The best way to get to know a guy better is to ask him questions.
You will learn more about his mood and his personality by asking him basic questions or what he thinks about different topics. It is also a great conversation starter when you have run out of things to say.
Having the right questions to ask a guy will put your relationship, either platonic or romantic, on a new level. It can make you realize how much you mean to each other. It shows you’re interested and that you care to ask questions.
These are good questions to ask a guy if you want to learn more about him, become his friend, get closer, and if you want the guy, you like to feel special around you.
Questions to ask a Guy about Life
1.) Do you consider yourself a religious or spiritual person?
2.) If you could stay one age forever, what age would you choose?
3.) What part of your childhood are you most nostalgic for?
4.) Where do you see yourself in five years? How about ten?
5.) If you could re-do one day in your life, what would it be and why?
6.) How important is money to you?
7.) What big event do you think will happen soon that most people aren’t expecting?
8.) Who is the most creative person you know?
9.) What small change significantly improves a person’s appearance?
10.) What things won’t you compromise on?
11.) Who did you use to look up to, but they screwed up, and you lost faith in them?
Essential Questions to ask a Guy
12.) What scares you the most about getting older?
13.) Have you ever experienced heartbreak?
14.) Where do you escape when you want peace?
15.) What are your views on women?
16.) Do you believe in fate or free will?
17.) Is there anything I’ve ever done to offend you?
18.) What was the biggest realization you had about yourself?
19.) What’s your best example of easy come, easy go?
20.) How do you deal with difficult situations?
21.) What are the times you are most inspired, most motivated, and most charged up?
22.) What’s your next goal, big or small, you want to accomplish?
Romantic Questions to ask a Guy
23.) Do you believe in love at first sight?
24.) Do you think you’ve ever been in love?
25.) What makes you fall in love with someone?
26.) Who was your first kiss?
27.) What topic could you spend hours talking about?
28.) What do you value most about our relationship?
Flirty Questions for a Guy
29.) If you fall for someone, do you wait to say so until it feels socially appropriate, or do you spill your guts?
30.) What would you do if you had off from work today?
31.) What is your idea of a perfect Sunday afternoon?
32.) Are you a show-off when you like a girl, or do you play it cool?
33.) Does the idea of a spontaneous date interest you?
Fun Questions to ask a Guy
34.) If you could have one superpower, which would it be?
35.) If you could only eat pizza, wings, or burgers for the rest of your life, which would you choose?
36.) If you had to change your name, what would your new one be?
37.) What slang word do you wish would come back?
38.) Tell me about the best vacation you’ve ever taken.
39.) What three things would you bring with you to a deserted island?
40.) What would be an accurate tagline for each month?
41.) If you could talk to animals and they would understand you, but you couldn’t understand them, what would you do with that power?
42.) If you were a clown-themed superhero, what powers would you have?
43.) What’s the best way you or someone you know has gotten out of a ticket/trouble with the law?
44.) If you could trade places for someone for the day, who would you choose and why?
Hard Questions to Inquire of a Man
45.) What song could you listen to on repeat for the rest of your life?
46.) If you have siblings, do you feel closer to one than others?
47.) Which apocalyptic dystopia do you think is most likely?
48.) Tear gas makes people cry, and laughing gas makes people giggle; what other kinds of gases do you wish existed?
49.) What do many people have extreme opinions about, even though they know very little about it?
50.) What’s something kids today wish you had growing up?
51.) What cliche saying do you hate hearing the most?
52.) Are you receptive to new ideas and viewpoints?
53.) How would your parents describe you as a child?
54.) What’s the most boring sport, and what would you do to make it more exciting?
55.) If a movie was being made about your life, what actor would play you? What actress would play your love interest?
Random Questions to ask a Guy
56.) Have you ever participated in a protest?
57.) Do you believe in ghosts or any paranormal activity?
58.) Do you ever feel like you had a past life?
59.) Which celebrities have you met?
60.) Would you rather be a famous musician or famous actor?
61.) What is your weirdest scar, and how did you get it?
62.) Which emojis do you use the most?
63.) If you and I were to go to jail, what would it be for?
64.) At an amusement park, what ride do you have to go on?
