365 Deep Questions To Ask Your Boyfriend

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Looking for deep questions to ask your boyfriend? Want to create more interesting conversation, further strengthen your bond, and really get him opening up?… Regularly? Then you’ve come to the right place. See, this article isn’t a mix of different questions to ask your boyfriend. This is a list PURELY packed full of deep questions to ask your boyfriend. 

And, the best part? We’ve fully stocked you up! Uh huh. We have 365 deep questions here – giving you a question to ask every single day of the year.

For this reason, we haven’t broken them down into categories. Instead, each question flows on from one to another, focusing specifically on getting to know your boyfriend better.

Read it, save it, print it! Then ask one of these questions a day, every day for the next year.

By the end of it, you will feel so much closer to your partner. It will also mean you’re connecting on a deeper level every single day. Whats more – question time will be a fun, original added-extra to your relationship, that helps to keep it fresh, fun and exciting!

So this is going to be a real game-changer…

How To Ask Your Boyfriend Deep Questions

So when it comes to HOW to ask your boyfriend deep questions, you want to certainly make sure it doesn’t feel like an interview!

Make it casual, or go into it with genuine interest! You could also start the conversation off by sharing your thoughts on the topic, then switch it around to lead into his specific question.

The better you go about it, the more likely he is to genuinely open up. For this reason, picking your timing is also important…

When To Ask Your Boyfriend Deep Questions

If you want a deep conversation with your boyfriend, don’t ask these questions when he’s stressed, in the middle of something, or tired after a long, hard day at work.

Otherwise you won’t get the kind of response you want!

Instead, you want to ask your boyfriend deep questions during date nights – when it’s just the two of you having quality time together. Or when you’re snuggled up on the sofa on the evening, already chatting and relaxing.

Trust me – it makes a major difference to how engaged and responsive he will be!

365 Deep Questions To Ask Your Boyfriend

So without further ado, let’s jump into these deep questions to ask your boyfriend, shall we?

Remember – this isn’t a quiz! It’s a conversation starter! So with each question, be sure to share your own thoughts / feelings / answer to it too.

That way, you’re both getting to know each other better. It’s not one-sided and you’re able to build a stronger connection in all round. Agreed? Awesome.

So what have we got for you? Well, in no particular order…

Deep Questions To Ask Your Boyfriend

1) What kind of person do you want to be? I mean, what things are most important to you, as a person?

2) What things do you find most attractive in another person and why? Besides physical appearance.

3) What qualities do you admire most in another person, and why?

4) What kind of morals & standards do you (or do you want to) always live your life by?

5) What has shaped your morals, standards and beliefs? Where have these come / developed from?

6) How have your morals / values changed over the years? Let’s say in the last 10 years, 5 years, 2 years or 1 year even!

7) In what ways have you grown into the person you want to be, so far?

8) In what ways haven’t you grown into the person you want to be, so far?

9) What do you think are your biggest strengths and weaknesses as a person?

10) What’s holding you back / stopped you from being everything and all that you want to be?

11) How do you think a person truly reaches the point of full self-acceptance?

12) What do you think is fundamental to building ones self-confidence?

13) Do you think you have a full understanding and appreciation of yourself and your worth?

14) In what moments / times have you ever questioned yourself or your worth? And why?

15) What is one thing you will never put up with?

Let’s Keep Them Coming…

16) Are there any inspiring quotes or mottos you try to live your life by?

17) What are some of the best pieces of advice you’ve gotten from another person? And what about it, made it stick with you?

18) What things and qualities do you like most about yourself?

19) What would you change about yourself if you could? 

20) Who inspires you to become a better person? (In whatever way.)

21) What things do you think make you a genuinely good person?

22) What are you most thankful for in your life? And how often do you stop to appreciate it?

23) What has been the biggest benefit in disguise in your life?

24) Do you have any celebrity / famous role models in your life? And what’s the story behind that – how and why did you come to admire them?

25) How about personal role-models, from people you know? Who do you look up to the most?

26) When you need some advice, who is the first person you turn to?

27) Is there anything you think that I (or others), would change about you?

28) Have you ever felt like you’re not good enough for me? If so – why / why not? (Remember to tell them that they are MORE than good enough for you! But it’s good for them to open up…)

29) Do you ever / have you ever, felt like you’re trying to be someone you’re not? What kind of pretence was you putting on and why? And again – where was it coming from?

