Dating 101: 191 Dating Questions
I went on my first date when I was 16. I met him through a mutual friend and we went to Chili’s. When I got there, his friend Phillip was there… Yeah. I didn’t know why and I didn’t ask. But I had enough sense not to continue anything with him after that.
First dates can be nerve-wracking especially if you’re not used to going on them regularly or if you’ve never been on one at all. From insecurity about your hair, makeup, and outfit to having no idea what to talk about and feeling awkward. Shoot, you might even feel annoyed that you might be wasting your time with yet another date that leads nowhere.
Though I’ve been on my fair share of dates, I am very selective (as we all should be) with who I choose to spend my time with.
My best advice is this:
BE YOU. Be your authentic and unique self and don’t ever put on a front. Who God has for you, is for you and nothing can change that.
Interview and collect data, but don’t interrogate. You are asking questions to figure out if and how you’d like to keep someone in your life. They could be a potential friend, business or ministry connection, and/or connection for someone else.
Listen to understand, not necessarily to respond.
Decide what questions are the most important to you to ask each time you go out with someone.
Don’t force a connection or attraction. It should happen naturally.
My friend Alex suggests asking your date this: “In the event that one of us is not feeling the other for whatever reason, how do we want to end things or proceed as just being friends/friendly?” This way you can avoid possible awkwardness if you’re not feeling the other person like that.
*Depending on where you met this man, what you already know about him, and if you’ve already gone through the Top Dating Questions, you may not need to ask some of these. Feel free to skip over them if that’s the case.*
If you won the lottery, what would you do with the money?
If someone gave you 1 million dollars, which charity would you give half to and what would you do with the rest?
If money were no object, what you do with your life?
How did you come to know Jesus? What’s your testimony? What's your spiritual background?
How has your relationship with Jesus shaped your life?
What are your views on abstinence?
What is your life mission and vision and how are you pursuing them?
What do you think about therapy? In what ways are you investing in yourself and your healing?
What makes you excited to wake up in the morning?
What are you (most) passionate about?
What lessons has God been teaching you recently?
Tell me about an article, blog post, or book that you read recently that intrigued you.
What could you give a 30-second presentation on with no preparation?
How would you describe the internet to a caveman?
Where would we go if you only had $20 for a date?
Share one thing that you love to do that you get to do nearly every day.
What makes you feel like a man?
What is your favorite thing to spend money on?
What would light up your day right now?
What do you like to do for fun/in your free time/when you’re not working?
What is something on your bucket list?
What is your idea of a healthy relationship?
What is something you’ve learned from a past relationship?
What are your top 3 goals in life?
If you could be anywhere, doing anything right now, where would you be and what would you be doing?
What would you like to be doing 5 years from now?
What do you want to do with your life?
What are your friends like? What is your social life like? Who are your closest friends?
How often do you see your close friends?
Who is your accountability? What does that mean/look like?
What are the top 5 qualities you look for in a friend?
What one modern convenience could you not live without?
If you had one extra hour of free time a day, how would you use it?
Name 2 things you consider yourself to be very good at.
What is your favorite local restaurant and the meal you most enjoy eating when there?
If you could host a talk show, who would be your first guest?
How long have you been single?
What are you looking for?
What are you currently reading?
Who is someone you look up to? Why?
Which of your friends and/or family do you look up to the most?
If you could do anything without money or time being an issue, what would you do with your life?
What do you like to do on the weekends? What is your idea of a perfect weekend? Describe your perfect weekend.
What’s your favorite thing to do?
Who are you closest to in your family?
What do you do when you don’t get what you want?
Besides me, what puts a smile on your face?
What do you find yourself daydreaming about?
Have you ever been married?
Do you have any kids?
What was your favorite Poptart flavor growing up?
If you could bring back any BLACK 90’s show indefinitely, what would it be?
When is the last time you cried? Why?
What are your strengths and weaknesses? How are you growing in them?
Be creative and think of your own fun icebreaker question!
Who should pay on the first date?
How do you like to receive love? What is the order of your love languages? (The love languages are: quality time, physical touch, words of affirmation, gifts)
What is your communication style and how do you normally like to get to know people? text? video? talk in person? coffee? walks? dinner? other outings?
Would you ever live with someone before you’re married?
What has your dating experience been like?
What is something you worked hard for and still did not get? How did you handle that loss/disappointment?
Bungee jumping or skydiving?
Pancakes or waffles?
Wealth or love?
Knowledge or power?
When is the last time you did something for the first time? What was it?
What’s your favorite dad joke?
What 3 words would you use to describe yourself?
If you could go to a concert of your 3 favorite artists, who would they be? (Sade, Tems, Ari?)
What makes you unique?
What are some random fun facts about you?
Do you have any talents?
What is something you want to learn or wish you were better at?
What book has had the greatest impact on your life?
What’s an obstacle you’re currently afraid of facing, but that you’re going to do anyway?
What were you like as a kid?
What 3 things are you wanting to accomplish this month?
If you could restart or go back to change something in your life, what would you do differently?
Would you rather…? Come up with some of your own questions.
What makes you happy? Sad? Angry?
If you joined the circus, what act would you most want to perform?
