90+ Flirty, Intimate & Personal Questions for Your Boyfriend

The best couples' questions to ask your BF in person or over text

Co-authored by Lauren Sanders and Glenn Carreau

Last Updated: July 26, 2023

You’ve got an amazing boyfriend, and things are going great, but there’s so much more you want to know about him! Asking fun and juicy personal questions is certainly a great way to get to know him better, which is why we’ve outlined all the juiciest topics to cover with your boyfriend. Read on for a long and detailed list full of example questions to get you started, from playful questions about his interests to flirty (and downright naughty) questions that’ll add a little spice to your relationship.

1

“When did you laugh the hardest?”

Download Article

Playful questions are the perfect start to a lighthearted conversation. Ever wish you had more super entertaining conversation starters in your back pocket, or feel like there’s a lull in the conversation but aren’t sure how to change it? It’s normal to feel like that sometimes, but don't worry; just engage your boyfriend by asking a fun, witty question.^{[1]
X
Research source}
- “Are you a morning person or a night person?”
- “What was your first concert?”
- “Do you believe in aliens or UFOs?”
- “Did you ever sleep with stuffed animals?”
- “If you won the lottery, where would you travel and why?”
- “Who would play you in a movie about your life?”
- “Are there any unsolved mysteries that interest you?”
- “If you could pick a theme song for yourself, what would it be?”

2

“What musician is your guilty pleasure?”

Download Article

Get the scoop on all of your boyfriend’s interests and favorite things. It’ll help you get to know him better—and, as a bonus, showing interest in his personal preferences is a great way to show him that you really care. Come up with creative questions about his favorite hobbies, songs, films, places to visit, and more!
- “What’s your comfort movie?”
- “What's your go-to karaoke song?”
- “What’s your favorite take-out food?”
- “What's your favorite holiday^{[2]
  X
  Expert Source
  
  Lauren Sanders
  Matchmaker & Dating Coach
  
  Expert Interview} (and holiday food)?”
- “What’s your favorite board game?”
- “What hobby do you feel you’re best at?”
- “Who’s your celebrity crush?”

3

“What’s your favorite love song?”

Download Article

Sweet and thoughtful questions are sure to get your boyfriend’s attention. Want to give your boyfriend butterflies without getting too raunchy? Then ask him a few cute questions the next time you’re out together. Gentle (yet definitely romantic) questions can be a great stepping stone for bolder ones in the future—or they can simply set the tone for a sweet and intimate conversation!
- “What's a hobby you think we should try together?”
- “Do you prefer fancy or casual date nights?”
- “What's your favorite memory of us?”
- “What was the last dream you remember having?”
- “Do you believe in soulmates?”
- “Have you ever kissed someone under mistletoe?”
- “If you could have three wishes from me, what would they be?”
- “What's something you're passionate about that you never get to discuss?”

4

“What’s your best pickup line?”

Download Article

Flirty questions can help maintain the spark between the two of you. You can flirt at any stage of the relationship—it doesn’t matter if you’ve been together for 5 weeks or 5 years! Flirting can preserve the attraction (or reignite the spark) between you and your boyfriend because it’s one of the easiest ways to communicate interest. It lets your boyfriend know you’re super into him!^{[3]
X
Research source}
- “Do you remember what I wore on our first date?”
- “What gives you butterflies?”
- “How often do you think about me?”
- “What was our first kiss like for you?”
- “What types of compliments do you like to hear?”
- “How do you think I should describe you to other people?”
- “Have you ever been skinny-dipping?”

5

“What’s your dirtiest fantasy?”

Download Article

Turn up the heat with spicy questions for your boyfriend. When you want things to get a little more heated between you and your boyfriend, how can you up the ante from playful and romantic to downright seductive? Ask him steamy questions—they can definitely set the mood and create some serious sexual tension!^{[4]
X
Research source}
- “What’s the kinkiest thing you’ve ever done?”
- “Do you ever fantasize about me?”
- “What positions have you always wanted to try with me?”
- “Can you guess what color underwear I’m wearing?”
- “Have you ever taken a bubble bath with someone?”
- “If you could touch me in one place, where would it be?”
- “What kind of foreplay do you like?”
- “What time of day are you most aroused?”

6

“What was the first thing you noticed about me?”

Download Article

Questions about attraction may reveal more about his preferences. Ever wonder what your boyfriend likes most about you? Or what things turn him on? It’s easy enough to find out by asking him about the things that attract him—particularly things about you.
- “What's your favorite physical feature of mine?”
- “What is your biggest turn-on?”
- “What qualities make me special to you?”
- “What color should I wear more?”
- “How do you describe me to other people?”
- “What type of scent do you like on a person?”
- “What’s something you think is true about me, but you've never asked to confirm?”
- “What do I do that makes you laugh?”

7

“Have you ever been in love before?”