30) Do you think you’re easily influenced by other people? And if so – in what ways?

Deep Questions To Ask Your Partner

Deep Questions To Get To Know Your Boyfriend

31) How well do you think you know yourself? And what things about yourself are you still trying to figure out?

32) If you could live in someone else’s body for a day, who would it be and why?

33) If you had unlimited confidence – what things do you think you would do, which you wouldn’t without?

34) In which moments / situations do you feel the most confident and why?

35) In which moments / situations do you feel the least confident and why?

36) Generally speaking, do you like the way you look? Do you feel confident about the way you look?

37) If you could change one thing about the way you look, what would it be and why?

38) Do you have many insecurities? Or is there anything that makes you feel particularly insecure? (This could be physical features, situations, memories – anything at all!)

39) Do you hide your insecurities? If so – how? And how well, do you think? Plus, why?

40) Are there any situations that make you feel vulnerable? And what does this feel like to you?

41) What do you think would be the scariest situation to be in?

42) What’s your biggest fear? (And we’re not talking something like spiders. These are deep questions to ask your boyfriend remember – really get him opening up!)

43) How do you manage or deal with your fears? And how big of an impact do they have on your life?

44) How often do you find yourself worrying and what kind of things do you worry about?

45) Do you ever get anxious? In what kind of situations? And how do you deal with it?

Let’s Keep Them Coming…

46) Do you find it difficult to let your guard down, and let people in? Why? Or why not?

47) Do you find it hard to trust people? And what type of trust do you think is hardest to give?

48) How trustworthy do you think you are as a person? Honestly? 

49) And how much do you value trust as a whole?

50) Do you find it difficult or easy to communicate how you feel? And why do you think this is?

51) What do you think your strengths and weaknesses are, when it comes to communication?

52) And how do you think you could go about improving your communication?

53) Are there any things you wish that you could ask me or know about me? If so – nows your chance!

54) How difficult / easy do you find it to speak to me? Can you speak to me about anything / everything? Genuinely?

55) How good do you think you are at really listening to what another person is saying?

56) How do you typically respond when you’re faced with criticism? And why do you think this is?

57) Do you think you’re an argumentative person? And am I?

58) What things make you feel defensive? (If any.) And why is this?

59) Do you find praise or criticism to be more motivating?

60) What things do you think that you’re most protective over? And why is this important to you?

Deep Questions To Ask Your Partner

61) How jealous do you think you are as a person? And what kind of things make you feel jealous?

62) What inspires you to better yourself?

63) What advice would you give to others to stay determined?

64) What is the best way that we can motivate each other?

65) Do you feel like we both support each other? And in what ways?

66) What kind of things or situations make you angry?

67) What’s the angriest you’ve ever been?

68) How do you deal with your anger? And how well do you think you deal with it?

69) How well do you think you deal with conflict as a whole?

70) To what degree, do you think that conflict is “okay” and normal in a relationship?

71) Do you think you’re a confrontational person? In what ways? / Why / why not?

72) How often do you feel stressed? And what kind of things make you stressed?

73) How do you deal with your stress? And what giveaway signs are there that you’re stressed?

74) What kind of things or situations make you sad?

75) When was the last time you cried? And what did you cry about?

Let’s Keep Them Coming…

76) How often do you get sad? And do you think people know when you’re sad, the majority of the time? Do you think I always do? Why / why not?

77) When you feel sad, do you find it difficult to get out of this state?

78) How well do you think you deal with your emotions as a whole?

79) What things do you think you could do / try to develop your mental strength / stability?

80) Do you think you’re mentally / emotionally immature in any ways?

81) How good do you think you are at reading other people’s emotions? EG, can you tell when I’m not feeling 100%? If so, how?

82) How well do you think you can deal with other people’s emotions? And how much does it affect you?

83) What kind of things make you the happiest?

84) How happy do you think you are in your life right now? And does this measure up to how happy you want to be or think you could be?

85) What things would make you happier in your life right now?

86) And what have been your happiest moments in your life to date?

87) Do you think we all, are in control of our happiness, and how we feel? And to what degree?

88) What small things make you laugh or smile? (On this note – if you want to make your boyfriend laugh, break these deep questions up with some funny questions to ask your boyfriend too! See, you can still “lighten the tone” in between!)

89) How do you try to bring more happiness to other people’s lives? What do you do? And how much do you think about this?

