600 Questions To Ask Your Boyfriend That Will Bring You Closer

Relationships tend to get boring when both partners stop working, believing love is enough to steady their ship. While love can indeed strengthen the fabrics of your relationship, if it is not constantly fueled, it can lead to a gradual disconnect and eventual fallout.

To forestall the chances of this ever occurring in your affair, you need to take active steps to bolster the love and unity you share with your partner. One of such steps is through romantic, inquisitive, and deep questions.

There are numerous questions to ask your boyfriend to get him to open up to you about aspects of his life, his family, and your relationship together which you hitherto had no knowledge of. Remember that men are often complicated.

As such, these questions to ask your boyfriend must be carefully constructed to avoid giving a wrong impression of interrogation or fault-finding.

The reason we recommend these questions to ask your boyfriend is because when handled right, they can boost the intimacy and fervor in your relationship to levels you have never experienced.

These questions to ask your boyfriend revolve around romantic, cute, deep, and juicy issues that would capture his imagination and get him thinking seriously about the relationship.

If you are in a long-distance relationship, it is encouraged that you take these questions with utmost importance as they provide a great opportunity to spice up your relationship and fix yourself permanently in the heart of your man.

So, without further ado, let’s get into the list of fascinating questions to ask your boyfriend. Ready for the ride? Let’s go!


Romantic Questions To Ask Your Boyfriend When You Are Bored


This list of romantic questions to ask your boyfriend are the best you would find anywhere. When you have been in a relationship for a while and have talked about pretty much everything, you might find yourself getting bored.

These questions can help you connect with your partner; you will get to know them on a deeper romantic level.