What's your favorite childhood memory? (spending the summers with my grandmother in Georgia)
What is the worst food you've ever eaten?
If you could live in any sitcom, which one would it be?
If you could vacation anywhere in the world for 2 weeks, where would you vacation? (The Maldives)
Who do people say you look like? (Jill Scott)
How would your closest and/or best friend(s) describe you? (bold, protective, loving, funny)
Ever been dumpster diving?
How do you like your burgers/steak?
What is your favorite ice cream flavor?
What makes you laugh?
What are your pet peeves?
What’s your favorite outdoor activity?
How long do you sit at a green light before honking at someone?
What made you ask me out?
If you could gain any one ability or quality that you admire in someone else what would you choose?
What is something you're unsure about in life that you’re ok with being unsure about?
What is something you get in your head about?
What is something you want to learn or wish you were better at?
What were you like as a kid?
If you could restart or go back to change something in your life, what would you do differently?
Would you rather?... (come up with some of your own would you rather questions.)
Do you know any good jokes?
What makes you laugh?
What’s the most important/valuable thing in your life?
What’s your most embarrassing moment?
What are the top 3 goals you have in your lifetime?
Where is the next place you want to travel to?
What are your 3 favorite smells?
Do you enjoy traveling? Do you want to travel more (or at all)? Where do you want to go next? What are your top places to travel?
What is your favorite place on earth?
Who are the special people in your life? Why?
What’s your idea of a perfect date?
What is the best dessert you’ve ever had?
What’s the best advice you’ve ever received?
If you could live anywhere in the world, where would it be?
What is something you’re proud of?
What was your favorite thing about where you grew up?
If tomorrow were your last day on earth, what would you do?
What is your favorite movie?
What do you like the most about yourself?
Ferret or guinea pig?
Who are some of your greatest influences?
What motivates you?
How do you define success?
121. What’s your favorite time of year?
122. Do you have social media? What’s your favorite social media outlet? Why?
123. What’s the craziest/most spontaneous thing you’ve ever done?
124. What’s your favorite thing about this city?
125. If you could relive one day from the past, which would it be and why?
126. If you could change one thing from the past, what would it be and why?
127. If you could have any talent in the world, what would it be?
128. If you could own a house or travel the world, which would you choose?
129. What do you like to do when you’re alone?
130. What’s your go-to karaoke song?
131. You're on a desert island. What one book, piece of clothing, and food item would you take?
132. What’s on the top of your bucket list at the moment?
132. If you were Miss America, what would be your platform?
133. If you could have any 3 people from history for a dinner party, who would they be and why? What would be the topics of conversation?
134. If you could tell yourself from ten years ago something, what would it be?
135. What’s something you’ve never done but want to do?
136. What are 3 pieces of wisdom you’d want to pass on to your children or any youth that you have the privilege of mentoring/pouring into?
137. What’s been your biggest regret and what did you learn from it?
138. Who has been the biggest influence on your life and decisions?
139. What motivates you the most?
140. What did you want to be when you grew up?
141. Would you change anything about your personality?
142. What’s your worst habit?
143. What’s the best gift you’ve ever received?
144. Where did you grow up?
145. What did you study in college and why?
146. What do you do to cheer yourself up?
147. Who knows you the best?
148. What subject would you like to learn more about?
149. What makes you laugh?
150. What’s your favorite food? Cuisine?
151. Are you a morning or night person?
152. What does it take for someone to become good friends with you?
153. What kinds of tv shows and movies do you like?
154. Are you more introverted, extroverted, or ambiverted?
155. What’s your favorite 80s/90s/00s song(s)?
156. What’s the funniest pick up line you’ve ever heard?
157. What would your talent be in the Miss America competition?
158. Clowns? Yea or nay?
159. If you had a Youtube channel and/or podcast, what would it be about?
160. f you had to give up one of your 5 senses, which would it be?
161. Which animal would you like to have a conversation with?
162. What’s your biggest regret purchase you’ve ever made?
163. What’s the weirdest food you’ve ever eaten?
164. Would you rather have a lot of money or true love?
165. What’s your favorite day of the week?
166. What superpower would you have?
167. What’s your favorite animal?
168. Cats, dogs, or llamas?
169. What do you think about women proposing to men?
170. What song(s) gets you on the dance floor?
171. What’s your least favorite food?
172. Who would you want to play in a movie about your life?
173. What do you have a tendency to hoard?
174. What is your favorite kid’s show that you would still watch today?
175. Have you ever been on a successful blind date?
176. Where are you most ticklish?
177. What are you really bad at?
178. What do you want to get out of your next relationship?
179. What is your quirkiest habit?
180. What is something that not many people know about you?
181. Have you ever had a run-in with the law?
182. What’s the stupidest thing you’ve ever done?
183. What are you most afraid of in life?
184. What’s something you have done that you would never tell your parents about?
185. What’s the craziest dare you’ve ever done?
186. What’s the worst lie you’ve ever told?
187. What’s one of your favorite movies and which character in the movie is most like you?
188. What is your favorite day of the year?
189. What aspect of your daily routine do you look forward to the most?
190. If my answer was yes, what would your question be to me?
191. What was your favorite class in high school and why?