90) What’s the best gift you’ve ever been given and why? (And no, he can’t say you… Although we all know you’re an absolute blessing! :P)

Questions To Bring You Closer To Your Boyfriend

Meaningful Questions To Ask Your Boyfriend

91) Is gift giving one of your love languages? What’s the most thoughtful present you’ve ever given someone? (Psst, if it’s an ex – leave it out! We don’t want to hear about that!)

92) Are there any things have you done (or often do) for others, which you wish more people would do for you?

93) What things do you think that people often take for granted? Or don’t appreciate enough?

94) What little things do you appreciate, more than most people know?

95) What’s one thing that no-one – even I – knows about you? Come on – spill the beans. Todays the day to open up!

96) What’s something that you are glad you will never need to do again in your life?

97) What are the most difficult times in your life that you’ve experienced? [If you already know the answer, talk in more depth about them… If he’s comfortable with this, of course.]

98) How did you get through the hardest times of your life? What did it take?

99) If you could get the chance to erase the pain from your life, would you? If not – why not?

100) How do you stay motivated through tough times? And what would you say your mental toughness is like?

101) What are some of the biggest lessons you’ve learnt through overcoming challenges / hardship?

102) Do you think you can take positives away from every and any situation? Let’s discuss / debate! (I know, sometimes you have to really dig deep with this one!)

103) Do you believe that everything happens for a reason, or do we just come up with explanations after the fact?

104) What things are you most proud of in your life to so far?

105) What’s one thing you achieved, that you never thought you could or would? And what did this then mean to you?

Let’s Keep Them Coming…

106) How proud do you feel that you make your family? And what do you think would / could make them prouder? (If that’s possible at all – I’m sure it’s not!)

107) If you could go back to a time in your life and do something different – would you? If so – what, when and why?

108) If you had to go back to a time in your life for a little while- which time in your life would you go back to and why?

109) What three events have had the biggest impact on who you are today? (Good or bad!)

110) What things do you hope to happen in the future? What “milestones” or “goals” are you looking forward to the most?

111) How good do you think you are at “adulting”?

112) What do you think is the best thing about being the age that you are? And the hardest thing?

113) Let’s take it back a little! What do you think was the best thing about being a child?

114) What special childhood memories will you always treasure, and why?

115) And are there any things you still miss now about being a child?

116) What was the scariest thing that ever happened to you as a child?

11) Do you have any bad / difficult childhood memories? Ones that you try to block out even?

Deep Questions To Ask Your Boyfriend

118) If you would be able to change anything related to the way you were raised, then what would you like to change?

119) If you get a chance to live in someone’s body for a day then who it would be and why?

120) Is there anything you wish you could tell your younger self? What would you say? And at what age?

121) What things do you think they should teach at school, which they don’t currently? (We’re talking life-skills based!)

122) Are there any lessons that you most definitely, learnt the hard way? 

123) What mistakes did you / have you, kept making, before you finally learnt?! 

124) Are there any things you’re still trying to learn / embed now? And what’s the hardest thing about doing this?

125) Do you have any regrets? Things you always wanted to do or wish you had / hadn’t done at a point in your life?

126) What do you think is the best way to deal with, or let go of, regrets?

127) When were you the most disappointed in yourself? And why?

128) And how hard / easy do you find it to let go of things?

129) What’s the best BAD decision that you’ve ever made? Yup, you heard right!

130) What’s one thing people told you to do / not to do, and you did the opposite – but are still thankful that you stuck to what you thought you should do / wanted to do, with it?

Let’s Keep Them Coming…

131) What’s the best decision(s) that you’ve ever made as a whole?

132) What are some of your biggest goals or dreams right now?

133) What’s one goal you have, that no-one knows about? (Something you’ve never really wanted to share, for whatever reason!)

134) How about some of your biggest goals or dreams for the future? (Say in 10, 20, 30 years time etc.)

135) How motivated do you think you are, in life, as a whole?

136) And what drives your motivation? What things are important to you and why?

137) Do you think we align in what we want, and the kind of future we aspire to have?

138) What’s your favourite thing about the work that you do right now?

139) 1What’s your least favourite thing about the work that you do right now?

140) Do you think you’ll always do what you do for work now? And do you truly want to?

141) Would you rather win the lottery and not be able to work at all, or work the perfect job and be more-than financially stable from it? Interesting one, I know! Remember to ask that all important “why” when going through each of these deep questions to ask your boyfriend, too!