1.  What does your dream wedding look like?

2.  What is your idea of a romantic honeymoon destination?

3.  How many kids do you want to have?

4.  What do you want to do on Valentine’s day?

5.  What did you think when you first saw me?

6.  Do you believe in soulmates?

7.  Would you do a time capsule for our grandkids?

8.  What is your idea of the perfect date?

9.  How would you define love?

10.  What is a relationship deal-breaker for you?

11.  What does your ideal retirement look like?

12.  What is your favorite thing about our relationship?

13.  What made you fall for me?

14.  Which of my nicknames for you is your favorite?

15.  How did our first kiss make you feel?

16.  Is there such a thing as being too much in love?

17.  What is your idea of the perfect romantic gift?

18.  What’s the most romantic movie you’ve ever seen?

19.  What is one thing I do that you will never get tired of?

20.  What is your favorite memory of us?

21.  What turns you on the most?

22.  Do I make you happy?

23.  How can I be a better woman for you?

24.  Are anniversaries important to you?

25.  What is your biggest fear in this relationship?

26.  What would be the perfect gift for you?

27.  If the world was going to end tomorrow, how would you make our last day together memorable?

28.  If you found out that I am pregnant right now, how would you react?

29.  If you could choose one romantic movie for us to star in, which would it be?

30.  Would you kiss me if people were around?

31.  If I had to move halfway across the world, would you come with me?

32.  If the house was on fire, what three things would you save?

31.  If I could only make you one meal for the rest of your life, what would it be?

32.  If we won the lottery, what would we do with the money?

33.  Would you still love me if I looked different?

34.  If you could correct one of my flaws, what would you fix?

35.  What three words would you use to describe me or our relationship?

36.  Guess what I like about you the most?

37.  How much do you think I love you?

38.  Do you prefer a passionate kiss or a long warm hug?

39.  What’s the most sensual dream you’ve ever had?

40.  Do you like hearing how beautiful you are?


41.  Guess what I like about you most.

42.  How do you like a girl to show her feelings?

43.  Describe making love in three adjectives.

44.  What’s your favorite thing about making love?

45.  What do you remember most about the night/day we first met?

46.  What about our relationship makes you really happy?

47.  How long did you think our relationship would last when we first started dating?

48.  If you had one word to describe our love what would it be?

49.  Do you believe there’s one person you’re meant to be with?

50.  Do you believe in fate? destiny?

51.  What’s one difference between us that you absolutely love?

52.  What is the hottest thing a partner can wear?

53.  Do you believe in love at first sight?

54.  What is your favorite love song?

55.  What’s one similarity between us that you absolutely love?

56.  What about me made you fall in love?

57.  Is love something that scares you?

58.  What about love scares you?

59.  What’s your favorite memory of us?

60.  What sound do you love?

61.  What are your favorite scents?

62.  What is your favorite karaoke song?

63.  What is your favorite thing to do on a rainy day?

64.  What’s one thing you want to do together that we’ve never done before?

65.  If something happened where I had to move very far away, would you attempt long-distance? Or go our separate ways?

66.  Where is your favorite place to be with me?

67.  What’s one thing you’re scared to ask me, but really want to know the answer to?

68.  What’s one thing you feel our relationship is lacking?

69.  What’s your favorite non-physical quality about me?

70.  What’s your favorite physical quality about me?

71.  If our relationship ended, what’s the one thing about it you’d miss the most?

72.  Do you think you’ve been vulnerable in our relationship?

73.  What do you think was your most vulnerable moment in our relationship?

74.  What do you think has been the hands-down funniest moment since we started dating?

75.  What’s one quality about me that I see as a flaw that you absolutely love?

76.  What’s one secret you’ve wanted to tell me, but haven’t?

77.  Do you think there’s such thing as the ‘right’ person for you?

78.  Do you think I’m the ‘right’ person for you? (If yes) What about me makes me the ‘right’ person?

79.  What fictional character do you have a crush on?

80.  Have you ever tried to invent something?

81.  If you could change your name to anything, what would you pick?

82.  If I said you could date other people, would you?

83.  What do you think I’d say is your most attractive quality?

84.  What’s your favorite way to show affection?

85.  What’s your favorite way to receive affection?

86.  What’s one thing you think makes our relationship unique from everyone else’s?

87.  If you could change one thing about our relationship what would it be?

88.  If we could go anywhere together right now, where would you want to go?

89.  What do you think is your biggest strength in this relationship?

90.  What’s your biggest weakness in this relationship?

91.  Who do you think is the most affectionate in our relationship?

92.  How do you think we both have changed since we first started dating?

93.  What about us both is exactly the same since we first started dating?

94.  What’s one thing I do that makes you feel good, that you wish I did more?

