Questions to Ask Your Boyfriend: 130 Fun, Deep and Spicy

The best questions to ask your boyfriend are ones he has never been asked, about things he actually cares about. Below are 130 of them, sorted by mood: fun, deep, sweet, serious, spicy and long distance.

The list is only half of it. The other half is what you do when he shrugs and says "I don't know," or gives a great answer you forget by Friday. That part comes after the questions.

Start by choosing the right set for the moment:

The "how many" column is practical advice, not a research finding. Fewer questions with real follow-up almost always beat a long list read out loud.

Table of contents

1. Fun questions to ask your boyfriend
2. Deep questions to ask your boyfriend
3. Sweet questions about the two of you
4. Serious questions about your future
5. Spicy questions to ask your boyfriend
6. Questions to ask your long distance boyfriend
7. Guess his answer before he gives it
8. When he answers with one word
9. What to do after he answers
10. Questions that backfire

Fun questions to ask your boyfriend

Fun questions work because they have no wrong answer and nothing riding on them. They also tell you more than they seem to. How someone argues for the best sandwich says a lot about how he argues for anything.

1. What is a hill you will die on that nobody else cares about?
2. What is the most useless skill you are proud of?
3. If you had to eat one fast food menu for a year, which one?
4. What would your wrestling entrance song be?
5. What is the worst haircut you have ever had, and who is to blame?
6. Which fictional character do you think you would genuinely be friends with?
7. What is a movie everyone loves that you secretly think is boring?
8. If our life were a sitcom, what would it be called?
9. What would you do with a completely free Tuesday and no phone?
10. What is the pettiest thing you have ever done?
11. Which animal would be the most terrifying if it were the size of a horse?
12. What is your most irrational fear?
13. What did you believe as a kid that turned out to be completely wrong?
14. What is the weirdest thing you have ever googled?
15. If you could instantly be an expert at one hobby, which one?
16. What would you name a boat?
17. Which celebrity would you want to swap lives with for one week?
18. What is the best meal you have ever eaten, and where were you?
19. What is a smell that instantly takes you back to childhood?
20. If you were a ghost, who or what would you haunt?
21. What song do you know every word to but would never admit in public?
22. What is the most money you would pay for the perfect burrito?
23. If you could add one rule to every sport, what would it be?
24. What is your go-to karaoke song, and do you actually sing it well?
25. What would your dream job be if money did not matter at all?
26. What is the strangest compliment you have ever received?
27. If you could only wear one outfit forever, what would it be?
28. What is a food combination you love that other people think is gross?
29. If our pet could talk, what would it complain about first?
30. What is the most embarrassing thing in your camera roll right now?

If he likes a quick back-and-forth, the flirty questions to ask your partner take the same playful energy and add a little heat.

Deep questions to ask your boyfriend

Deep questions ask for something he has not said out loud before. They are slower, so ask fewer and leave room for silence. Each one below has a short note on what it tends to open up.

31. What is something you are proud of that nobody really congratulated you for? The achievement he quietly carries.
32. What did you need more of growing up? Often the key to what he needs from you now.
33. When do you feel most like yourself? Where his energy comes from.
34. What is a belief you held strongly five years ago that you have since changed? How he updates his mind.
35. What are the signs you are stressed that other people miss? Your early warning system.
36. How do you want to be comforted when you are having a bad day? Instructions you will need later.
37. Who shaped the way you think about love? His model of a relationship.
38. What is a fear you have never said out loud? Only if the first few went well.
39. What makes you feel respected? For some people this matters as much as feeling loved.
40. What is something you wish people asked you about more? A shortcut to his favorite topics.
41. When did you last feel really lonely? Gentle. Do not rush the answer.
42. What does a successful life look like to you, apart from money? His real scoreboard.
43. What is the best advice you ignored? Honest and a little humbling.
44. What part of your personality took you the longest to accept? Self-acceptance, in his words.
45. Is there a friendship you miss? Who he has lost touch with, and whether he wants them back.
46. What do you think you are still learning about yourself? Where he is growing.
47. When you feel hurt, do you want to talk right away or have space first? Saves you both a lot of misread silences.
48. What is something you are afraid I would think less of you for? Handle the answer with care.
49. What moment changed the direction of your life? Usually a story you have not heard in full.
50. What makes you feel useful? A need that people rarely name.
51. What would you tell your 16-year-old self? Softer than it sounds.
52. What are you most grateful for this year? A good place to end a deep round.

Sweet questions about the two of you

These are about us, not about him. They are the easiest deep questions to answer because many people enjoy telling the story of how they fell for someone.