142) If you had to change career paths, what would you do instead? And how would you feel about that?

143) If you could do any job in the world, what would you dream of doing?

144) How confident are you in your abilities, career wise?

145) What do you think are the most useful skill(s) you have? (Don’t be afraid to “big yourself up!”)

Questions To Get To Know Your Boyfriend Better

Different Conversation Starters

146) What about hobbies? Or more specifically – what do you enjoy the most out of the hobbies that you have? What do you “get out of them”?

147) Are there any hobbies that you’d like to try / pursue, or develop further even? If so, why haven’t you done so yet?

148) What does success mean to you? What would it look like in your life?

149) How important is it to you, that you’re successful? And why?

150) How much money do you think you would need to be happy and free?

151) What’s your thoughts / views on money as a whole?

152) What’s your thoughts / views on poverty? And is there any way we, as a society could better deal with it?

153) How about the environment? Any burning views or opinions on global warming, and what we need to do?

154) What’s one cause that’s especially close to your heart? And why?

155) What social issue would you most want to solve? And again – why?

156) If you were to write a book about anything, what would it be? Or what type of book do you think you’d be most likely to write, even?

157) What’s the best book, or one of the best books, you’ve ever read and why? How did it impact you?

158) If someone was to make a movie of your life so far – how interesting or exciting do you think it would be?

159) What’s one book, series or movie that you always remember, that had an impact on you in some way? And in what way did it affect you?

160) If you could go back in time to change one thing in your life, what would it be? And what do you think the effects would be? (Uh huh, this is a big one!)

Let’s Keep Them Coming…

161) If you could carve your future in any particular way, to make sure that it includes one certain thing – what would you pick?

162) What’s your thoughts on growing old? Is it something that scares yo at all?

163) How much do you think about, and prioritise, your health?

164) How much do you think about, and prioritise, your happiness?

165) Do you ever, or have you ever, tried journalling? 

166) Do you think mental health is something that’s talked about too much or not enough? And why?

167) What things do you think are not talked about enough in the media then?

168) If you could go back in time to change one thing in history, what would it be? And what do you think the effects would be? (Hard to say, I know – but it’s a good, deep, discussion piece!)

169) If you were to get into politics – what key issues would you want to tackle? And are there any new laws / regulations you already know you’d consider putting in place?!

170) How passionate do you think you are as a person? (Generally speaking, not when it comes to relationships!)

171) How opinionated do you think you are as a person? And is this a good or bad thing?

172) Do you think you spend the most time focusing on the past, future or present? And why?

173) Is there anyone who you still really miss in your life? Tell me about them!

174) Is there anything that still plays on your mind a lot, about your past?

175) How much do you value family time? What does it mean to you? Or what do you wish it would be like, if it isn’t quite everything you’d hope or want?

You’re Nearly Half Way Through!

176) What do you admire most about your parents?

177) Is there anything you don’t admire about them? Remember: this just stays between you and me.

178) Are you as close with your parents as you’d like to be?

179) What would you do if your parents or family, didn’t like your partner?

180) What do you admire most about your brothers / sisters? And again – is there anything you don’t admire about them?

181) Is there anyone in your life, who you wish you were closer to? And why aren’t you? What’s happened or what’s holding you / them back?

182) Is there anyone in your life that you lost touch with? And why? Do you miss them now?

183) What is the best memory that you have with someone you no longer speak to?

184) Have you ever held onto toxic people for too long? And what impact did it have?

185) What do you look for in a friendship?

186) Do you find it difficult to make new friends? Or keep onto old ons?

187) What’s been your longest lasting friendship and how are you two now?

188) Do you think people should grow apart? It’s a natural and normal part of personal growth?

189) What boundaries do you think you should have, and do you have, when it comes to friendships?

190) How do you think your friends would describe you?

Deep Relationship Questions To Ask Your Boyfriend

191) How do you think your family would describe you?

192) Okay, this will be interesting now then! How do you think I would describe you?

193) How would you best describe me?

194) How would you best describe the feeling of being in love?

195) What do you think is the best and worst thing about being in love?

196) Have you ever felt unrequited love? What was it like? How did it make you feel?

197) Have you ever been heartbroken? How did you manage to deal with it?

198) How many hearts do you think you’ve broken? And did you deal with those situations in the best way that you could?

199) What have been the biggest lessons you’ve learnt from past relationships, which made you a better partner to me, today?

200) What’s your thoughts on staying friends with an ex?