95.  What’s one thing about your life you would never change for someone else, including me?

96.  What about us do you think works well together? How do we balance each other out?

97.  What’s one thing you hope happens in the future of our relationship?

98.  What does love mean to you?

99.  What do I mean to you?

100.  What does this relationship mean to you?

101.  What makes you feel the most loved?

102.  What’s your dream date night?

103.  What’s your favorite romance movie?

104.  What’s your favorite meal to cook for date night?

105.  What kind of music puts you in the mood?

106.  What’s the number one thing that you think makes a relationship last?

107.  If I gave you $ 1000 and asked you to get something for us, what would you get?

108.  What cute name would you want to give me?

109.  What do you love most about me?

110.  What setting do you think makes the perfect date night atmosphere?

111.  What physical action or gesture do you find romantic?

112.  Who do you think makes a great example of a relationship and why?

113.  What’s your favorite way I touch you?

114.  If you could travel anywhere in the world with me with no monetary restrictions, where would we go?

115.  What song do you think of when you think of me?

116.  Is there anything about me you might not know but want to know?

117.  When and what was the first moment you knew you were in love with me?

118.  What’s your most favorite outfit I wear?

119.  What’s your favorite restaurant for date night?

120.  What could I do to improve our relationship?

121.  What about me first attracted you?

122.  What’s been one of the funniest times we’ve had together?

123.  What do you say to others when you talk about me?

124.  Why do you think we met each other?

125.  What do I do that helps you calm down?

126.  Is there anything I can do to help you feel more special?

127.  What’s one thing you want to do with me that we haven’t done yet?

128.  When are you the happiest with me?

129.  What great adventures do you think we’ll achieve in the next 5 years?

130.  What values do you think are most important in a relationship?

131.  Is there anything you’re afraid to accomplish that I can help you with?

132.  Is there anything you’d like me to be willing to change?

133.  Has anything surprised you about our relationship?

134.  What can I do to encourage you on a regular basis?

135.  What strengths do you see in our relationship?

136.  What weaknesses do you see in our relationship?

137.  What goals would you like to set for our relationship?

138.  What do you think is most important for communicating in our relationship?

139.  Would you rather receive the most amazing massage you’ve ever had in your entire life from me or have me pour my heart and soul out in the most beautiful poem you’ve ever read?

140.  What moment would you want to relive again and again?


Fun Questions To Ask Your Boyfriend

If you want to freshen up your relationship, we have put together a list of fun, enjoyable questions to ask your boyfriend. Every relationship at some point needs some sort of spark.

These questions will offer you and your partner an exciting way to enjoy yourselves while you get to know each other. Choose from the options below to drive your relationship to the next level!

1.  Which celebrity are you rather certain would be your BFF if you ever met?

2.  What’s the longest you’ve ever gone without sleep?
…without a shower?
…without clean underwear?

3.  What’s your biggest pet peeve?

4.  What is one superpower you would hate having?

5.  What food do you wish you cook like a world-class chef?

6.  What’s the last book you read and really enjoyed?

7.  What is one song that can always pull you out of a bad mood?

8.  What’s the worst movie you’ve ever seen?

9.  What’s something you misunderstood as a child and only realized much later was wrong?

10.  If you had to, what would you change your name to?

11.  Which color do you most identify with?

12.  If you were in charge, what holiday would you create?

13.  What fast food place are you ashamed to admit you, love?

14.  What was the strangest thing you ever did as a child?

15.  What’s the funniest lyric you’ve ever misheard?

16.  Which sports team would you rename, and to what would you rename them?

17.  Have you ever been in a stage production?

18.  Which game show do you think you’d definitely win?

19.  Is there a game you’d like to play that we haven’t tried before?

20.  What would you say is your worst trait?

21.  What would you say is your best trait?

22.  Can you describe your ideal vacation?

23.  What’s something that scares you?

24.  What is your perfect brunch order?

25.  What’s your Patronus?

26.  Which sandwich topping do you most identify with?

28.  In your childhood, what’s a food that you used to really love that you can’t believe you ate?

29.  What ad is super irritating to you?

30.  If you had to run for public office, what would you run for?

31.  What are one or two things you don’t understand about the generation after yours?

32.  What are one or two things you don’t understand about the generation that precedes yours?

33.  If you could only watch one sport and all others were banned for the rest of your life, which sport would you choose?

34.  What are your thoughts on pickled foods that aren’t cucumbers?

35.  Can you name one thing that you know is kind of ridiculous, but you’re adamant about and will argue over it to the death?