65.) What’s the funniest joke you’ve ever heard?
66.) What instrument would you like to learn how to play?
67.) If you had 24 hours to do whatever you wanted in this city, what would you do?
Deep Questions to ask a Guy
68.) What advice would you give to your younger self?
69.) If you could live in any period of history, when would it be and why?
70.) Do you have any regrets?
71.) Should men and women have different roles in a relationship, or should it be based on individual strengths and weaknesses?
72.) What is the most significant risk you’ve ever taken?
73.) What is the most significant risk you’ve ever taken?
74.) If you were a girl for a day, what would be the first thing you do?
75.) Is there anything you’d like to change about your life?
76.) What do you want to be remembered for after you die?
77.) What does emotional maturity mean to you?
78.) What cause have you volunteered for that you feel passionate about?
79.) Is there anything about our relationship that makes you feel lonely or unloved?
Good Questions to ask a Man
80.) Have you ever felt betrayed by someone?
81.) What thoughts keep you awake at night?
82.) Do you consider yourself to be an intelligent person?
83.) What’s your best story of you or someone else trying to be sneaky and failing miserably?
84.) What sport could you play the longest in a televised game without anyone discovering you aren’t a professional athlete?
85.) Why didn’t your last relationship work out?
86.) What do you look for in a girl?
87.) Which fiction author would you love to sit down and chat with?
88.) Have you ever slept with stuffed animals?
89.) What’s your favorite physical attribute about yourself?
90.) What makes you attracted to people?
91.) What’s the best compliment you’ve ever received?
92.) What can I do to help you more?
93.) What always cheers you up when you think about it?
94.) What are you looking forward to right now?
95.) What movie do you like us to watch together?
96.) Have you ever kissed someone under mistletoe?
97.) What do I do that makes you feel loved and appreciated?
Interesting Questions to ask a Guy
98.) What’s the first thing you do when you wake up in the morning?
99.) What’s the craziest thing on your bucket list?
100.) What secret obsession do you have that I don’t know?
101.) What’s the most incredible animal you’ve seen in the wild?
102.) Do you know your love language?
103.) What word do you always misspell?
104.) Do you lie to yourself?
105.) What naps are the most satisfying?
106.) What’s your favorite holiday movie?
107.) If cartoon physics suddenly replaced real physics, what are some things you would want to try?
108.) What are your favorite pet names for girlfriends?
109.) What story you’ve heard has stayed with you and always disturbs you whenever you think about it?
110.) How many books do you read per month?
111.) What does your dream future look like?
Questions to ask a Guy to Get to Know Him Better
112.) What’s your favorite dessert?
113.) Who is your favorite musician or band?
114.) Do you consider yourself an early bird or a night owl?
115.) Out of all your family members, who are you the closest with?
116.) Which would be harder for you to give up: coffee or alcohol?
117.) Are you passionate about politics or prefer to avoid political discussions?
118.) Did you have a nickname when you were growing up? If so, what was it, and where did it come from?
119.) Have you ever bullied someone, or has someone bullied you before?
120.) What’s your secret talent?
121.) Do you believe in karma?
122.) Do you prefer to stay in or go out on the weekend?
Questions to ask a Guy Over Text
123.) What are your pronouns?
124.) When was the last time you told someone you loved them?
125.) What’s your biggest pet peeve?
126.) Have you ever screenshot a sweet text that someone sent to you?
127.) What are you looking for in a friendship?
128.) If you were elected President, what would be your first act?
129.) What is something you’ve learned from our friendship?
130.) What do you like about where you work?
131.) What qualities do all your friends have in common?
132.) If you could turn your hobby into a job, would you? Or would you keep it as your hobby?
133.) Do you find it unattractive if the girl you’re seeing makes a drastic physical change, such as hair color or cut?
134.) Have you ever snooped on a partner?
Questions to ask your Boyfriend
135.) Do you remember how we first met?
136.) What’s the proudest you’ve ever been of me?
137.) When was the last time you were jealous, and why?
138.) What do you lie most about?
139.) Did you and your friends like to hang out anywhere special as a teenager?
140.) How do you think you’ve changed over the last few years?
141.) Would you wait for me to watch the next episode of a TV show we started together?