201) How would you feel if I was still seeing and speaking to my ex?

202) What things do I do, which make you trust me?

203) What things do you try to do, to build trust in the relationship?

204) Do you think we have any toxic relationship habits? And if so – how are we going to tackle them?!

205) How often do you feel lonely? And what kind of things / situations make you feel the loneliest?

Deep Questions To Ask Your Boyfriend

Let’s Keep Them Coming…

206) How loved do you feel, day to day? And what kind of things make you feel the most loved?

207) How do you think I give and want to receive love?

208) How much attention do you think you need? And what type of attention? From who? And why?

209) Do you think people really see you for you? And understand you?

210) How well do you think I understand you? 

211) How close do you think we are as a couple?

212) What do you think would bring us closer? Or how would you feel closer to me?

213) In what ways do you think we are similar and different? And how well does that work?

214) In what ways do I make you happy? And are there any things that I regularly do, that don’t make you happy?

215) How could I make you happier?!

216) What things are the most important to you in a relationship? And a partner, even?

217) In what ways do you think we bring our the best and worst in each other? (This is one of the tough relationship questions – but they’re important to ask!)

218) How do you think we have changed or grown since being together?

219) What kind of future would you love to picture for us? And how likely do you think it is to happen?

220) What sacrifices would you and wouldn’t you, make for this relationship? Or any relationship in general?

Deep Questions To Ask Your Boyfriend

221) What boundaries do you think you should have in a relationship? And do we have them, or not?

222) What should people in a healthy relationship get out of it?

223) What would you class as cheating, or being unfaithful in a relationship?

224) Why do you think that people do cheat, rather than just leave?

225) Why do people do things if they know it will hurt the person they love? Do you think they don’t love them as much as they should? Or it’s driven by selfish / irrational behaviour? Let’s discuss!

226) What does commitment mean to you?

227) What deal-breakers do you have in a relationship? (Try to think of ones that I may not actually know of!)

228) Are there any things that scare you about love and relationships? Are there any limiting beliefs about love that you know you have?

229) What’s your attachment style in a relationship? And how do you think that’s the same / different to mine?

230) What are you most excited about, for us? Both now, and in the near / distant future?

231) When do you think a person is ready for the next step in their relationship (e.g. moving in, getting married, having kids.) And do you think they always know for sure when they reach this point?

232) When do you think you’ll be ready for the next milestones in your life? 

233) What are some of the biggest lessons you’ve learnt about love and relationships so far, and how did you learn it?

234) What’s one thing that I’VE taught you?! Let’s hope it’s good and not bad!

235) What do you love and appreciate about me, that you don’t tell me enough?

Let’s Keep Them Coming…

236) What little things do you notice about me? That not everyone does?

237) What are some of your favourite, most treasured memories of us?

238) What key things do you think make a relationship last? And how are we going to make sure that WE last a life-time? (This is definitely one of the cute questions to ask your boyfriend!)

239) Do you believe in true love or love at first sight?

240) Do you think people are made for each other? (Because hey, we totally are… right?!)

241) What have your parents taught you or shown you (either directly or indirectly) about love and relationships?

242) What things do you hope will be the same / different to your parents relationship? (Obviously there’s some things you won’t know about, nor will want to know about! Kind of gross…!)

243) What kind of parent do you think you’ll be? (If you want to be a parent one day, or aren’t yet one!)

244) If you don’t want to have children – let’s talk more about that. (If you haven’t already.) Why don’t you want to have them? Have you always known you don’t want to have them? And how does it make you feel?

245) What things would you most want to teach your child, and how would you teach them it?

246) Are there any things that scare you when it comes to parenting?

247) What do you think are the pro’s and con’s of growing up in today’s world? Vs. 10 years ago, 20 years ago, 50 years ago, etc?

248) What’s your views on social media and the impact that that has on people?

249) How about the impact that advancements in technology, have had on our lives?

250) What do you think the world needs more of, to make it a better place?

Interesting Questions To Ask Your Boyfriend

251) What do you think the world needs less of, to make it a better place?

252) If you were to do something to try to spread more happiness in the world, what would you do?

253) Are there any injustices or issues, that make you really frustrated? And if so, how would you go about tackling them? (Let’s talk about that!)

254) What’s something horrible that we as humans have accepted, because that’s just how things are; but actually things don’t have to be that way at all?

255) If you could hear every time someone said something good about you or something negative about you, which would you choose?