53. When did you first realize you liked me more than as a friend?
54. What did you think of me the first time we met?
55. What is a small moment between us you think about more than I would guess?
56. What is something I do that makes you feel loved?
57. What is your favorite photo of us, and why that one?
58. When do you feel closest to me?
59. What is a habit of mine you secretly find cute?
60. Which of our dates would you repeat exactly as it happened?
61. What is something you have learned from me?
62. What song reminds you of us?
63. What is one thing about us you never want to change?
64. When did you know you could trust me?
65. What is something you want me to know but have never found the right moment to say?
66. If you described our relationship to a stranger in three words, which three?
67. What is a tradition you want us to start?

Serious questions about your future

Future questions feel heavy when they arrive in a pile. Ask two or three at a time, on a calm day, and be ready to answer each one yourself first. If you are close to engagement, the questions to ask before marriage go deeper on money, family and legal paperwork.

68. Where do you see yourself living in five years?
69. What does a normal weekday look like for us in the future?
70. How do you feel about kids, and has that changed?
71. How were money and debt handled in your family growing up?
72. What would you want to do differently from your parents?
73. How important is it to you to live near your family?
74. What does commitment mean to you in practical terms?
75. How do you want us to handle disagreements?
76. What career risk would you take if you felt secure?
77. How much time alone do you need to feel like yourself?
78. What role do you want friends to play in our life as a couple?
79. How do you feel about pets, and how many is too many?
80. What does a good holiday season look like to you?
81. What is one thing you want us to save for?
82. If one of us got a great job in another city, how would we decide?
83. What does growing old together look like in your head?
84. What are you most looking forward to about our future?
85. What worries you most about our future, if anything?
86. How do you want us to check in when something feels off?
87. What is one thing we could start doing this year to get closer to that future?

Spicy questions to ask your boyfriend

Spicy questions work best late, in private, and with an easy way out. Agree on one rule before you start: either of you can say "pass" without explaining. Keep the talk about the two of you, not about past partners.

88. What was the first thing you found attractive about me?
89. What outfit of mine do you think about later?
90. Where is the most unexpected place you have wanted to kiss me?
91. What is your favorite way for me to touch you when we are not being intimate?
92. What is a compliment about your body you would love to hear more?
93. What is the most attractive thing I do without realizing?
94. What is a fantasy you have never told me about?
95. Morning or night, and why?
96. What do you want more of in the bedroom?
97. What is something you have always wanted to try but felt shy to ask about?
98. What is the best kiss we have ever had?
99. What text from me would ruin your concentration at work?
100. What is one thing I do that instantly puts you in the mood?
101. What is your favorite memory of us being intimate?
102. Slow and romantic, or spontaneous and a little reckless?
103. What is a turn-off you have never mentioned?
104. If we had a whole weekend alone with no plans, how would you want it to go?
105. What is something you want me to say more often?
106. What would make you feel more wanted by me?
107. Is there anything you would like us to stop doing, or do differently?

If you both enjoy this round, the spicy hot seat questions turn it into a proper game with rules for taking turns.

Questions to ask your long distance boyfriend

In a long distance relationship, questions do the job that shared evenings do for other couples. Words have to carry most of the closeness, so pick fewer and choose them well.

Three adjustments help. Check what time it is for him before sending something heavy, because a deep question at 1am his time gets a tired answer. Send the longer ones as voice notes, since tone is the first thing text loses. And save the most personal questions for a call where you can hear his pause.

108. What was the best and worst part of your day?
109. What did you see today that you wished I had been there for?
110. When do you miss me most during the week?
111. What is the first thing you want to do when we see each other?
112. What is a small, ordinary thing you are looking forward to doing together?
113. What part of long distance has been harder than you expected?
114. What part has been easier?
115. What helps most on the days you are running low on patience with this?
116. What is something about your city you want to show me?
117. How often do you want to talk, honestly, not just what sounds nice?
118. What would make our calls feel less like an update and more like a date?
119. What is a story you have been saving to tell me in person?
120. What does closing the distance look like to you, and when?
121. What should I send you on a bad day?
122. What is a new routine we could share even from far apart?

Question 117 is worth asking early. It is easy to drift into a calling schedule neither of you actually chose, and one honest conversation can reset it. There is more on that in this guide to long distance relationship communication, and if he likes a lighter ending to the day, these good night messages for him are built around time zones.

Guess his answer before he gives it

Say your guess out loud before he answers. It turns any question on this page into a game, and it shows you how well you actually know him.

That second part is less certain than it feels. In a 2011 study of 24 married couples, described in the University of Chicago's summary of the research, people sat with their backs to each other and tried to interpret ambiguous everyday phrases. Speakers expected their spouse to understand them better than a stranger would, and felt more confident they had been understood, yet the spouses were no more accurate than the strangers. It was one small lab task, not a measure of how well couples understand each other in daily life. The authors called it the closeness-communication bias: feeling close can make people assume understanding they have not checked.