36.  Do you have a favorite flower or plant?

37.  What kind of pet would you love to have?

38.  Do you consider yourself a spender or a saver?

39.  What was your dream job when you were a kid?

40.  Are you a mountain person or a beach person?

41.  What’s the strangest dream you’ve ever had?

42.  Would you get a tattoo? Or, what’s your plan for your next tattoo?

43.  Which celebrity chef would you want to learn from?

44.  Is there anything that you to do to reduce stress?

45.  What are your three favorite colors?

46.  Do you have any wardrobe accessories you can’t live without?

47.  What’s something you’ve tried that you thought you’d hate but actually ended up liking?

48.  What’s your favorite emoji?

49.  What’s the goofiest knock-knock joke you know?

50.  Choose one and explain your choice: dog, cat, fish, or bird?

51.  If you could become a master artist, why type of art would you make?

52.  Which country would you like to visit together?

53.  What’s your favorite thing for me to wear?

54.  What goes on your favorite ice cream sundae?

55.  What piercings would you like to get?

56.  What’s your favorite season?

57.  What’s your favorite seasoning?

58.  What is your dream car?

59.  Did you ever have a favorite childhood toy?

60.  Do you have a preferred kind of noodle for your mac & cheese?

61.  What is one thing you’ve done that you’re most proud of?

62.  What’s your favorite dessert?

63.  If you could relive one day of your life, which day would you pick?

65.  Would you rather have photos or paintings hanging the walls of your house/apartment?

66.  Have you ever won a TV or radio contest? If you did, what did you win?

67.  Which social media platform is your favorite?

68.  Which Social Media platform is your least favorite?

70.  Which would you rather watch: The Today Show, Good Morning America, or CBS This Morning?

71.  What’s your favorite spa treatment? Or what kind of spa treatment do you most want to try?

72.  Should people unwrap gifts slowly or quickly?

73.  What’s your biggest complaint about the country?

74.  What is one thing you think could make our relationship stronger?

75.  Are there any festivals or events you’d like to go to the next time we’re together?

76.  What’s your favorite thing to see at a circus?

77.  Which amusement park ride would you head for first?

78.  What type of beverage do you drink most in a day?

79.  What’s one skill you’d like to learn or improve?

80.  What are your top five snack foods?

81.  Would you rather read the book than seen the movie, or see the movie and read the book?

82.  What’s the most recent comedy special you’ve seen?

83.  Is there a TV show you’re hooked on?

84.  How do you feel about mixing Play-Doh colors?

85.  What’s the longest you’ve ever worn a pair of jeans without washing them?

86.  What’s your preferred cut of underwear?

87.  What was your favorite fairy tale growing up?

88.  For what occasion did you wear the fanciest clothes you’ve ever worn?

89.  If you could meet one person today, living or dead, who would you choose to meet?

90.  What song comes on the radio and makes you feel all the feels?

91.  Which holiday is your favorite?

92.  What is your most prized possession?

93.  Crossword, word search, or sudoku?

94.  What is a project you’d like to make with your own hands?

95.  What is one commonly held belief that you just don’t buy into?

96.  What is the most hideous fashion fad that you’ve ever seen?

97.  What’s the first you’re going to do the next time we see each other?

98.  What would you do if you returned from work and found me in the shower?

99.  What game did you love most while growing?

100.  What game would you never try out even if I gave you $100?

Serious Questions To Ask Your Boyfriend

One of the ways to test your boyfriend’s intellectual capacity is to ask deep questions. Of course, you don’t want to be with a dummy who is unable to sustain impactful conversations.

Asking your boyfriend serious questions helps you assess his worldview, see topics that stimulate him, as well as learn his views on controversial topics. Here are some suggestions of serious questions to ask your boyfriend.

1.  If you could fix one world problem, what would it be?

2.  If you could live in any era, which would it be and why?

3.  What advice would you give to a person who is just graduating high school?

4.  If you could have chosen your own name, what would you have picked?

5.  If you became famous, would you enjoy the limelight or miss your privacy?

6.  If you had $200 to spend on something special just for me, what would you buy?

7.  If you had three wishes, what would they be?

8.  If you were told you have a terminal illness, how would you take the news?

9.  If you only had a week left to live, what are some things you would do?

10.  Would you sacrifice yourself for a stranger?

11.  If a family member needed a kidney and you were the only match, would you give one up?

12.  You suspect that your neighbors may be abusing their child, do you mind your own business or call the police?

13.  If I went missing, my body never recovered, would you move on or devote your life to looking for me? If you did move on, how long would you wait?

