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218 Personal Questions to Ask A Guy

Are you interested in someone but finding it hard to get close to them? Maybe you’re at the beginning of a relationship and looking to get to know more about your new man? Sometimes it might seem difficult getting to know someone, especially if the person you are trying to get to know isn’t very open. However, there are so many questions that you can ask a man to get him to open up to you a little bit more and open the door to getting to know each other on a deeper and more intimate level.

I have put together this article to provide you with an array of questions that are good to ask your man which should allow him to open up to you. There are two hundred questions that you can ask a guy, or your partner, in particular, featured in this article. With a large variety of questions, hopefully, you can choose whichever ones suit you and your man best.

It completely depends on how confident and comfortable you feel around this man as to how you’re going to ask these questions. If you feel like it’s better to ask him some of these questions, then that might be a good idea. This is also really useful for him, if he isn’t very confident talking in person – it might allow him to open up a bit more than he normally would face to face.

If you feel like you’re ready to ask him some of these questions in person, you should try to ask them in an intimate and comfortable environment. Don’t just spring any of these questions on him. A good example of a time you might want to ask some of these questions is when you’re cuddling in bed. He will feel safe and able to express himself fully to you without anyone else overhearing.

So, let’s go ahead and take a look at the personal questions you can ask a guy to get to know them on a deeper and more intimate level.

Personality questions.

We are going to start with some questions that will open up a little bit more of his personality to you. If you don’t know the guy too well or you aren’t quite comfortable enough yet to send flirty messages, these can provide really good starter questions.

1.   What makes you your happiest?

2.   What makes you feel sad?

3.   Do you believe in religion? Or what do you believe in? Do you follow any faith in particular?

4.   What are your goals in life?

5.   What are some of the rules that you choose to live by?

6.   What do you really want to do? Or are you already doing it?

7.   Where did you grow up?

8.   Do you have a good or bad relationship with your parents?

9.   Do you have siblings? Do you get along with them?

10.   Who are your best friends?

11.   What’s your idea of the best day ever?

12.   What are your political views?

13.   Who’s your favorite person in the world?

14.   How would you describe yourself?

15.   What kind of music do you like?

16.   Do you like going to the cinema or theatre?

17.   Do you play any sports? Do you like sports?

18.   What do you love most about yourself?

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19.   What do you wish you could be better at?

20.   What’s your idea of a really amazing date?

21.   What’s your type?

22.   Are you a stay at home or go out and party kind of person?

23.   What has been the best day of your life so far?

24.   Do you have a bucket list? What is on it?

25.   Do you have any really embarrassing stories?

26.   What’s your favorite food? What would your death-row meal be?

27.   Where is your favorite restaurant?

28.   What’s the best place you have ever traveled to?

29.   What’s your favorite book?

30.   What’s your favorite film?

31.   What’s your favorite song?

32.   Are you scared of anything?

33.   Have you ever done extreme sports?

34.   Have you ever made any enemies?

35.   Have you ever been a bully?

36.   What’s your biggest regret?

37.   What do you look for in a partner?

38.   Do you have any tattoos? If so, what do you have and where is it?

39.   If you won or inherited a lot of money, what would you do?

40.   What’s your ideal home?

41.   What’s your favorite thing to cook? Or, what is your signature dish?

42.   What’s the craziest thing you have ever done?

43.   Do you wish you had done things differently in the past? 

44.   Do you believe in the after-life?

45.   Do you believe in ghosts?

46.   What’s your all-time favorite car and why?

47.   If could, would you change anything about yourself?

48.   Can you ride a motorbike? Do you want to get one?

49.   When you were a child, what did you really want to do for a job when you were older?

50.   What was your biggest childhood dream?

51.   What’s your favorite thing about me?

52.   If you never had to work again, would you?

53.   If you never had to worry about money, what would you do?

54.   What is the craziest fact about yourself?

55.   Do you have any hidden skills?

56.   What’s something you have never told anyone before?

57.   What’s your dream destination?

58.   Do you like animals?

59.   Would you ever get a dog or a cat?

60.   Do you want kids in the future?

61.   What are your views on climate change?

62.   What’s the coolest band you have ever seen live?

63.   Have you ever met anyone famous?

64.   Would you like to be famous?

65.   Do you prefer the countryside or the city?

66.   Do you like the beach?

67.   Have you ever been skiing or done winter sports?

68.   What do you want your life to be like in the new few years?

69.   Have you ever got into trouble with the police?

70.   Have you ever done anything illegal?

71.   What do you think people think of you?

72.   Do you believe in ghosts? Have you ever seen a ghost?

73.   What’s your favorite thing to do in your free time?

74.   What’s your best party trick? Show it to me.

75.   If you could have a superpower for one day, what would it be?

76.   Do you have any bad habits?

77.   Do you have any regrets?

78.   Are you creative or academic?

79.   What did you study?

80.   What are your strengths and weaknesses?

Sexual questions.

