160 Questions To Ask A Guy To Get To Know Him Better

Starting out a new relationship? Or just want to get to know your boyfriend better? Communication is the key to understanding a person who matters to you. Which is why, I decided to make a list of questions that will help you get to know a guy better. We often hesitate in asking questions, whether it is the first date or months down the line. You tend to think it might make your partner uncomfortable. However, I made a list of 160 questions to ask a boy to get to know him better without being rude, harsh or blunt.

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From sexy to funny, and some intimate thing with a guy, this wide range of questions will help get the awkwardness out of the way and bridge your communication gap. 20 questions for every situation, no matter where your relationship is heading!

20 Questions When You’ve Just Started Dating

When you’ve just begun seeing someone, it is obvious that you do not know everything about them yet. And initiating conversations can get a little tricky. Though some conversations flow endlessly, there are some important questions that will open up a delightful treasure of stories you’ll both love to share. Here are 20 questions that will help you get to know your new love interest better.

1. What is your most memorable childhood birthday?
2. What’s a random hobby you’ve always wanted to try but never have?
3. What’s your guilty pleasure snack, drink, or junk food?
4. How do you like to spend your weekends?
5. What puts you in a good mood instantly?
6. What’s your favorite social media profile?
7. Which song makes your bad day better?
8. What pets have you had?
9. Are you a morning person or a night owl?
10. How many siblings do you have?
11. Tell me something about your family.
12. What’s the best thing that has happened to you this month?
13. What’s your ideal first date like?
14. What’s your favorite app on your phone?
15. What’s the silliest fear you have? That you can’t seem to get rid of.
16. What would you consider your one true talent?
17. Which country have you always wanted to visit?
18. What helps you relax?
19. Who’s your favorite character from a TV show, movie, or book?
20. What’s the most recent thing you’ve done for the first time?

20 Intimate Questions To Ask A Guy

Replace your next movie night with a fun question and answer round where you and your partner can get to know each other better. These 20 intimate questions will not just bring the both of you closer but also help you understand the other person better. From recalling the first date, to being honest with each other about what you dislike. Get ready to open the floodgates with this set.

1. What’s the first thing you noticed about me?
2. What did you think of our first date?
3. When did you decide that you wanted to date me?
4. Have you ever been in love?
5. Have you ever cheated in a relationship?
6. What’s your relationship history?
7. How would you define love?
8. What’s that one thing you can never forgive yourself about?
9. Have you ever intentionally hurt someone?
10. Have you ever felt hurt by something I did or said?
11. What do you like the most about me?
12. What do you dislike the most about me?
13. Are you completely yourself when you are with me?
14. Which side of you do you often hide? What holds you back in a relationship?
15. Who is the kindest person you know?
16. What was the ideal time of your life? When you were the happiest.
17. What’s the most essential aspect of a good relationship?
18. What to you, is a perfect relationship?
19. How would you like to shower affection on your partner?
20. What’s that one thing that could ruin our relationship?

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20 ‘Where Are We Going?’ Questions

The much dreaded question, ‘Where are we going?’ haunts every relationship. But why, Ladies? This question isn’t meant to scare your partner away. Instead, take this as an opportunity to discuss the serious issues in your relationship. From the daunting long-term questions to the nitty gritties of each others characteristics, here are 20 questions that are a great alternative to the boring ‘Where are we going?’

1. Where do you see us in the next five years?
2. Do you see a future with me?
3. What is your greatest fear when it comes to our relationship?
4. What sets us apart from other couples?
5. What is a strict no-no in a relationship?
6. Do any of my habits make you insecure or uncomfortable?
7. If you could change one thing about our relationship, what would it be?
8. Do you believe in long-term relationships?
9. How important is our relationship to you?
10. Is long distance relationship on the cards?
11. What has been our worst date so far?
12. What has been our best date so far?
13. What is that one thing about me that embarrasses you?
14. Which friend of mine can you never imagine yourself getting along with?
15. What is the fondest memory you have of the two of us?
16. Which movie couple do you think we resemble?
17. What is the one quality you think a healthy couple should have?
18. Do you have any relationship milestones you want us to achieve?
19. How often do you think about me in a day?
20. Do you see us living together one day?

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20 Sexy Questions To Ask A Guy

Looking to get down and dirty with your boyfriend? I have some 20 dirty questions that might just be the foreplay you need. From the fantasies he never talks about to the forbidden threesome, use this opportunity to discuss your sexy time needs.