14.  If you could invite 3 people to dinner, who would they be?

15.  If you could live till you were 90 and either have the mind or body of a 30-yr-old, which would you choose and why?

16.  If you could wake up tomorrow and have gained one ability, what would it be and why?

17.  If a crystal ball could tell you the truth about your life, me, or the future, what would you want to know?

18.  If you could live anywhere, where would you live?

19.  Which one fits you better? “Live for the moment”, or “Save the best for last”?

20.  What’s your favorite thing about yourself?

21.  If you could change anything about yourself, what would it be?

22.  Do you prefer going out or staying in?

23.  Would you consider yourself an externally motivated or internally motivated person?

24.  How do you deal with failure?

25.  Do you put more attention to the people around you or the things around you?

26.  When things break, do you prefer to fix them or replace them?

27.  Would you consider yourself materialistic?

28.  What would you consider a perfect day?

29.  What would be your perfect date night?

30.  What are some things that offend you?

31.  What is one thing that you cannot start your day without?

32.  If you’re stressed out, what helps you wind down?

33.  When you die, do you want to be buried or cremated? Why?

34.  What inspires you?

35.  Would you consider yourself an optimist, pessimist, or realist?

36.  We notice an old man living out of a shopping cart behind a grocery store. What is your first thought about him?

37.  Someone calls me something horrible. Do you let me fight my own battles, or jump in and defend me?

38.  Do you think it’s okay to have a close female friend at work?

39.  What are three things you are willing to splurge on for yourself?

40.  What’s something that no one else knows about you?

41.  Do you ever rehearse a phone call beforehand?

42.  When did you last sing to yourself? To someone else?

43.  What are you most thankful for?

44.  Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?

