100 Flirty Questions To Ask Your Boyfriend To Spice Things Up

When you’ve been in a relationship with your boyfriend for more than a year, things that were once hot and freaky may have started dwindling down. Things are not as spiced up and intimate as they used to be. You still love him, though. But you’re no longer in your “honeymoon” period, where you have flirty fun, and things in the bedroom might seem a little monotonous. You want that deep, intimate love you once had with him.

This is normal, as it happens to most couples. The key is to find ways to spice things up to make love last longer. I have written a few articles in some ways, such as The Best Sexy Lap Dance Music Playlist To Turn Your Man On and 13 New Dirty-Freaky Sex Things Couples Need To Try. As you can see, it is never too late to rekindle the fire in a relationship.

Another way to get things hot again is asking flirtatious, deep intimate questions--questions that you probably have never asked your loved one. I have a list of 100 flirty and cute (and some freaky) questions to ask your boyfriend to spice things up in the bedroom. A favorite is to ask these questions via text and let him think about you romantically in bed but not be able to have you. By the next time you see him, he’ll be wasting no time to act out his answers.

The timeless flirty question games always include “This or That” or “Would You Rather” questions. They are cute and easy to answer, and although they may not be deep questions, you’ll still learn a lot, because they still leave room for explanation and story sharing. Or for some added fun try to answer these types of questions with “it depends,” that answer still merits a longer explanation.

Flirty “This or That” or “Would You Rather” questions make your loved one consider his options deeply. You’ll hope he answers “both” for a lot of them!
 

This question is an interesting one. Not many people would want either (sex, after all, is something between you and someone else which is intimate), but giving him an ultimatum to choose from would spike up some interesting conversation.

Most men see both of these as chores in the bedroom. It would be curious to see which one your boyfriend would prefer over the other. Maybe he even likes both!
 

“Have You Ever” questions get the ball rolling. These primarily rely on past experience, so not much deep thinking should have to go into the answers. That means there’s more time for cute storytelling and getting to know each other on an intimate level you probably have never dreamt of knowing each other.

Your boyfriend will like the fact you are curious about his experience in the bedroom, but he also would want to know more about yours. Then you both would want to launch into creating new romantic experiences for yourselves.

17. Have you ever watched pornography while in bed with a girl?
16. Have you ever mixed food and sex?
 

Although this gets sticky and messy, it would be good to see what his experience level is in this freaky department. It would also be good to see if he would be interested in doing it again, or at all.
 

This may get a little messy, regarding feelings. However, if you choose to ask this, consider the possibility he tells you the truth and tells you he has thought of someone else. This may hurt, but you can keep an open mind about it. After all, he is honest with you, which is a sign of true love. If the answer is “yes,” ask follow up questions. Who? Why? What is it about that person you admire? How can I be more like her and meet all your fantasies?
 

Different from the “Have You Ever” questions, “Would You Ever” questions do not dwell on the past but the future of you and your boyfriend. These will make him think, which will start to get his mind working on the fact of sexy, cute and romantic things for you and him to possibly try. Even if the answer is “no” to some of them, it will open up both of your minds to the possibilities.

“Would You Ever” questions also strike up a deep conversation about why he wouldn’t do certain things, or to make a plan to play out a “yes.”

26. Would you ever change anything in the bedroom if you could? 
27. Would you ever go to a sex store?
 

If the answer is “yes,” then get over to one! Make it a big adventure and go together. Buy things for each other and things you both can use and try together.
28. Would you ever use edible underwear?
29. Would you ever do it at work?
30. Would you ever get your member pierced?
 

The answer will most likely be “no,” but you’d be surprised!

The most powerful sexual stimulant is the imagination. Ask your man the following flirty “If” questions to spark up the right-side of the brain—the creative and imaginative side. The great things about these questions are that they do no merit an easy “yes” or “no” response. Your boyfriend has to think of responses and come up with something to answer.

See what your boyfriend is capable of dreaming up with these “If” questions!

32. If you could have a threesome with me and any celebrity (boy or girl), who would it be? 

Hopefully, you both have this celebrity crush in common.

33. If we could have sex in any location, what would it be? 
34. If we were to do it in public, where would you want to do it?
35. If we could play a strip version of any game, what would you choose?
36. If you had to name your member, what would you name it?
37. If you had to name my lovely lady part, what would you name it?
38. If you had to name my twins, what would you name them?
39. If we met at a bar and you didn’t know me, what would your opening pick up line be?
 

