The Deep Questions to Ask a Girl Every Guy Needs to Ask

Starting a conversation with deep questions to ask a girl

We all know I’m a fan of keeping things light and playful in the early days of dating. It makes for easier conversations and a fun vibe while you get to know each other. As things develop, “real” conversations will start to happen too. That’s where it can be helpful to have deep questions to ask a girl.

They’re a great way to get to know her better and to understand who she really is beyond the playful banter you’ve exchanged previously.

In this article, I’m going to run you through some simple questions you can ask to get that conversation going. As always, tweak them to suit your own personal style and see where it takes you.

Deep Questions to Ask a Girl You Should Know

These questions are designed as more of a springboard than anything else. They’re deep questions to ask a girl, not rapid-fire questions to bounce around with.

Each question can easily lead to its own deep conversation. Use them sparingly when the two of you are alone together and in the mood for deeper conversation.

1. What’s one guilty pleasure you love to do by yourself?

I find this to be a great question to get things started. It’s a simple, innocent question and the answer will give you a good idea of the type of person she is.

While our guilty pleasures don’t define us, they sure are a telling sign. Is she the adventurous type that loves to go outdoors in search of adrenaline? Maybe her guilty pleasure is Netflix and knitting.

2. If you could do anything in the world, what would you do?

As an avid traveler who’s always down for spontaneous adventures, this is a question that excites me.

You’ll soon find out if she’s the type who loves to explore the world or prefers the comfort of home. If she’s a traveler, is she the tour-bus type, a hitch-hiking jungle-trekking adventurer, or somewhere in between?

As a bonus, the answer to this question often launches into exciting storytime. Crazy travel adventures are fun to hear about and are sure to have her engaged in the conversation too.

3. What do you find attractive in a man? This is a deep question to ask a girl if she already trusts you.

So long as the two of you have been able to have open conversations like this already, this is a great question. Just be careful of your delivery on this one.

Confidence is a very attractive trait and this question has the potential to come off as seeking validation to have her tell you all the things that are great about you and how much she appreciates them.

Instead, this question is effective because it gives you more of an insight into what she appreciates and looks for. The things she’ll appreciate about you and those that she won’t.

Her answers shouldn’t be used as a prompt to change who you are by any means. You’re just getting to know what she likes!

4. What’s something that would surprise me about you?

Delivered with a playful, flirty vibe, this question can make for some very interesting conversation. A little more on the flirty side than the other questions, but that doesn’t necessarily mean it’ll go that route.

I would warn that this one is something to be saved for when the two of you have built strong trust. If she’s going to answer this question properly, she’s sharing something she wouldn’t usually talk about.

At the same time, the very act of sharing secrets between one another will bring you closer as well.

5. If money wasn’t a problem and you could travel anywhere in the world, where would you go?

In my experience, there are two types of travelers. The five-star hotel, all-inclusive, Insta-worthy types and those who prefer things to be more low-key.

This is a great way to get to know which of those she is. Although it won’t exactly tell you who she is, it will help you understand more about her.

Particularly if things start to get more serious and you begin traveling together. You can get a sense of how well the two of you could do that and if you’d both agree on a destination.

Would she insist on the oceanside huts of Bora Bora or prefer to lace up the hiking boots and explore glaciers in Patagonia?

At the very least, knowing her answer to this question can help you plan surprise adventures in the future.

6. What’s the craziest thing you’ve ever done?

I love this deep question to ask girls and the conversation that follows. It always leads to some exciting storytelling of adventures you never would have expected.

I’ve heard responses that have ranged from getting lost in the jungle to being kidnapped in Vietnam and everything in between.

Strap yourself in for this one and get ready to be shocked because even the most mild-mannered of people will surprise you with the things they’ve experienced. To me, that’s half the fun!

As a bonus, if she’s more on the reserved side, this can be a great way for her to open up as well. Once you know some of the wild things she’s been up to, the bar has been raised a little for further exploration.

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7. What’s something you’ve always wanted to try?

The perfect follow-up question to the one above, expect to be surprised once again.

Although my tastes have changed more recently, I used to lean toward the straight-cut, professional type. You might expect the lawyers and accountants of the world to have some tame responses to this question.

That, gentlemen, is why stereotypes are such a bad thing. Some of the answers shocked and intrigued me and I’m sure you’ll find the same.

Since her answer will likely be something she’s passionate about, don’t be afraid to ask more questions either. A simple “why?” can lead you both down a fun and engaging tangent.

8. A deep but lighthearted question to ask a girl: What makes you laugh the most?

Humour is something that matters in all levels of dating. Whether it’s a simple hookup or a long term relationship, being able to make each other laugh is important.

If you can better understand what makes her laugh, keeping that fun element alive is much easier. That said, I wouldn’t suggest changing your sense of humor to suit her.

I’m a strong advocate for staying true to yourself and your own personality. Certainly for me, my particular brand of humor is a big part of my personality. To change it would be to change who I am.

Instead, just remember there’s a time and a place for certain jokes. Her answers to this question will help you pick that timing better.

9. What’s your favorite thing about yourself?

This is another question that should be saved for when the two of you have built a lot of trust. Even on a list of deep questions to ask a girl, this can be more of a personal question than you might realize.

More often than not, you’re going to learn a few things from the conversation that follows. You’ll get a better understanding of her confidence levels and her insecurities. Of course, you’ll also learn what she likes about herself the most.

These elements in themselves should never be underestimated. On top of that, you’re getting a better picture of where to tread lightly and what you can openly appreciate.

Compliments and constructive feedback in a relationship are important. This question can help you better understand how to use them both effectively. The last thing you want to do is accidentally draw attention to something she’s already insecure about, right?

10. What has been your proudest achievement?

To finish off this list of deep questions to ask a girl, this one intrigues me. It’ll help you understand what she really values both in her personal and work life.

For some, it might be monetary. But for others, it could be power, knowledge, altruism or any combination of these.

Learning what others take pride in goes a long way to understanding their personality type in general. It lets you know the types of things they value in life and what motivates them to do more.

Asking a Girl Deep Questions Can Bring You Closer

With this list of deep questions to ask a girl, you’ll get a far better understanding of who she is. What motivates her, what she’s proud of and what she really enjoys doing.

Of course, be ready to answer each of these questions in return as well. When you can both share so openly and understand each other on that level, your relationship will benefit.

I wouldn’t suggest running through this list all at once. Instead, use these questions sparingly and in a context that makes sense. Most of all, enjoy really getting to know her!

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