45.  What do you most fear about getting older?

46.  Have you ever done something you regretted?

47.  Where do you see yourself in five years?

48.  When was the last time you shed a tear?

49.  What is a tradition you did as a child that you want to do with your kids someday?

50.  What are some things in life that you had to learn the hard way?

51.  Do you have any dreams from childhood that you can vividly recall?

52.  What were your childhood aspirations, and how have they changed?

53.  How do you picture your life when you’re 60?

54.  What is your most terrible memory?

55.  How have you changed the most since you were younger?

56.  In what areas do you want to change the most?

57.  When was the first time you were in love?

58.  When was the first time you said I love you?

59.  Is there any book that changed your life?

60.  What is your biggest insecurity?

61.  Is there anything you’re ashamed of?

62.  Is there anything you wouldn’t want your family to know?

63.  If you could change anything about the past, what would it be?

64.  Why do you think the divorce rate is so high nowadays?

65.  What do you think is the biggest flaw of the welfare system?

66.  If you were running for president, what are three key things you would include in your campaign?

67.  Are you pro-choice or pro-life?

68.  How do you feel about genetically modified food?

69.  What is one thing that you feel would make any small business owner more successful?

70.  What invention do you think has done the most for the human race?

71.  Should children be allowed to have cell phones?

72.  Do you think a person’s outward appearance says anything about who they are as a person?

73.  How important do you think it is to do well in school?

74.  Would you consider yourself proud to live in this country?

75.  Is there anything too serious to be joked about?

76.  What is your position on premarital lovemaking?

77.  What do you look for most in a spouse?

78.  What religious/spiritual views do you have and why?

79.  How important is it for you to save money?

80.  How important is it for you to invest money?

81.  How important do you think making out is in a marriage?

82.  If one of us had to move far away, would you be able to handle a long-distance relationship?

83.  What is one thing that can destroy a relationship and never be forgiven?

84.  Do you want to have kids someday when you meet the right person?

85.  Do you think it’s more important to work or spend time with family?

86.  What are three key elements in every successful relationship?

87.  Do you think people can or should be friends with their exes?

88.  Do you believe emotional ‘cheating’ is just as bad as real cheating?

89.  What do you think of open relationships?

90.  Are you looking for commitment?

91.  What was your first impression of me?

92.  Would you surprise me with an expensive gift, or would you consult me before spending the money on it?

93.  Would you rather I be good in the kitchen or good in the bedroom?

94.  What do you think is more admirable, a stay-at-home mom or a career-driven mom?

95.  Would you rather leave a big impact on the world or a big impact in your family?

96.  What song do you think best fits our relationship?

97.  Do you think a proposal should be a grand public display or a private intimate moment?

98.  If we had children, what features would you want them to get from you and which from me?

99.  What’s something you could never compromise about?

100.  Do you forgive and forget or forgive and remember?

101.  If you had kids, what would be your biggest hope and the biggest fear for them?

102.  What is one area in your life where you feel like something is missing?

103.  Do you think your significant other can be both your best friend and your lover?

104.  Do you think it’s better to have the worst house in a nice neighborhood or the best house in a bad neighborhood?

105.  Is life anything like you had pictured it would be growing up?

106.  Would you rather have a life full of love or a life full of money?

107.  Can a positive outlook make any situation better?

108.  Do you think children are more of a blessing or a burden?

109.  If I was giving birth to our child and complications arose that meant only one of us would make it, who would you save?

110.  What would you want said about you after you die?

111.  If you could go back in time to give advice to your younger self, what would you say?


Questions To Ask Your Boyfriend To Test His Love

How deep does his love for you go? Is there a special person in your life that you want to connect with on a deeper level?

Do you want to see if your boyfriend truly loves you, if he is still trying to find his feet around relationships, or if you are just a phase he is going through? The questions to ask your boyfriend in this section have been specially arranged to give you the answers to these and many more.

1.  What is it that you love about me the most?

2.  If you could change anything about me what would it be?

3.  What color do you think suits me best?

4.  How’s my hair looking today?

5.  Do you prefer me with makeup or looking natural?

6.  Do you remember how we first met?

7.  How did you get me to fall for you?

8.  Did you imagine then… we would be where we are today?

9.  Are you convinced I am the one for you?

10.  Was is it, love, at first sight for you?

11.  What is it that makes us work the most do you think?

12.  Do you think we could improve on our love?… If so what do you think it would be?

13.  If there’s one thing you could do for me, or I could do for you what would it be?

14.  On a scale of 1 to 10, how much do you love me?

15.  What make’s our love different to all the rest?

16.  What’s your ideal date? Or would you rather remain indoors with me?

17.  What’s my favorite romantic spot for us?

18.  If could go anywhere.. where would it be?

19.  What’s your favorite food?

20.  Do I like milk in my tea/coffee?

21.  Where do you want to take me for dinner this weekend?

22.  Do you think we need to try something new?

23.  Shall we start a hobby together?

24.  Would you like to meet me for a drink after work?

25.  Would you like to watch a movie with me all day?

26.  What’s your ultimate bedroom fantasy?

27.  What’s your favorite form of sensual pleasure?

28.  Is there a feature about me that turns you on straight away?

29.  Where do you like me to kiss you?

30.  Do I like wearing underwear?

31.  Where shall we go on our next holiday together?

32.  Do you see yourself spending the rest of your life with me?

34.  Do you want to start a family together one day?

35.  What would you like to accomplish from life?

36.  How are you feeling about our relationship?

37.  Did you think about me at work today?

39.  Do you want me to put some music on?

40.  Would you like me to accompany you to the gym?

41.  Would you prefer to read, watch a movie or just be with me?

42.  If you could start a hobby with me, what would it be?

43.  What are you most afraid of happening to us?

44.  What have your other relationships taught you before now?

45.  Would you like me to give you a massage?

46.  Would you like me to make your lunch for work tomorrow?

47.  Would you like me to press your shirts for you?

48.  How deep would you honestly say your love for me goes?

49.  What’s one thing we could change about each other that could help us move forward and understand each other better?

50.  Have you loved another more than me before?


Cute Romantic Questions To Ask Your Boyfriend

If you want to bond with him in a way that makes you inseparable forever, I suggest you try these cute questions to ask your boyfriend. You will certainly get to discover aspects of him you never knew about.

