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100 Questions to Ask Your Boyfriend – 2021 Serious Questions

Questions are necessary if you really want to get to know someone. In a relationship, questions helps us understand each other better and avoid most misunderstanding. Questions helps us move from the initial stage of strangers to being friends and then being lovers. With question, you can know the background of your boyfriend, his past, his present and where he intend going in the future.  Much as questions helps build relationship, not all questions are same. In fact there are questions that have potentials to destroy a relationship. Knowing the right question to ask is therefore key in getting to know your boyfriend better.

While questions gives you an excellent opportunity to get to know your boyfriend, it also helps you to deepen your relationship with your boyfriend. There are also questions to ask if you aren’t sure of the direction of your relationship and want to know what he thinks about you and your relationship with him. We have put together 100 questions to ask your boyfriend. These questions range from deep questions, serious questions, questions to ask to turn him on, questions to ask before getting engaged or moving in with him and fun questions. Enjoy.

Serious Questions To Ask Your Boyfriend.

1. Do you still keep in touch with Your Ex and is an issue with you if I’m still in touch with my Ex?

The purpose of this question is to find out his relationship with his Ex. You don’t want to be in a relationship where your boyfriend is just using you to get over his ex. Also finding out his thoughts regarding being in touch with your ex gives you some insights on how your relationship with your ex should be should in case he doesn’t approve of it.

2. How long did your last relationship last and when did it end?

It’s important you know when he ended his last relationship and how long it lasted. This information is important as it gives you a clear picture of how committed or not he was in this last relationship. Also it tells you how soon he waited before moving into a new relationship.

3. How many sexual partner have you had?

While your intention is not to judge, you would not want to get into a relationship with a guy who has had several multiple partners. Knowing the number of partners he has had for his age gives you a clear information on his intentions in any given relationship.

4. When was the last time you tested for STDs/HIV and will you be willing to go for another test before things get more serious between us?
5. What’s your view on domestic violence and will there ever be a reason to hit a woman?
6. How do you start your typical day and how what do you do before you end each day?

7. Have you ever been arrested and for what offense?
8. What do you like to do to unwind and what’s your hobbies?
9. What habits have you developed over the years that have served you well and what habits have hindered you that you would like to change?
10. How do you handle conflicts or disagreement?

Serious questions to ask your boyfriend

Flirty Questions To Ask Your Boyfriend?

21. What’s your favorite panties color that you would love me to wear whenever I’m visiting you?
22. If you walk into my room and find me naked what would be your reaction?
23. How often do you get hard in a day and what do you do whenever you’re hard?
24. Have you ever masturbate and how often?
25. What are you most attracted to in my body?
26. A big ass or a big boo what’s your preference.. and don’t worry I won’t feel bad.
27. When did you have your first kiss and what was the experience like?
28. Do you like foul play before sex and is it something you would try with me?
29. Would you ever take a bath with me and would it lead to sex?
30. Do you like to cuddle? I love it.

Don’t Miss : Dirty Sexual Questions to Ask a Guy

31. You decide to give me a full body massage, where do you start?
32. If you can describe my body with three words, how would you describe it?
33. Would you rather see me in lingerie or nothing at all?
34. Do you like when I make the first move?
35. Do you like it when I’m on top?
36. If we were together for the whole day, how many times would you make love to me.
37. Do you like dirty talk?
38. Can you give me a good example of your dirty talk?
39. Can you talk me on via phone?
40. Have you ever tried phone sex.. would you like to try it with me?

flirty questions

Deep Questions To Ask Your Boyfriend

51. Do you have fears about our relationship?

We all have relationship fears. Sometimes it’s due to past hurts other times it’s due to the fear of the unknown. Asking and knowing what your boyfriend fears about your relationship with him gives you both the opportunity to address it together and make provision for it.
52. Do you believe in happily ever after?
53. What’s your ideal of a perfect relationship that leads to a wedding?
54. If you had one word to describe our love what would it be?
55. What did you think when you first met me?
56. What about our relationship makes you really happy?
57. What about love scares you?
58. If something happened where I had to move very far away, would you attempt long-distance? Or go our separate ways?

Some people believe in long distance relationship and put in their best to make it works, others don’t. Knowing what your boyfriend thinks about long distance relationship helps you know what the future holds especially if you’ll that in the near future it may become necessary to move to another city or live far apart.
59. What’s one thing you feel our relationship is lacking?

This an important question especially if you feel your boyfriend is not totally satisfied with your relationship with him. Asking and finding out what your relationship lacks gives both of you the opportunity to work at it and preserve your relationship.
60. If our relationship ended, what’s the one thing about it you’d miss the most?
61. When you break up with someone, how do you do it?
62. What are your thoughts on marriage?
63. Are you comfortable talking about where our relationship is going?
64. Do you see us getting married anytime soon?
65. If a girl asked for your number, would you give it to her?
66. Are you comfortable me still being friends with my ex?
67. If one of your friends or family members told you to break up with me because he/she didn’t like me, would you?
68. Have you ever had the thought that I’m not good enough for you?
69. Would you choose me over your friends if they need you same time I need you?
70. What makes me special in your eyes?

Deep Questions to ask

More Serious Questions To Ask Your Boyfriend

81. Do you have kids and how many?
82. Do you want kids and how many?
83. Is your present job your ideal job and how long do you intend working there?
84. When we get married, how would you like our bills to be paid?
85. Do you currently have any insurance and what’s your retirement plans like?
86. How will we make sure we each get to spend time alone when we share the same place?
87. How do you feel about taking in family members during a hard time? Elderly parents?
88. What are your thoughts on how to discipline children?
89. How will we spend our holidays?
90. How long did you think our relationship would last when we first started dating?

Fun Questions To Ask Your Boyfriend

91. Who was your celebrity crush as a teen?
92. How often do you pee in the shower?
93. What’s the grossest thing you’ve ever eaten?
94. Have you ever pretended to be a woman?
95. What’s the food you like to have the most on your birthday?
96. Have you ever dated someone from another race.. Would you?
97. Would you rather be smart and ugly or dumb and beautiful?
98. What turns you on and what turns you off?
99. What is your favorite food?
100. What is your favorite sport?

101. Do you watch Peacock Premium?