Hopefully, after using some of those personality questions you will have a better idea of who this guy you’re speaking to and how his mind works. Those questions should have helped you to both bond on a deeper level, but it’s now time to think about the nature of your relationship. If you want to have a romantic or sexual relationship with this man, you are going to need to start talking to him in a more romantic and sexual way. These next set of questions are here to get the spark between the two of you lit and hopefully, it won’t be long before you start being more than friends. A lot of these questions will probably lead to the two of you sexting or just getting together as soon as possible for some hot and heavy action.

The important thing is, It’s completely up to you which questions you ask him, of course, but you need to make sure that you are comfortable with everything you are saying to him. These questions vary in their sexual nature, and some of them are naughtier than others, so just make sure you’re happy and confident in what you’re saying. Don’t feel like you have to ask the naughtiest questions if you don’t want to.

81.   What turns you on?

82.   What is a definite turn off for you?

83.   Do you have any fantasies?

84.   Do you have any fetishes? What are they?

85.   How often do you masturbate?

86.   Have you ever had sex outdoors?

87.   What’s the craziest place you have ever had sex?

88.   What’s the craziest place you have ever masturbated?

89.   Do you like receiving nudes?

90.   Would you ever send nudes?

91.   How many times a week is your ideal number to have sex?

92.   Are you the kind of guy that likes to be in control or likes to be controlled in the bedroom?

93.   Have you ever slept with someone on the first date?

94.   How many people have you slept with in total?

95.   What do you think is the hottest thing a woman can do?

96.   What do you sleep in?

97.   Have you ever had a threesome? What do you think about them?

98.   What kind of porn do you watch? Would you like it if we watched it together?

99.   How good is your stamina in the bedroom?

100.           What’s the best sex you have ever had and why was it so good?

101.           What’s the worst sexual experience you have ever had and why was it so bad?

102.           Do you prefer shaved or not on a woman?

103.           Have you ever experimented with someone of the same sex?

104.           What would be your dream sex situation?

105.           What’s your favorite – ass or tits?

106.           What would you love to see me wearing?

107.           Do you like it when a woman tells you she fingers herself?

108.           Have you ever done anal with anyone?

109.           What’s your favorite outfit for a woman to be wearing? Would you like to see me wearing that?

110.           Is there anywhere on your body in particular that you love being touched or played with?

111.           Have you ever had shower sex?

112.           Do you like sexting?

113.           Have you ever been to a strip club?

114.           Would you like a girl to do a striptease for you?

115.           Have you ever had phone sex?

116.           When did you lose your virginity?

117.           Do you moan when you have sex?

118.           What are your views on sex toys in the bedroom?

119.           Would it freak you out if I said I use sex toys?

120.           Are you into rough sex?

121.           How often do you like to have sex and when was your last time?

122.           How many one-night stands have you ever had?

123.           What time do you like to have sex? In the morning or at night time?

124.           What do you think about when you masturbate? Have you ever thought of me?

125.           Would you ever send a nude to me? If I sent you one in return?

126.           What do you think I taste like?

127.           Have you ever been tied up whilst having sex?

128.           Would you have sex in a public place?

129.           Have you ever had sex in a car?

130.           What’s your favorite thing to do during foreplay?

131.           Do you ever think about me naked?

132.           Do you like it when someone talks dirty to you?

133.           Have you ever been caught having sex or masturbating?

134.           Do you like blowjobs or handjobs?

135.           Have you ever recorded a sex video? Would you record one in the future do you think?

136.           Have you ever given someone a massage that’s turned into sex?

137.           What’s your favorite type of lingerie for a woman to wear? Do you like suspenders?

138.           Have you ever or would you ever try BDSM?

139.           Have you ever had sex with more than one person on the same day?

140.           Would you like being sucked off while you drove?

141.           How would you describe your style of having sex? Are you rough or gentle and loving?

142.           Would you have sex on a plane?

143.           Have you ever had sex underwater?

144.           Do you ever picture what people look like naked? Have you ever done that with me?

145.           Do you speak to your friends about your sexual encounters?

146.           Have you ever given a hickey or received one?

147.           Do you like having sex in the dark, or with the lights on?

148.           How would you feel about having sex in front of a mirror or with a mirrored ceiling?

149.           Do you like going down on women?

150.           Do you think you’re selfish in bed or do you prefer to give the other person a lot of pleasure?

151.           How long would sex last with you?

152.           What’s your favorite sex position?

153.           Do you want to have sex with me?

154.           Do you think we would have good sex?

155.           Would you like it if you had a personal sex slave for the night?

156.           What makes you cum instantly?

157.           How often do you think about sex?

158.           Do you think I could make you cum fast?

159.           Have you ever been to a brothel or used a prostitute?

160.           Have you ever had someone watch you have sex?

Romantic questions.

Of course, sexual questions are a great way to get your partner and you feeling closer, and it will probably lead to sexting each other or dirty talking. You will get to know what each other’s likes and dislikes are. However, if you are looking for a romantic relationship as well as a sexual relationship with this person, you might want to ask them some personal questions about the future and the relationship that you share together.

