What are the Best Questions to Ask a Man?

Planning a date with the new man in your life? Meeting with a guy through a dating app or on social media? Looking to connect with an old flame or impress a friend or co-worker with a view to dating them?

If so, you need to arm yourself with some questions. A good question can make a good first impression, get the conversation flowing, and set you up for future conversations.

Flirty Questions to Ask a Man

• What do you think is the most attractive thing about me? I’ll tell you yours if you tell me mine.
• What is your love language?
• Do you believe in love at first sight?
• Do you believe in soulmates?
• What is your favorite pick-up line?
• What is the worst pick-up line you have ever heard?
• What are the emojis that you use the most?
• If you could be represented by an emoji, what would it be?
• What do you look for in a partner?
• What is the one sentence that could win over your heart more than any other?
• What would your perfect first date look like?
• What is the last thing you think about before you go to sleep?
• Which actor do you think you are most alike in terms of attractiveness?

Personal Questions to Ask a Guy

It is time to get a little more serious. It’s all fair and well being funny, weird, flirty, and even embarrassing, but your goal is to know more about him. Whether you see him as a potential partner or simply a best friend, there will come a time when you need to ask more personal questions.

So, after you break the ice and feel that the time is right, slip some of these personal questions into the conversation.

Ask about his life experiences

• What has been the absolute favorite week of your life so far, and why?
• Have you ever remained friends with an ex-partner and regretted it?
• What is the longest relationship that you’ve ever had?
• Do you have any regrets about your studies or work?
• What is the last thing that ever made you cry?
• Have you ever arrived for a date, taken one look at them, and then wished you could walk away?
• What or who do you wish you had more time for in your life?

Ask about his preferences

• What are the three things that you love the most and could never give up?
• Who did you idolize when you were younger, and what was so great about them?
• What is your favorite movie of all time?
• What is your favorite food, and what food can you simply not eat?
• What is the biggest dealbreaker for you on a date?
• What trait would turn you off a partner quicker than any other?

Create fun scenarios

• If you met your teenage self today, would you like yourself?
• If you could learn any skill in an instant and start work on any career path tomorrow, which skill and profession would you choose?
• If you could go back in time and change 1 spoken sentence in your life, which one would have the biggest impact and completely change where you are today?
• What or who do you wish you had more time for in your life?

Fun and Funny Questions to Ask a Guy

Humor is always a good way to a man’s heart. You can also encourage him to tell a joke, such as by asking about the funniest thing or the craziest thing he has ever seen or heard. Don’t be afraid to be a little silly or weird. Mentioning an embarrassing thing is good as well, as it lowers his guard and shows him that he can reciprocate with a similar story.

Here are a few funny and fun questions to ask him:

• I once (INSERT EMBARRASSING STORY). What is the weirdest thing that has ever happened to you?
• There is a zombie apocalypse tomorrow. What is the very first thing that you do and are you able to survive for more than a year?
• If your life was made into a movie, who would play you, and who would play the other people in your life?
• Do you listen to any unpopular music that you love but haven’t told your friends about?
• What do you think would happen if you traveled back to medieval times?
• If you could have only 1 superpower, what would it be, and how would you use it?
• What TV show or movie do you love but are too scared to admit to anyone?
• If your life was turned into a TV show, what would the theme song sound like?
• What would you do if you woke up as a woman tomorrow?
• If someone gave you $1 million tomorrow, what would you do with the money?
• You find a genie in a lamp and he gives you three wishes. You can’t wish for more wishes and you can only wish for selfish things (no world peace!) What are your wishes?

Questions You Should Ask Over Text

Many of the questions on this page will work over text, social media, dating apps, and in person. There are some considerations, though. With text, you want to keep it short and encourage a good flow of conversation. You want to hold their interest and learn more about them while creating moments in the conversation where you can ask them on a date.

Some of the interesting questions to ask over text include:

• What game from childhood do you still love?
• Who do you think is the GOAT of all sports?
• When did you have your first kiss, and what was it like?
• Have you ever fallen in love before?
• How long was your first relationship?
• How long was your longest relationship?
• Have you ever had a one-night stand?
• What movie sequel or reboot do you want to see more than any other?
• If you had to try and make it as a pro gamer, which game would you choose?
• Who was your teenage crush?

Interesting and Thought-Provoking Questions

Let’s wrap things up by asking some thought-provoking questions meant to stimulate your mind. These questions typically elicit lengthy and comprehensive answers, making them ideal for face-to-face conversations.

Save these for when you have the chance to discuss them in person, as they are best suited for in-depth, real-time dialogue.

• If you could invite any 3 people from history to a dinner party, who would you choose?
• You walk into a dinner party and see 3 people at the table. It is the worst possible group of guests there could have been for you. Who are the three people?
• If you could be any animal, which one would you choose and why?
• If you could live anywhere in the world with no restrictions on budget or work, where would you live?
• If you could live at any time period in human history, what year would you choose?
• If you had a single day where you could do anything you wanted with no responsibilities and no budget, what would you do?

Conclusion: Fun and Funny Questions to Ask Your Boyfriend

Once the conversation is flowing, you don’t really need to think about questions. Everything will come naturally—that’s when you know you’re onto something good. But in the early stages and during lulls in the conversation, the questions above help to keep things going. They ensure that you don’t have any protracted silent spells, and they may also make him more comfortable and help him through those early nerves.

So, arm yourself with a few of these questions and try them out the next time you send a message to a man or meet him in person.

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