101 of The Best Questions to Ask Your Girlfriend

Dave Bowden

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Smiling couple hugging
Pretty much any guy who’s been in a relationship for any significant amount of time will tell you that knowing which questions to ask your girlfriend isn’t as easy as single guys (including our own formerly single selves) might have thought.

When you’re just flirting, dating and getting to know each other, figuring out the right questions to ask a girl is relatively easy. You know so little about her that every question reveals some new information, and you can have a lot of fun just making small talk and learning about the basics of each other’s biographies.

But as your relationship evolves, the questions you should ask your girlfriend need to evolve as well.

You need to shift the focus of your questions from “getting to know you” to “learning about each other on a deeper level,” all while keeping it as fun, flirty and engaging as possible.

The problem is that, after covering all the basic “getting to know you” questions, a lot of guys have trouble thinking of what questions to ask next, and they worry that asking their new gf the wrong question might even upset her, and ruin the good vibe they have going.

The good news is that evolving your questions and keeping the lines of communication with your girlfriend open is easier than you think.

All of the questions below are designed to engage your girlfriend in interesting and insightful conversations that will allow you to continue deepening your relationship, while steering clear of any topics or territory that might ruffle her feathers or risk upsetting the (sometimes rather delicate) balance of your relationship.

Wondering What Questions to Ask a Girlfriend?

Wonder No More! Here are 101 Engaging, Insightful & Fun Questions to Ask Your GF

29 Questions to Ask a New Girlfriend

Smiling attractive black couple
Asking questions on your first few dates is easy, because you know basically nothing about each other and can ask almost anything you want.

But as you get to know each other and begin the earliest phases of your relationship, you need to move past the small talk and start asking questions that will reveal a little more about her, while still keeping things as fun, flirty and engaging as possible.

The questions below are a little more personal than the standard small talk questions you ask when you’re getting to know each other.

Now that she’s officially become “your girlfriend,” you can use these questions to learn about aspects of her life that probably didn’t come up in the early dating stage of your relationship.

The Questions:

Who’s the first person you call when you need guidance or life advice?

What’s your biggest fear?

Are you more of a morning person or a night person?

Be honest: do you prefer giving or receiving gifts?

Are you a person who prefers structure and stability, or randomness and unpredictability?

Would you rather stand out from a crowd, or blend into it?

What’s one thing about you that no one else knows?

What’s your idea of the perfect Valentine’s Day?

What’s your worst dating story? Have you been on any particularly awful dates?

What’s your idea of pure comfort?

  • Leaving this open-ended allows her to interpret it however she likes. Maybe it’s an old blanket she’s had since childhood, being in her parents’ home, a dish she loves to eat…

Which of your skills or abilities are you most proud of?

What’s one dish you can’t make but wish you could?

Do you think bouquets should be all one type of flower, or a mix of a bunch of types?

  • With this question, make sure you take note of her answer! Not long after you ask it, be sure to buy her a bouquet that matches her description.

What’s the most transformative experience you’ve ever had?

Do you need an alarm clock to wake up, or do you normally wake up at a certain time?

What’s one trait you have that you think goes under appreciated by other people?

What’s the most trying thing you’ve ever overcome?

What’s one snack you would eat everyday if you could?

What would you do for a living if you absolutely had to switch careers tomorrow?

What’s the biggest/most expensive prize you’ve ever won?

Be honest: do you ever lie about your age? (And if so, where/when?)

Have you ever “put yourself out there’ and been rejected by someone?

What’s the biggest run in with the law you’ve ever had?

Would you rather be really famous and pretty rich, or pretty poor, but completely anonymous?

Should guys wear cologne?

How many selfies do you think you’ve taken in your life?

Are you a cat person or a dog person?

  • This is a good question to ask early in a relationship, especially if you feel strongly about one pet or another. (Or, like me, feel strongly about not having any pets at all.)

How often do you daydream or let your mind wander off?

How much screen time do you log each day on your iPhone?


34 Fun Questions to Ask Your GF

Smiling brunette couple having coffee
Finding a girlfriend who you can get to know on an intimate level – and who can get to know and appreciate you just as deeply – is one of the things that makes life worth living.

But after you’ve been dating for awhile and moved past the “honeymoon” phase of your relationship, it can also get a little bit… well, let’s say “less than fresh.” (I’m not going to say “stale” because my wife reads this blog.)

And because you’ve already asked all of the “getting to know you” questions, it can be hard to come up with new questions that keep things fresh, fun and exciting.

Use the questions below to touch on some topics of conversation you and your gf probably haven’t covered yet, which will not only help you get to know her better, but open the door to all sorts of new conversational possibilities.

The Questions:

Why did the parents choose the name ______ for you?

How would you react if a woman hit on you?

What’s the most kind gesture you’ve ever received?

  • You can follow this one up by asking her about the kindest gesture she’s ever given, too.

What’s your favorite way to Treat Yo’ Self?

If you had all the money in the world, where would you choose to live?

What’s your favorite karaoke song?

Who is one person who’s talent you wish you had?

What would you do if you had to choose one of these three for the rest of your life: wine, chocolate, coffee?

What would you do if you won 10 million dollars?

Name one thing you love about technology, and one thing you hate.