The guess-first rule is a practical way to check it. It was not tested in that study. It simply puts your assumption on the table before his answer arrives, so the gap becomes a conversation instead of a silent misunderstanding.

Eight good questions for guessing:

123. What would you order at a restaurant you have never been to?
124. What is the one thing you would grab in a fire, after me?
125. What would you do first if you won a large sum of money?
126. Which of your friends do you think I like the most?
127. What is the most "you" way to spend a Saturday?
128. Which of my habits do you think I would find hardest to give up?
129. What would you cook if you had to impress my family?
130. What is the last thing that made you laugh out loud?

Keep score if you like. Whoever loses picks the next question. This is also how the How Well Do You Know Me game in FeelClose works: you both answer the same question, then each of you guesses what the other said before the answers are revealed.

When he answers with one word

A one-word answer is usually about timing or the question, not about you. Before deciding he does not want to talk, check which kind of short answer you got.

The common belief that men simply do not open up is weaker than it sounds. A 1992 meta-analysis of 205 studies covering 23,702 participants found women disclosed only slightly more than men on average, and the size of the difference varied a lot from study to study. The gap was larger when people were talking to women or same-sex listeners than to men or opposite-sex listeners, though with spouses, friends and family women still disclosed more. The data is old and describes averages, not your boyfriend. It does suggest a short answer is often worth a second try.

Two more things tend to help. Answer the question yourself before he does, because it shows how long an answer you are hoping for. And try asking side by side, on a walk or in the car, rather than face to face across a table. That is a practical suggestion, not a study finding, but many people find hard questions easier without eye contact.

If short answers are the pattern with every question, every time, that is worth a gentler conversation about how you both like to talk. A regular relationship check in can give that conversation a structure that does not feel like an ambush.

What to do after he answers

The question starts the conversation. What you do in the next thirty seconds decides whether it goes anywhere.

Ask one follow-up. In three studies of get-to-know-you conversations, people who asked more questions, particularly follow-up questions, were better liked by the person they were talking to. Speed daters who asked more follow-ups got more agreements to a second date. Those were conversations between strangers, not couples, so treat it as a strong hint rather than proof about relationships. A simple "What happened then?" or "Why that one?" shows you heard the first answer.

Turn toward what he says. The Gottman Institute calls small attempts to get a partner's attention "bids for connection." As the Institute describes in its article on bids, Gottman and Levenson followed couples up six years after observing them. Those still happily married had turned toward each other's bids 86% of the time, compared with 33% for couples who had broken up or stayed together unhappily. That is an observed difference between groups of couples, not proof that turning toward bids alone keeps a relationship together. An answer to a personal question is a bid. Put the phone down and respond to it.

Do something with it within a week. If he says being helped without asking makes him feel loved, do that on an ordinary Wednesday. If he names a friendship he misses, ask about that friend next month. Answers that lead nowhere teach him the questions were just entertainment.

Write the good ones down. Gottman uses the term love maps for the detailed picture you hold of your partner's inner world, and it only stays accurate if you keep adding to it. A note on your phone is enough. Quoting something he said a year ago shows you were listening.

Questions that backfire

Some questions sound curious but work as tests, and the partner being tested can usually tell. Four types to skip or handle carefully.

Questions about exes. "Who was your first love and why did it end?" can be fine late in a relationship when both of you raise it. Asked early, or asked to compare, it invites an answer that either hurts you or flatters you, and neither tells you much.

Cheating hypotheticals. "Would you ever cheat?" and "Why do you think people cheat?" produce the answer everyone knows is expected. If you are worried about something real, name the real thing instead.

Loyalty tests. "Would you still love me if I gained weight?" leaves him one correct answer to perform. These questions check for reassurance, and there is a better way to get it: ask for it directly. If you want playful questions with a catch, these trick questions to ask your boyfriend come with the answers written out, including what a green-flag reply sounds like.

Anything in the middle of an argument. A deep question during a fight is usually gathering evidence. Wait until you are both calm. When something does need raising, a gentle start-up, describing how you feel and what you need without blaming, is a better opening than any question on this list.

Start with three tonight

Do not try to work through 130 questions. Pick three: one fun question to warm up, one deep question, and one sweet question about the two of you to end on. Guess his answer before each one. Ask one follow-up. Then stop while you both still want to keep going.

If you would like a question already waiting for you each day, FeelClose sends both of you the same daily question. You each answer privately, and neither of you sees the other's answer until you have both replied, so nobody copies the other. For couples living apart, it also has a countdown to your next visit and one-tap nudges for the days when there is not much to say.