1.  Which would you pick between me and a box of gold?

2.  What is the first thing that comes to mind in the morning when you wake up next to me?

3.  Do you miss me when we’re not together?

4.  Would you shout my name to the world from the biggest skyscraper?

5.  Do you think that there is a special reason why we met?

6.  Is there anything about me that inspires you to do things differently?

7.  Is there a song that reminds you of me when you’re listening to it?

8.  How many times did you want to kiss me before our “official” first kiss?

9.  Would you kiss me on the forehead?

10.  Do you find me cute?

11.  If only one cookie remained, would you give it to me?

12.  What is the cutest thing about me?

13.  Does it make you feel good when I tell you what a gentleman you are?

14.  How do you feel when I say to you: ‘I love you‘?

15.  Do you find me pretty?

16.  Do you think I look cute even when wearing tomboy outfits?

17.  Do you really mean it when you say you love me?

18.  Do you have a pet name for me?

19.  What’s something I do (that I don’t realize I do) that you love?

20.  What is a silly thing about me that you love?

21.  Would you ever write a poem/story about me?

22.  Do you still get butterflies when we’re kissing?

23.  How do you feel when I send you a text message?

24.  Have you ever daydreamed about me?

25.  What is your favorite dream that involved me?

26.  Do I inspire you to become the best version of yourself?

27.  Do I look cute while being mad at you?

28.  If we are watching a scary movie, can you hug me when I get really scared?

29.  Would you take my hand to dance, even if we were the only ones on the dance floor?

30.  Is there any flower that reminds you of me?

31.  Would you ever want to lie on the grass and watch the stars with me?

32.  What outfits do you like the most on me?

33.  When you’re alone, do you ever imagine that I’m there next to you?

34.  What’s the craziest thing you would do for me?

35.  Has our relationship influenced you to change in any way? How?

36.  Has been with me helped you learn about yourself more?

37.  Do you like the feeling of falling in love with me?

38.  What is the one thing you’re really dying to do with me? Or one experience you would like to share with me?

39.  What is your favorite thing about us as a couple?

40.  What is your favorite color to see on me?

41.  When did you first realize that I like you?

42.  Could you imagine your life without me in it?

43.  Did you find winning me over to be hard or not? How so?

44.  What is the best compliment you have ever received from me?

45.  How many times did you think about inviting me on a date before you actually invited me?

46.  How would you describe me in one paragraph?

47.  What is your favorite nickname of mine?

48.  What do you consider to be the most irresistible part of a woman?

49.  Can I call you when I feel like hearing your voice?

50.  Do you trust me with your whole heart?

51.  Does it make you smile when I send you a text message?

52.  Would you stay in a long-distance relationship with me if we had no other choice?

53.  Would you meet my family?

54.  If you could describe my personality in 5 words, what would they be?

55.  How would you describe the feeling of being in a relationship with me?

56.  Is there anything that you don’t like about me?

57.  Do you see yourself with me in the future?

58.  Did anyone give you advice on how to ask me out on our first date?

59.  How do you feel about holding my hand in public?

60.  Would you kiss me when we’re in public?


61.  If I was scared, would you hold my hand?

62.  Do you find me the kind of girl you’d take home to your parents?

63.  How do you feel when I touch your body/face?

64.  Do you like when I massage you?

65.  Where is your favorite place to chill with me?

66.  Would you take a break for one week from your favorite hobby to spend it with me?

67.  Would you introduce me to your family?

68.  What is your ideal type of movie to watch with me?

69.  Have you ever been in love before me?

70.  When did you decide you wanted to introduce me to your friends?

71.  What are the traits of a healthy relationship?

72.  What did you enjoy about being single that you would like to keep in our relationship?

73.  Is there anything you would like to change about us as a couple?

74.  Is there anything you’re afraid to tell me?

75.  Is there anything you would want to know about me, but you’re afraid to ask?

76.  What was your overall first impression of me when you first saw me?

77.  Do you remember some of the details of our first date?

78.  Which do you prefer more—kissing in the dark, under the Sun or in the rain?

79.  What is your favorite place for making love?

