108.) Do you often worry about things you have no control over?
109.) How often do you have deep and emotional conversations with someone?
110.) What would our world look like if money didn’t exist?
111.) Do you usually follow your heart, head, or gut feeling?
Good conversation starters for those close to you
112.) What do you usually do to reduce stress?
113.) What’s the first thing you do every morning?
114.) If you could immediately have your dream body, but it would give your best friend thirty extra pounds, would you do it?
115.) Do you consider yourself organized?
116.) Do you believe in miracles?
117.) What is the most memorable experience that you’ve done with someone?
118.) What is your key to a cozy evening?
119.) What business would you start if you had an unlimited amount of money?
120.) What’s the one snack you can’t live without?
121.) Where do you want to travel the most?
Conversation starters with friends
122.) Do you want kids of your own?
123.) Did you ever get fired from a job?
124.) Have you ever kept a journal?
125.) What’s a fun fact you know?
126.) Do you have any tattoos?
127.) What TV show are you in the middle of watching?
128.) Do you listen to podcasts?
129.) Do you enjoy discussing politics?
130.) What music do you listen to when you need background noise?
131.) What was the last thing you watched?
132.) What do you do while you are in line for an appointment?
133.) Which meal is your favorite: breakfast, lunch, or dinner?
Interesting questions to ask a friend
134.) What was your first car?
135.) What’s the nicest compliment you’ve ever received? From who?
136.) Since you’ve turned 21, what’s the most extended amount of time you have gone without drinking?
137.) Do you have a favorite book you love to recommend?
138.) What’s the last video game you played?
139.) Do you speak more than one language?
140.) Where do you see yourself living when you retire?
141.) What’s your absolute favorite way to spend a weekend?
142.) What’s the earliest thing you remember as a child?
143.) How do you drink your coffee?
144.) Have you ever tripped or fallen in front of a vast crowd?
145.) If you could only communicate with one other person for the rest of your life – other than your significant other – who would you choose?
146.) What was your first impression of me when we met?
Questions to ask friends to get to know them better
147.) Have you ever won an award?
148.) Do you have a sweet tooth?
149.) Do you have any pet peeves?
150.) What’s your favorite thing to do alone?
151.) What’s your favorite drink?
152.) Have you ever been on a blind date?
153.) What is one thing you hope you accomplish by the end of the year?
154.) What’s the most annoying habit a person can have?
155.) What TV show do you watch when you want to pass the time?
156.) What personality traits in other people do you find most attractive?
157.) Is there a particular food your family always makes when they get together?
158.) What is the best birthday gift you have ever received?
“Would you rather questions” to ask a friend
159.) Would you rather live on the beach or in a cabin in the woods?
160.) Would you rather have your friend or boss fall in love with you?
161.) Would you rather have your pet(s) live your entire life or have me live your entire life?
162.) Would you rather lose your passport or smartphone?
163.) Would you rather someone read your diary or someone read your text messages?
164.) Would you rather know the date of your death or the cause of your death?
165.) Would you rather prefer not having a cell phone ever again or not be able to gossip again?
166.) Would you rather be a donkey or a monkey?
167.) Would you rather be able to change one part of your body to your idea of perfection or have the best wardrobe for the rest of your life?
168.) Would you rather give up all video streaming services or give up listening to music?
169.) Would you rather get a tattoo or a lip piercing?
170.) Would you rather have front-row seats to a musician you’ve never heard of or sit in the parking lot and watch your favorite band perform?
171.) Would you rather never get angry or never be envious?
172.) Would you rather have a partner snore every night or be the partner who snores?
173.) Would you rather dumpster dive for food or ask customers outside a restaurant to buy you a meal?
174.) Would you rather have super sensitive taste buds or super sensitive hearing?
175.) Would you rather have a million dollars, or would you rather be in a healthy relationship?
176.) Would you rather have to cook the big holiday meal every year or clean up and do the dishes afterward?
“This or that questions” to ask a friend
177.) Sushi or ramen?
178.) Be a regular person or a celebrity?
179.) Rich or tall?
180.) Sleep in complete darkness or with the lights on?
181.) Fruit juice or alcoholic beverage?
182.) Polaroid or digital cameras?
183.) Call or text?
184.) Reading a book or listening to an audiobook?
185.) Do the laundry or do the dishes?
186.) Eat instant noodles for breakfast or eat cereal for dinner?
187.) Saving or spending?
188.) Keep a secret or tell a secret?
See more “This or That Questions.”
189.) Have children or adopt children?
190.) Be the oldest sibling out of seven brothers or be the youngest?
191.) Bungee jumping or skydiving?
192.) Start a business or work at a job?
193.) Soda or milkshakes?
194.) Hiking or fishing?
195.) Live in 1960 or 2060?
196.) Ketchup or salsa?
198.) Sunrises or Sunsets?
199.) Spring or Fall?
200.) Podcasts or Audible books?
Final thoughts on questions for friends
After reading this, you should know more about what to ask friends. It’s not as challenging to think of questions to ask your friends as you might imagine, especially if you’re getting together for some quality time.
Sometimes the best questions to ask your friends are the ones that challenge them or allow them to open up and share some things with you that they wouldn’t share otherwise. Good luck with your next catch-up!
Athena writes about pop culture, literature, and history.
You are on our Questions To Ask a Friend page.
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