1. If you could ask me for three wishes, what would they be?
2. What kind of an outfit would you like to see me in?
3. What is your favorite part of my body?
4. What is your biggest fantasy?
5. Where do you want to have sex next?
6. What is your favourite position?
7. Do you like the lights on or off?
8. Do you think that I am a good kisser?
9. What kind of foreplay are you into?
10. Would you ever want to have sex in public?
11. What do you think is the most sexiest thing about me?
12. What kind of lingerie would you like to see me in?
13. Have you ever had a one night stand?
14. Can you unhook my bra with one hand?
15. Do you like talking dirty?
16. Name one habit of mine that immediately turns you on?
17. Which position would you like to try?
18. Do you enjoy more when I’m on top or when I’m on the bottom?
19. Have you ever considered a threesome?
20. Have you ever stripped for someone?

20 Funny Questions To Ask A Guy

Looking for a fun way to kick start your second date? Or are you and your partner just bored and waiting in a line? These funny questions will surely boost your mood and help lift your spirit, no matter where you are. From recollecting his funniest childhood memory to hearing his worst pick-up line, there are no secrets left in his closet!

1. What’s your fondest childhood memory?
2. Which sport would you like to play?
3. What’s the meanest thing you’ve ever said to someone, just to be spiteful?
4. What’s your go-to pick-up line?
5. What’s the lamest excuse you’ve made to get out of a date?
6. If you had to imitate me, which line would you use?
7. Which word do I use too much of?
8. If you had to have the ‘sex-talk’ with your kid, how would you do it?
9. What’s the funniest rejection you’ve ever faced?
10. Tell me your funniest joke.
11. What is your most (second-hand) embarrassing moment?
12. What would you change your name to, if you could?
13. What would a reality TV show made on your life be called?
14. What’s your favorite piece of technology?
15. Which scene from a movie or a TV show has happened to you in real life?
16. If you could be an inanimate object, what would you be?
17. What’s that one thing you can’t leave, even if it got illegal?
18. What’s the funniest story you have from your childhood?
19. If you ever had to get your portrait painted, which pose would you pick?
20. What would your wild DJ name be?

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20 Questions To Ask If You Want To Get Married

Thinking of tying the knot? Well, it may be a love or an arranged marriage but there are some questions you should get out of the way before proposing for marriage. From the kind of space he requires in a relationship to if he is a workaholic, it will give you a deeper insight into the life you both are going to share ahead. This is also a chance to get to know your life partner better, dig in!

1. What would you really want to do with our free time?
2. Do you feel crowded by people often?
3. Have you ever thought how many kids you’d want to have?
4. Do you think we should have long-term marriage goals?
5. Do you make financial plans?
6. What is your every day schedule like?
7. Do you tend to mostly work? Or do you manage to get time for other things?
8. Do you drink or smoke?
9. How often do you manage to take a vacation?
10. How often do you manage to socialise?
11. Do you ever wonder if our education system is good enough?
12. How do you manage sticky situations like arguments or disagreements?
13. Do you manage to maintain a balance between your job and family?
14. What are your political views?
15. What’s your secret tip when it comes to saving money?
16. Do you have any plans as to what the wedding should be like?
17. What’s your biggest fear about being married?
18. Do you have a dream house in mind for the future?
19. What is the most exciting thing about getting married?
20. Do you want any pets?

20 Career Questions To Ask A Guy

When you begin a relationship, you don’t often talk about work. Maybe because the both of you are so tired after a long day that you just want to relax. But it is important to share this aspect of your life with each other. It shows that you are and are genuinely interested in what your partner does and want to help out and offer advice wherever you can.

1. What the best part of your job?
2. Do you already have plans for the next five years?
3. Is the atmosphere at your office cool?
4. Do you have friends at work?
5. Do you have to be competitive to get ahead in your office?
6. Does your job give you satisfaction?
7. Are you planning to switch your job anytime soon?
8. How do you see yourself growing at your workplace?
9. Which position are you eyeing next?
10. Is there a dream company you would love to work at.
11. If you had a shop, what would you sell?
12. What does an ideal day at work look like?
13. Do you manage to make time for your friends post-work hours?
14. What has been the highlight of your career, so far?
15. Are you excited to go to work every morning?
16. What do you consider your greatest skill?
17. Did you incorporate any hobby into your career?
18. What made you pick this field?
19. If you weren’t working in this field, what else do you see yourself doing?
20. How do you deal with uncomfortable situations at your workplace?

Also Read: Questions to ask your crush

Images – Giphy, YRF

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This story was updated in 2019.