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100+ Interesting Questions To Ask A Guy To Spark Conversation & Connection

Author:

Kelly Gonsalves

September 26, 2023

Contributing Sex & Relationships Editor

By Kelly Gonsalves

Contributing Sex & Relationships Editor

Kelly Gonsalves is a sex educator, relationship coach, and journalist. She received her journalism degree from Northwestern University, and her writings on sex, relationships, identity, and wellness have appeared at The Cut, Vice, Teen Vogue, Cosmopolitan, and elsewhere.

Questions for the first date

Thought-provoking questions

Funny questions

Dirty questions

Questions to ask on a dating app

Questions to get to know them better

Tips to keep the convo going

September 26, 2023

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Sometimes you're texting a guy you like or you're out on a first date, and for some reason, your mind just goes blank. You have no idea what to say next or what questions to ask. It happens to the best of us!

If you need a little inspiration, here's how to be a sparkling conversationalist, both in person and over text, as well as a bunch of questions to ask a guy (or anyone) the next time you're stuck.

Questions to ask on the first date

Do you like your job?
How did you end up in your current line of work?
What personal goals are you working toward right now?
Do you enjoy dating?
What are you looking for from dating right now?
What do you look for in a partner?
For you, what does it mean to be in a relationship?
Why did your last relationship end?
What's your love language?
What are your relationship deal-breakers?
What's a topic or hobby you're randomly passionate about?
What's a social issue you're very passionate about?
Are you engaged with politics?
Are you religious?
How has the pandemic affected you personally?
Video dates: yes or no?
What do you prefer: texting or phone calls?
What's your approach to defining the relationship?

Thought-provoking questions to ask a guy

What does it mean when you say "I love you" to someone?
Do you believe in the concept of soul mates?
Is jealousy healthy in a relationship?
Is lying ever OK?
Is cheating ever OK?
Have you ever cheated on someone before? Why did you do it—and do you regret it?
Do you want to be more or less like your parents?
What do you wish you had more of in your life right now?
What do you wish you had less of in your life right now?
When was the last time you cried?
Do you talk about your feelings often? Why or why not?
Who do you feel most comfortable talking about your feelings with in your life? Who do you feel least comfortable doing that with?
What would you be doing if money wasn't a concern?
What are your thoughts on porn?
What do you want to be remembered for after you die?
What's more important: science or art?
What's your relationship to your gender?
What does masculinity or being a man mean to you?
What gender stereotype do you wish the world would let go of?
What does friendship mean to you?
What's the meaning of life?

Funny questions

Do you have any go-to flirting techniques or moves?
What's your favorite pickup line?
Who's your celeb crush?
Who was your celeb crush as a teenager?
Who was your first crush, and did you tell them?
Who would you want to play you in a movie?
If you had to give up one for the rest of your life, which would you pick: cheese or chocolate?
Cat person or dog person?
Would you survive a zombie apocalypse?
Would you survive being stranded on a deserted island?
What's your favorite conspiracy theory?
What reality TV show would you be on?
What's your most annoying habit?
What's the most embarrassing thing in your search history?
Is water wet?
What's the most useless talent you have?
Do you brush your teeth before or after breakfast?
The toilet isn't working at someone else's house. What do you do?
What's something trivial that you always lie about?

Dirty questions

Have you ever fantasized about me?
What's an unusual thing that turns you on?
How do you define good sex?
What's your dirtiest fantasy?
Wildest sex story?
Boobs or booty?
What do you find to be the sexiest part of a man/woman/person's body?
Do you like it when a girl makes the first move?
When did you first have sex? How did it go?
What's on your sexual bucket list?
Lights on or off?
Favorite sex position?
Fast and hard or slow and gentle?
Do you like anal?
What do you like better: oral or intercourse?
What’s the kinkiest thing you've ever done in bed?
Have you ever hooked up with someone of another gender?
What's the hottest memory you have of us?
What would you like to do to me tonight?

Questions to ask a guy on a dating app

What's the most interesting thing that happened to you this week?
What's a problem you're working through right now?
How are you feeling these days, really?
What sticks out to you in a dating profile?
What do you think about dating apps?
Any funny stories about people you've met from a dating app?
What's the worst date you've ever been on?
What's the best date you've ever been on?
What's your ideal first date?
Do you like your job?
What's something you're randomly extremely into?
What's your astrology sign, and do you think it's accurate?
What's the most interesting thing you've read recently?
What's your latest controversial hot take?
What's on your mind right now?
Do you want to meet up?

Questions to get to know someone better

What was your childhood like?
What's your relationship with your parents?
What were you like in high school?
What's your relationship to religion?
Are you a spiritual person?
How long does it take you to open up to someone?
What's your attachment style?
What parts of yourself are you working on right now?
Do you want kids? Why or why not?
How do you deal with conflict in relationships?
What was your last big fight about?
Do you have any big regrets in life?
Have you ever been in love?
Have you ever done anything illegal?
What do you want to do in retirement?
What's your favorite part of your typical day?
What does self-care look like for you?
What's a question you wish more people asked you?

Need some more inspo for questions to ask? Consider checking out the infamous 36 questions to fall in love or this couples' quiz.

How to ask questions that keep the conversation going

Whether you're on a date or just talking to the cute guy you always see in the elevator, the key to keeping a conversation going is to ask thoughtful follow-up questions. So, when someone tells you something—anything—listen intently, and then respond with a question that elicits a deeper explanation about what they just shared.

For example, if someone mentions they love the summer, ask what they love about it. If they tell you they're having a rough week, ask why that is.

If someone mentions they've been playing video games all day, ask what game they're playing and what's so fun about it. You can even go a level deeper: Do they consider themselves a serious gamer or a casual gamer? What's the first game they couldn't stop playing?

"Great interviewers know how to make people feel special by being genuinely fascinated by other people," couples' therapist Alicia Muñoz, LPC, recently told mbg. "Notice their response without jumping automatically back to yourself, your experience, your interpretations of what they said."

If you find the conversation comes to a lull, or you're just trying to strike up some interesting conversation, here are some ideas for questions to ask a guy or anyone you're interested in.