142.) Have you ever cheated on anyone? Have you ever been cheated on?
143.) Who is the strongest woman that you know?
144.) Do you see our differences as positive or negative?
145.) What’s one thing I do that you wish I would stop doing?
146.) How have you felt fulfilled in our relationship?
147.) If you could only use three words to describe me, what would they be?
Questions to ask a Guy you Like
148.) What’s your favorite meal of the day: breakfast, lunch, or dinner?
149.) What’s your most embarrassing moment?
150.) Have you ever experienced a friendship breakup?
151.) What qualities do you look for in a partner?
152.) What’s your favorite viral video?
153.) What are your religious and political views?
154.) What is your ideal life partner like?
155.) If you could go to dinner with anyone in the world, who would it NOT be and why?
156.) Which song lyric speaks to you the most?
157.) What makes you fall in love with someone?
158.) What restaurant would you choose if you could only eat at one restaurant for the rest of your life?
159.) Who are you taking if you could take only one person on an all-expenses-paid vacation?
Questions to ask a Guy Before Dating
160.) What was the best date you’ve ever been on? The worst?
161.) Was there any instance that your parents or family did not like your significant other?
162.) What do you consider red flags in relationships?
163.) What do you take the most pictures of?
164.) What was your first impression of me?
165.) What do you consider cheating?
166.) Do you like things to be carefully planned, or do you prefer to go with the flow?
167.) Have you ever been in love?
168.) How many times have you been in love?
169.) Do you want kids?
170.) If you could only describe yourself in three words, what would they be?
171.) Do you see yourself getting married someday?
172.) What do you want out of this relationship?
Would You Rather Questions to ask a Guy
173.) Would you rather live by the beach or up in the mountains?
174.) Would you rather be stuck in traffic for three hours or never get to a fast food chain again?
175.) Would you rather live in one place for a very long time or live in many areas and move around?
176.) Would you rather time travel to the past or the future?
177.) Would you rather be able to ctrl + f to find anything or ctrl + x to cut anything out of your life?
178.) Would you rather get money every time you coughed or be able to stretch your limbs up to six meters?
179.) Would you rather be rich but stupid or a poor genius?
180.) Would you rather be colorblind or unable to smell?
181.) Would you rather always be on the edge of a sneeze that won’t come or an itch you can’t scratch?
182.) Would you rather only speak English or speak every language other than English?
183.) Would you rather sleep in a hammock or a tent for the rest of your life?
This or That Questions to ask a Guy
184.) Amusement Park or Day at the Beach?
185.) Television series or movies?
186.) At a movie: Candy or popcorn?
187.) Delivery or sit-down restaurant?
188.) Chocolate or vanilla?
189.) Night or morning?
190.) Football or basketball?
191.) Console Gaming or PC Gaming?
192.) Car or Truck?
193.) Blue or Red?
194.) Rock or hip hop?
195.) Money or Free Time?
196.) Spend your money or save your money?
197.) Batting or pitching?
198.) Apple or PC?
199.) Ketchup or Salsa?
200.) Tennis or pickleball?
201.) Pepsi or Coke?
202.) Pretzels or Potato Chips?
Questions to Ask a Guy FAQs
Here are some frequently asked questions on the topic: questions to ask a guy.
“Does the idea of a spontaneous date interest you?” and “What do you look for in a girl that you want to date?” come to mind.
1.) Which song lyrics speak to you the most? 2.) What makes you fall in love with someone? 3.) What was your first impression of me?
1.) Who is the strongest woman that you know? 2.) If you could only use three words to describe me, what would they be? 3.) What’s your favorite way to spend a Sunday afternoon?
Final Thoughts on Asking Men Questions
Since getting to know someone takes time and effort, balancing the need for an exciting and inventive line of questioning with easy and familiar conversations is essential.
Some people aren’t great at small talk, so the best way to avoid it might be a list of questions designed to help you get to know a guy better.
Always remember that the goal is to get closer to open communication, so asking questions in such a list should focus more on getting answers rather than keeping the conversation going. And don’t forget to listen just as much as you talk!
By Emily Vaughn
Emily writes about relationships, romance, and dating.
You are on the Questions To Ask a Guy page.
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