Who’s your favorite fictional character of all time?

Where would you rather live: Westeros, or Westworld?

What’s your least favorite pop culture phenomenon?

Do you remember the best compliment anyone has ever given you?

What’s the funniest joke you’ve ever heard?

  • If she can’t remember any jokes, ask her about the funniest thing she’s ever witnessed in real life, or the funniest scene she can remember for a movie.

What’s the hottest piece of clothing a guy can wear?

Are you a pack rat? What’s the weirdest thing you’ve held on to?

What was your favorite movie when you were growing up?

If you had to choose one food to eat for the rest fo your life, what would you choose?

What’s your absolute favorite board game?

What’s the best birthday party or birthday experience you’ve ever had?

What do you do when you want to feel sexy?

  • This could be something she wears, something she does to feel good, something you do to make her feel good…

What’s the one destination you most want to visit?

What song always – or almost always – brings you to tears?

What unhealthy food is your biggest guilty pleasure? What do you secretly love to pig out on?

What’s the best experience you ever had while working?

What’s one toy you used to play with as a kid that you wish you could still play with as an adult?

Tell me about your first kiss – when was it, who was it with, what were the circumstances?

What’s the best lesson you learned growing up?

Do you remember the name of your first crush?

If you could take a single pill to get all the nutrients you need, and never eat a meal again, would you do it?

Have you ever been/would you ever go to a nude beach?

What would you rather have: a mansion, a private plane, or a private yacht?

What’s better: a penthouse condo in Manhattan or a castle in rural England?


7 Questions to Ask a Girlfriend Over Text

Smiling man using smart phone
While asking open-ended questions that can spark longer and more in-depth conversations is generally a good idea, with text it’s a little different.

Writing out long answers via text can be tricky (and to some people even a little annoying), so when texting you don’t want to ask too many deep questions that would require long, drawn-out answers.

Instead, the best questions to ask a girlfriend over text are the ones that are interesting and unique, but easy for her to answer in quick, short bursts of typing.

The Questions:

Have you ever had a surprise party thrown for you?

What’s your favorite, go-to cocktail or drink?

What’s the most embarrassing picture you have on your phone?

  • If she describes the shot to you in words, you can ask her to send it to you. Just be prepared: she’ll probably ask you to do the same!

What’s the lamest pickup line you’ve heard? (Follow up: Have you ever heard a good one?)

If you were in Hogwarts, which house would you be in?

  • Questions like this are random, which is why they’re fun and engaging, in addition to being easy to talk about over text.

What’s the funniest GIF you’ve ever seen?

What would you rather lose: your phone, or your wallet?

  • “Would you rather” questions are great for text because they have short answers, but there’s virtually no end to the possible questions.

31 Deep Questions to Ask Your Girlfriend

Couple hugging intimately
While it’s important to keep things fun, flirty and engaging, one of the advantages of having a girlfriend is being able to get to know each other on a deeper and more meaningful level.

In addition to the above questions, it’s important to ask your girlfriend deeper, more intimate questions that will reveal more about who she is, who she wants to be, and what she truly feels.

The below questions will spark some deep conversations about topics that are more personal – and potentially more important – to her as a person.

The Questions:

Are you a religious or spiritual person?

What’s your take on soul mates? Do you believe there’s only one person out there for everyone?

Do you have a code of ethics that you follow?

Have you ever kept a journal?

Are you a decisive person, or do you prefer to let someone else make decisions so you don’t have to?

What do you prefer: spending time a lone or spending time with a big group of people?

Do you believe your dreams are trying to tell you something?

Would you ever consider adopting a child?

Was there ever a time when you experienced discrimination?

Have you ever attended a protest or rally?

Do you meditate?

When you’re sad, would you rather be showered with attention, left completely alone, or something in between?

Have you been in love before? How many times?

What words do you want other people to use when they describe you?

What’s one thing about your family that you don’t like and/or wish you could change?

What do you think you would want to do if you got pregnant by accident?

Do you believe that honesty is always best, or are there times when a white lie might actually be moral?

What’s your biggest ambition, goal or aspiration in life?

What’s one challenge of being a woman that men just can’t appreciate?

If you could live forever, would you do it?

What do you want your legacy to be?

Where do you draw inspiration? What makes you feel motivated to be your best?

What’s the single best piece of advice you’ve ever heard?

What intimidates you?

Do you have any traditions with friends or family that you hope to continue for years to come?

Are there any experiences or moments that you wish you could relive or do over?

If you could change one thing about the world, what would it be?

What do you think is the most important social cause facing humanity right now?

What makes you feel truly happy?

Did you have any ambitions as a kid that you now think are silly or childish?

Who do you admire most in the world?


Show Her Your Best Self

Woman looking at man with interest
Arming yourself with a long list of conversation-sparking questions to ask your girlfriend is a great way to show her that you’re interested and engaged in her as a partner.

Of course, if you’re like most guys, you also want to show her that you’re not only interested and engaged, but handsome and attractive. And for that you need to know how to nail the dapper details that make a man look sharp and stand out.

I’ve put together a checklist of the nine details you need to nail to look polished and put together. Enter your email address below and I’ll send you the head-to-toe checklist you can use to put your best face forward.

The (handsome) devil is in the details

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