256) What piece of culture or trend has died out, but you would like to see it make a comeback?

257) If you couldn’t fail – what’s one thing you would do?

258) If you only had one day to live, how would you spend it?

259) What about one month, one year, or five years to live? (Tricky question, I know!)

260) What event would you rather die than have to go through?

261) How would you most want to be remembered by others? (Don’t worry – it won’t come to any of this just yet! This is all just theoretical, remember!)

262) Do you want to leave a legacy at all? If so, what do you want to do to achieve this?

263) Would you rather be hated for standing by the truth or loved for telling lies? Honestly speaking.

264) What do you look froward to about getting old?

265) What do you think are the best habits that you have?

Let’s Keep Them Coming…

266) What do you think are the worst habits that you have? And are you trying to change them? What makes them difficult to change?

267) What’s your relationship like with food, and has it always been this way?

268) What’s the longest you’ve gone without sleep? And why?

269) What’s your thoughts on mindfulness? Or mindful living? And how much do you think you live by this?

270) What’s your thoughts on meditation? Good practice? Pointless practice? Or never done it before?

271) What things DON’T you believe in, that some / many people do?

272) And what things DO you believe in, that you know not everyone else does?

273) Are you spiritual or religious? And to what degree?

274) To what degree do you believe in second chances?

275) What things are and aren’t forgivable? In both relationships and in life?

276) What’s been the worst thing that you have been forgiven for? And can you truly say you learnt from it, or were able to put things right?

277) How often do you feel like you make mistakes?

278) How much do you focus on your personal growth? In which areas are you working on yourself? And how is it going?

279) Would you consider yourself more introverted or extroverted? And what do you like / dislike about this?

280) How do you feel in social situations? And how do you think you act, relating to that?

How To Strengthen Your Relationship

Deep Questions To Get To Know Your Boyfriend

281) How much space do you think you need, as a person? EG. If you’re in a bad mood, do you prefer to be left alone or have someone to cheer you up?

282) How do you feel when you’re on your own? And how would you feel if you had to stay on your own for a whole week / month… gee, let’s even go there… an entire year?! How would you cope?

283) What’s the craziest thing you’ve ever done in your life, and would you do it again?

284) What kind of things make you feel the most alive?!

285) Do you think you often “judge a book by its cover”?

286) Have there ever been times when you’ve judged someone – only for them to completely surprise you?

287) How often do you think you’re right when it comes to gaging a person’s character? And what’s the best example of when a person has just “proved you right”?

288) Where’s your most favourite place to go in the entire world?!

289) What’s one place you’ve always dreamed of going and why? Plus – do you think you’ll ever get there?!

290) What kind of things are on your bucket list? And why are they important to you?

291) What guilty pleasures do you have, which no-one knows about?

292) What’s your philosophy in life?!

293) Is there anything that you’ve learnt fairly recently that you probably should have known already? (But hey – better late than never, right?!)

294) When was the last time you had a gut feeling about something that turned out to be correct? And how about a time your gut feeling was wrong?

295) Have you ever acted a little “crazy” or out of character? What did you do? And what caused you to reach that point? (It’s okay – there’s no judgements here!)

Let’s Keep Them Coming…

296) Have you ever made an innocent mistake that actually had pretty severe or dramatic consequences?!

297) What’s on thing you would struggle to trust anyone with? (And if he says his Xbox, tell him to think again!)

298) How decisive or indecisive are you? And what kind of decisions do you struggle to make the most?

299) Do you think it’s better to make decisions based on your head or your heart?

300) What’s the biggest lie you’ve ever told? And why did you tell it?

301) How often do you find you lie? And how difficult / easy do you find it is to lie?

302) In what scenario, if any, is it okay to lie?

303) What’s the worst lie that someone else has ever told you? (No, he can’t go with Santa Clause. That’s bad, of course (ha!) but these are deep questions to ask your boyfriend, remember? So get him to dig deep with his answers too!)

304) What’s the difference between a lie and a secret? And do you think it’s okay to keep secrets if you’re “protecting a person?” Where’s the boundary with that?

305) When, if ever, is it okay to break the law?

306) How often do you go out of your way to help someone?

307) If you had an extra hour in the day, how would you spend it?

308) How fast / slow do you feel like time goes?

309) What’s your thought on outer space? Something that’s fascinating, or something that’s kinda scary?