80.  Do you like to cuddle?

81.  Would you rather hug me for 6 seconds or kiss me for 2 seconds?

82.  Are you happy with me?

83.  Were you nervous/anxious before our first kiss?

84.  When did you decide you wanted us to be officially together?

85.  Are there any flaws that you like about me?

86.  How does your ideal date look?

87.  What is the best part about being in a relationship and why?

88.  Do you ever talk about me when you’re spending time with your friends?

89.  If one of your friends or family members told you to break up with me because he/she didn’t like me, would you?

90.  Would you be embarrassed if I called you by a cute name in front of your male friends?

91.  If you caught another guy flirting with me, what would you do or say?

92.  Do you prefer a date watching Netflix and chill alone, or going out at the movie theater?

93.  Do you think your friends and family (will) like me, too?

94.  Where would you want to go on vacation with me and why?

95.  Would you rather go on a road trip with me or with your friends?

96.  What is your definition of an ideal partner, and do I possess any of those traits?

97.  Have you ever been deeply hurt or disappointed in someone?

98.  Do you feel relaxed with me?

99.  What’s your biggest fear for this relationship?

100.  What’s your biggest deal-breaker during a date?

101.  What is your favorite memory so far of spending time with me?

102.  When did you fall in love with me?

103.  When did you first realize you loved me?

104.  Do you remember the day of our first date?

105.  Would you ever write a romantic love song for me?

106.  If I were to make you breakfast in bed, what would you want it to be?

107.  Would you ever risk your life in order to save mine?

108.  Do you believe some people are destined to be together?

109.  How would you describe our first kiss/love making?

110.  What is your favorite romantic place ever?

111.  Do you think we’re soulmates?

112.  What are the 3 reasons you like/love me?

113.  Do you believe that love can conquer anything?

114.  Would you carry me in your arms if my feet hurt?

115.  Are we both lovers and best friends?

116.  If we could spend our next weekend anywhere we want, where would it be?

117.  Would you prepare a romantic dinner for me, and if so, what would it look like?

118.  How do you show your love to someone you care about the most?

119.  What is the one thing that you like about me the most?

120.  If you had only 2 minutes with me, what would you want to do?

121.  What does it feel like to you when we’re lying next to each other?

122.  What are you usually thinking about when we’re kissing?

123.  What is your favorite body part of mine?

124.  Where do you like to kiss me the most?

125.  Where is your favorite place to be kissed?

126.  How does it feel to kiss me on the wrist?

127.  Do you like kissing me on the neck?

128.  What is the first thing that comes to mind when I’m calling you?

129.  What do you enjoy more – cuddling or kissing with me?

130.  Do you like seeing me in dresses?

131.  Would you notice that I want to make love to you without me telling you so?

132.  What’s something that will make me fall in love with you instantly?

133.  What will you do if I suddenly kissed you right now, right here?

134.  Aside from being hot all day, what do you do for a living?

135.  What do you wear to bed (if anything at all) when you sleep?

136.  What would you do if you woke up and suddenly found me lying on your bed next to you?

137.  What kind of underwear do you think I’m wearing right now?

138.  What was the happiest moment of your life to now?

139.  What helps you persist when you feel like giving up on something?

140.  Do you like reading romantic poems?

141.  What are 3 situations that can always make you cry?

142.  Do you have a secret that you haven’t told anyone before?

143.  Have you ever cried while watching a sad movie?

144.  When did you have your first kiss?

145.  Do you have a celebrity crush?

146.  When do you feel respected the most?

147.  What is something you’re nostalgic about?

148.  Do you like meeting new people?

149.  What is the stupidest thing you’ve ever done?

150.  What is the best gift you’ve received for your birthday?


As much as you love asking your boyfriend some serious questions to find out what he’s all about, a long list of deep questions might be draining.

This is why I recommend mixing up the serious questions with some fun and juicy ones to keep things light and interesting. Also, ensure you set the mood for the session so that it doesn’t turn out tedious instead of exciting.


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Author: Relationship Culture

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