Download Article

Juicy questions about your guy’s past can help you get to know him. Curious about your boyfriend’s life before you met him? His childhood, family, or even past relationships? In order to move forward together, it’s important to understand one another’s pasts. Don't be afraid to answer questions about your own past, too!
- “What were you thinking on our first date?”
- “When you were a kid, what career did you want to have?”
- “How many past partners have you had?”
- “What was your childhood like?”
- “Have you ever been cheated on by a partner before?”
- “What were you looking for when you found me?”
- “What's the hardest decision you've ever had to make?”
- “Did you debate whether or not to ask me out?”

8

“Do you remember your dreams?”

Download Article

Surprise him with a random, quirky question he’s never heard before. Does it feel like you know absolutely everything there is to know about your boyfriend? Odds are, there’s something new and juicy to discover about him (and for him to discover about you)—the trick is thinking outside the box! Ask him a few unconventional questions that might seem a little out there but can reveal a lot about him.
- “If you started a podcast, what topic would it be about?”
- “What's a hidden talent you have that you never get to show off?”
- “Do you ever feel like you lived a past life?”
- “What's one fact no one else knows about you?”
- “What do you think your best attribute as a boyfriend is?”
- “Do you sing in the shower?”
- “What's the craziest dare you've ever accepted during Truth or Dare?”

9

“What makes you feel fulfilled?”

Download Article

Deeper questions can help you build emotional intimacy. It might take you a little while to work up to the more serious, probing questions—but they’re the key to helping you connect with your boyfriend on a deeper level. Just remember that reciprocity is important; ask him deep questions, and be prepared to answer them yourself!
- “What's the biggest misconception people have about you?”
- “What's your biggest fear? Do you think you could face it?”
- “How would you define success?”
- “Are you proud of your accomplishments thus far?”
- “What gets you out of bed in the morning?”
- “What's the biggest risk you've ever taken?”
- “Do you believe in second chances?”
- “What scares or worries you the most about relationships?”

10

“What’s your love language?”

Download Article

Strengthen the relationship by learning how he expresses his love. In any healthy relationship, your ability to give and show love is what makes it last. So, it’s important to know how your boyfriend shows love and how he wants you to do the same! Ask romantic questions about love and committed relationships so he knows you truly value what you have together.
- “How do you like to show love?”
- “How do you want me to show love to you?”
- “What can each of us do to improve our relationship?”
- “Do I make you feel valued?”
- “When did you know you were in love with me?”
- “Do I make you feel heard?”
- “What's your favorite thing about our relationship?”
- It may be very helpful for both of you to find your love languages and discuss them together, since the concept of “love languages” defines different ways to give and show love.

11

“What’s your definition of intimacy?”

Download Article

Questions about intimacy can help you understand each other’s desires. Communication is super important in any relationship! Talking about what intimacy means to each of you can help you and your boyfriend develop a satisfying sex life and build on the intimacy you share in day-to-day life and activities.^{[5]
X
Research source}
- “Are you satisfied in the bedroom?”
- “Do you think we spend enough time together?”
- “Do you think we have healthy emotional intimacy?”
- “Is there anything we haven't tried that you'd like to?”
- “Do you wish I was more affectionate?”
- “Is our relationship physical enough for you?”
- “How many times do you think couples should have sex a week?”
- “What's your favorite type of kiss?”

12

“Where do you see our relationship heading?”

Download Article

Serious questions about the future can determine long-term compatibility. The future can be scary, but the best way to face it is head-on, arm-in-arm with your partner. Ask your boyfriend questions about the future and find out where the relationship is going—because it’s important for you both to be on the same page going forward.
- “What are your job or career goals?”
- “What kind of memories would you like to make with me?”
- “Where do you see this relationship in the next 5 years?”
- “What goals do you have for us?”
- “What’s your opinion on marriage and children?”
- “How do you imagine a day in the life of us married with kids?”
- “Do you ever worry about us breaking up? How can I help you feel better?”

Expert Q&A

Search

Add New Question

Question

What are some other fun questions can I ask my boyfriend?

Lauren Sanders
Matchmaker & Dating Coach
Lauren Sanders is a Professional Matchmaker, Dating Coach, and the Founder of Dating for the Soul. With over four years of experience, she specializes in helping singles find love. Lauren is also the author of Lipstick Faith: A Collection of Inspirational Writings and Life Lessons, You Deserve the World, Rainbows and Strawberries: 100 Devotions for the Brighter Side of Life, and Let's Go Outside Mommy. Lauren holds BS from Dillard University and a Masters from The University of North Georgia.

Lauren Sanders

Matchmaker & Dating Coach

Expert Answer

You could ask him about the first time he fell in love (and why things didn't work out with that partner), as well as when his last break-up was (and why it occurred). You could also ask about his favorite subject to learn in school, his favorite place to travel to, and a culture or ethnicity he'd most like to belong to (and why he would choose it).

Thanks! We're glad this was helpful.
Thank you for your feedback.
If wikiHow has helped you, please consider a small contribution to support us in helping more readers like you. We’re committed to providing the world with free how-to resources, and even $1 helps us in our mission. Support wikiHow
Yes No

Not Helpful 1 Helpful 1