310) How do you think that you could create the most significant, meaningful life?

Deep Questions To Ask Your Boyfriend

311) What things do you do, that add the most meaning to your life?

312) Would you rather acquire material items or experiences?

313) What thing(s) do you think make you unique?

314) How about our love story – what do you think is actually-pretty-special about that?!

315) Am I the kind of person you pictured yourself being with, before you met me?

316) What other sides do you think I bring out of you? Or other elements do I add to your life?

317) How often do you think about me? Or think about us?

318) What’s one thing you’re embarrassed to admit, when it comes to us and our relationship?!

319) Let’s switch it up – what’s the best conspiracy theory you can make up on the spot?

320) What conspiracy theories do you actually believe in? And why?

321) Why do you think we dream?!

322) What’s the worst dream you’ve ever had? And why did it shake you up so much?

323) What’s one thing you used to be scared of, but aren’t scared of anymore? And how did you overcome it?

324) What things do you think that women struggle to understand about men, and men struggle to understand about women? And why?

325) What do you think are the biggest differences between men and women, how they act, how they feel and how they’re wired?

We’re Flying Through Them Now…

326) What pressures do you feel as a man? Particularly ones which may not be quite the same for women?

327) As a whole, do you think it’s harder to be a man or a woman? And why?

328) If you could get into the mind of a woman, what things would you most want to know?

329) If you could mind-read either all of the GOOD things people think about you, or all the BAD things people think about you, which would you choose and why?

330) Do you think you’re more of a negative or a positive person? And in what ways?

331) Have you ever done something, categorically knowing it wouldn’t end well? If so, what? And why did you still do it?

332) Do you think you make more good or bad decisions in your life? And has it always been that way?

333) Do you think you’re more wild, or sensible? And why?

334) What do most people overestimate or underestimate about you?

335) What silly thing do you take a lot of pride in? Something that I don’t already know or realise, perhaps!

336) What scrambles your brain every time you think about it?

337) Would you find it difficult to watch yourself back, if you was shown footage of the last week / month / year of your life, so far? Why / why not?

338) What is something you probably should do, but will never do?

339) What great idea would you like to try if you had enough money?

340) If you were given immortality, but there was one condition, what would stop you from accepting immortality?

Deep Questions To Ask Your Boyfriend

341) If a genie granted you 3 wishes right now, what would you wish for?

342) In what ways do you think you can be selfish? And in what ways are you selfless?

343) How do you think you get the right balance when it comes to putting yourself first, and being selfish?

344) What do you think about when you’re by yourself?

345) What do you think people automatically assume about you when they look at you?

346) What are three things do you value most about a person?

347) Who would you say are the five people that you’re closest to?

348) Who would you say are the five people that you spend the most time with? And would you say they are a positive influence, negative influence or neutral?

349) In what ways are you different when you’re around different groups of people? And why?

350) When do you feel most like yourself?

351) Do you think that there’s anything missing, or lacking in your life?

352) How have your priorities changed over the last few years?

353) Do you feel like you’re living your life to the fullest? In what ways are you and aren’t you?

Onto The Last Ones…

354) What’s been the biggest life change you’ve been through so far? (Good or bad!)

355) Do you have any phobias?

356) Do you have any irrational fears?

357) What was the best birthday you’ve ever had? And how was it spent?

358) How does it make you feel when the attention is on you?

359) Do you like or dislike surprises? And what’s been the biggest surprise in your life so far? (Whether that was planned by others, or not!)

360) What things make you feel the most uncomfortable?

361) How often do you push yourself out of your comfort zone and why?

362) What’s the first thing you think of, when you hear the word “home”?

363) What makes YOU feel safe and protected? Or “taken care of” and content?

364) What makes your heart feel all warm and fuzzy? (And is that actually a thing? – You tell me!)

365) If there was ONE question I had to answer completely and utterly honestly – what would you ask? (Because remember – this is a two way thing! If you’re looking for deep questions to ask your boyfriend to get him to open up, make sure you’re doing the same thing too and encouraging your boyfriend to ask you more questions as well!)

So there we have it!

We’ve stormed to the end of our mighty 365 deep questions to ask your boyfriend.

Woah! What a list. Don’t forget to save this, revisit, or even print it – getting into the habit of asking a different question every day, to strengthen your bond and bring you closer.

Hope you’ve found this valuable. All the best!

Love,
Ell_xx

Deep Questions To Ask Your Boyfriend