Not many people meet each other romantically in a public place like the old days. With the dawn of modern technology, it is common for people to meet through a dating app. So if you didn’t meet your boyfriend in some romantic way, like shopping for produce in the local supermarket, don’t worry. But I’m sure you would be curious to find out what pickup line your boyfriend would use that would grab your attention?

The more cheesy the answer, the better!

These are a fun and flirty play on the basic “What” root questions. Again, these cannot be answered in just a “yes” or “no” manner. To answer these questions, your boyfriend will need to think. Add flirtatious tones to these question roots and your boyfriend will have nothing on his mind besides you and him and the bed (or wherever his dirty mind will place you two).

43. What is one thing you have always wanted to do with me but never asked?
44. What is your favorite part of me? 
45. What is one thing I do that drives you crazy (in the good way!)?
46. What time of day do you find yourself craving me? 

47. What was your first time like? 
48. What is the kinkiest and the freakiest thing you've ever done? 
49. What do I taste like?
50. Is it different each time?
51. What would be your ultimate song to have sex every time to?
52. What is your favorite position?
53. What is one thing you like about yourself?
54. What is one role play fantasy?
 

Note that this does not ask IF he has a role play fantasy. He can’t get away with a simple “no” for this. Make sure you pay attention to how you phrase questions now because asking him WHAT role play fantasy he does have, he will be more inclined to admit the one secret desire of his he hasn’t told anyone. But be prepared to help him make this fantasy a reality!

55. What is your favorite outfit of mine?
56. What is your greatest accomplishment in the bedroom?
57. What do I do better than other girls you’ve been with?
58. What would be one dare you’d have me do in a game of truth or dare?
59. What strip games have you played in the past?
60. What would you do if I sent a sexy and dirty pic of myself
61. What would you want a sexy or dirty picture to be of?
62. What’s your ideal date?
63. What do you think of me when we spend a night apart? 
64. What’s your favorite place to be kissed?

Talk about a flirty question! This question begs for an answer that receives an instant gratification response.

65. What is the hottest tattoo you’ve ever seen?
66. What is the most romantic gesture you have ever made?
67. What is the hottest thing a girl could say to you?
68. What would be your ultimate vacation destination? 70. What would be the ideal food to bring into the bedroom?
71. What do you think is my favorite thing about you?
72. What do you think I find sexiest about you?
73. What do you sleep in?
74. What is the cheesiest pick up line you’ve heard?
75. What pet name would you give me?
76. What is one thing in your bedroom you don’t want anyone seeing?

This one is fun and flirty! Especially if you are not living with him, or in his room all the time, you might wonder, “what goes on in there?” Ask him this and his secrets will come out. And when secrets come out, there is a whole other level of trust in the relationship that makes him want to trust you with more, especially if it’s dirty.

Sure, these don’t fit into the other categories. That’s what makes them miscellaneous. But don’t count these questions out! They are just as flirtatious as the previous ones. There’s a mix of flirty questions in here, but they all have the same end goal in mind: spice things up with your boyfriend.

These questions will stimulate the idea of you and your man alone and ready for things to heat up.
77. Would you want me to make more noise or less noise?
78. Is lingerie worth wearing for the short amount of time it’s on?
 

A lot of women think that if they wear lingerie, guys will want them more. But some guys don’t even care what the girl is wearing, especially when it is only on for a short amount of time before you get freaky and the clothes come off. This question also poses a thought in your man’s mind of you wearing either a sexy piece of lingerie or nothing at all. It’s a win-win.
 

Remember that kid’s game where you were given a set of different-looking people, and you had to ask questions based on what you think your partner’s person looked like? Imagine what features your boyfriend would use to distinguish you from other people.

My boyfriend and I don’t particularly need to spice things up. He keeps things interesting already as it is. His sarcastic, comical attitude about life constantly and makes every day a different story with us. So, I decided to get his input on this subject matter, since he’s an expert and all. He’s not a romantic guy, and he hardly would ever be considered flirtatious. Even if I am trying to be flirty with him, he doesn’t exactly get the hint.

For fun, I asked my boyfriend what flirty questions would spice things up between us if things ever got dull. Naturally, he gave me the following (he's lucky he's cute!):

He was such a help on this project, and those four questions would make your boyfriend happy! However, I would stick with the first 96 flirty questions suggested.

Relationships are always bound to come to a dulling moment. To keep things alive, intimate, and wild between you and your boyfriend, ask him flirtatious questions. You can use cute, innocent ones, or daring, freaky questions--either way they're fun for both you and your boyfriend. They get his mind working, they spark conversation, and they stimulate both of you, so you are ready for a night of fun. Even after a few questions, your boyfriend will be itching to get you in bed. Imagine what 100 questions would do. What are you waiting for?