It’s quite important that you pick and choose when to ask these questions at the right time. The questions are going to include some serious and big topics like marriage and having children. Therefore, these are the kind of questions that you should not ask on the first date. It might be a good idea to try and bring these questions slowly into a conversation to test the water. You shouldn’t outright ask a guy these kinds of questions if you’re not already on a similar topic, otherwise they will most likely freak out and run in the other direction. So essentially, you need to have a pretty good relationship with this guy before you start asking him these kinds of things. If you are at that stage, and you are pretty open about each other and discussing the future then these questions are perfect ways to see if you have similar visions about the future and views on romance in general.

161.           What do you think about love?

162.           Do you think that we all have soul mates?

163.           When was the first time you fell in love?

164.         Do you believe in marriage?

165.         Do you want to get married one day?

166.         Do you think marriage is necessary before children?

167.         What would be your dream marriage?

168.         How long do you think you should be in a relationship before you get engaged and married?

169.         Do you want children at some point in the future?

170.         What do you visualize for yourself in the future? Do you want to live in a particular kind of house or have a big family?

171.         Do you think love is the same as lust?

172.         Do you like to cuddle?

173.         Is the physical part of a relationship important to you?

174.         Have you ever kissed someone in the rain before?

175.         Do you like public displays of affection?

176.         What do you think is the most important thing in a relationship?

177.         How would you describe the relationship between us?

178.         Have you ever dreamt about me?

179.         Do you see a future between us? If you do, what is it like?

180.         Have you ever written a love song or a love letter? Would you?

181.         Do you believe that love is the most important thing in the world?

182.         What do you want to call your children?

183.         Do you think you would be a good father?

184.         Would you ever cheat on someone?

185.         Have you ever been cheated on before?

186.         Do you have any relationship deal breakers?

187.         What are you looking for in a partner?

188.         Is love about looks or personality to you?

189.         Do you ever miss me when I am not around?

190.         What do you think is the most romantic thing ever?

191.         Do you think having sex turns into making love when you are in love with someone?

192.         Do you want to be the best version of yourself when I am around you?

193.         Would you be happy to wear sweats and watch films with me all night rather than go out to a fancy dinner?

194.         What’s the best way to resolve a fight?

195.         Do you think you should get in relationships where your partner is like your best friend?

196.         Do you want to grow old with me?

197.         Have you ever thought about marrying anyone else before?

198.         What makes you fall in love?

199.         How does it feel to be falling in love with me?

200.         What are you looking for in this relationship?

Funny and flirty questions.

After speaking about some very serious questions, sometimes it’s also a  good idea to keep the chat light with a man. As we all know, men are less open than women in the first place but they also lose concentration a lot faster too. So, if you try to speak to him for hours about why he loves you or what he is looking for in the future, you will probably lose him. Also, if it becomes a pattern that every time he speaks to you an intense conversation or serious questions come up, he might run for the hills. Your relationship, of course, should be serious but to a certain extent. Relationships are supposed to be happy, and you are supposed to have fun with each other. You don’t want him to think that every conversation you have with him is going to be really deep. So, you need to mix it up and ask him some fun and flirty questions from time to time too.

Having someone make us laugh is actually one of the most attractive qualities in a person. So, if you make him laugh, he is going to want to be around you more and more and will become more attracted to you. That’s the goal, isn’t it? So let’s get him having a giggle. Sharing the fun times as well as the serious ones is also a key way to bond on a deeper level because it creates memories and personal jokes too.

201.           Have you ever been caught in your birthday suit?

202.           What’s the best joke you have ever said?

203.           What’s the most embarrassing story to ever happen to you?

204.           What is the worst outfit you have ever worn and where is the photographic evidence?

205.           What’s the weirdest thing you have ever seen someone do when you were stuck in a traffic jam?

206.           Were you ever called any funny names as a kid?

207.           What’s the funniest and worst name you could ever think of giving a child?

208.           What’s the funniest thing you have ever done when you’ve been drunk?

209.           What would a woman look like if she was a copy of you?

210.           If you were arrested, what would your friends think you had done?

211.           What is the funniest memory that we have together?

212.           Would you get excited if all of a sudden you woke up in a woman’s body? What would you do first?

213.           If you were a porn star or a stripper, what would your name be?

214.           What’s the most ridiculous way that you have ever hurt yourself?

215.           What would be the funniest idea of a date for you?

216.           What geeky thing makes you laugh?

217.           Who would play you if your life was portrayed in a film? 

218.           When was the last time you danced around in the shower whilst singing your all-time favorite love ballad? Come on, I know you do it!


I really hope that this article has helped you with some ideas of what you can text a guy, or more specifically your guy, to get the two of you speaking a little bit more openly. In any new relationship, it always takes a bit of time to open up with each other. Men normally open up a lot slower than women do, so don’t worry if you are telling him more about you than he is about you. Hopefully, within no time you will be extremely close and able to take your relationship to the next level.

I wish you all the best of luck getting to know your man and finding out more personal things about him.

Did this article help you at all? If it did and you liked what you read, please let us know in the comments. We would love to hear from you.

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Whether you're married or just started dating someone, infidelity rates have risen by over 40% in the past 20 years, so your concerns are justified.

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This tool can help by uncovering hidden social media and dating profiles, photos, criminal records, and much more, potentially putting your doubts to rest.


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