Regardless of if you’re in a relationship, dating, or you’re digital pen pals, impressing a girl you like has never been an easy job. Let’s be honest. There are so many things you need to pay attention to. 

That little voice in your head is probably sick of your modern dating endeavors and constantly reminding you of the following: 

“Stay away from overusing those emojis! Don’t initiate a date when it’s too soon. Don’t tell her too much info about yourself but also don’t be reserved. Be a gentleman but don’t put her on a pedestal.”

Seriously, if I were a guy, I would probably give up on dating and courting women immediately. Joking aside, it would be unrealistic to say that only the male species overthinks when it comes to these things. 

Women are pros at overthinking and inventing problems (especially in relationships), which makes us, in a way, equal (minus the Venus-Mars theory). 

I’m sure I’ve impressed you with my babbling skills, but this is not why you’re here, right? You’re here because you want to impress that one special girl. Do you want to get to know her better as well?

Then I might have something for you. The easiest way to achieve these two things is by asking her MEANINGFUL, DEEP, and FLIRTY questions!

Fellas, it’s time to step up your flirting game!

a man and a woman sit and talk

What does flirting mean to you? Does it mean sending flirty emojis, GIFs, or similar? Or do you see flirting as teasing her like a boss?

Well, there’s no right or wrong answer here. There are many different ways of flirting, and the best thing to do is combine them. 

Yes, this means that you shouldn’t only rely on flirty pick-up lines but also include other powerful flirting techniques such as FLIRTY QUESTIONS.

If you ask me, flirty questions are ten times better and safer than flirty pick-up lines because it’s relatively easy to potentially insult her with the latter. 

With all that being said, here are some flirty questions to ask a girl you want to impress:

  • If you could spend an entire day with me, how would it look?
  • Have you ever done something in a public place that you probably shouldn’t have?
  • How would you react if I told you that I like you?
  • What are the top items on your bucket list?
  • What is your biggest turn-on in a guy?

When thinking of flirty questions, just make sure that they are interesting enough to catch her attention. Here’s some humble advice from a female (me): 

If you want to impress a girl, avoid asking her questions that require only 2 seconds of her time to answer. That means her reply will be mechanical, and you will not make her think.

In other words, you will not impress her, and you will not learn anything new about her. So, step up your game and be creative when it comes to thinking of the right questions to ask.

INTIMATE and DEEP questions are your best friend!

a man and a woman sit on the couch and talk

If there’s anything I hate in the world (and I mean really hate), it is generic, random questions asked by guys. Please, don’t start every conversation with: Hey, how are you? What are you up to? (This applies to both virtual and real-life conversations).

You see, when you keep forcing this generic small talk, I instantly start thinking that you’re not as interesting as I might have thought in the first place. I’ll classify you as one of those ultimately boring guys because of whom I need to fake a call (or engage my friend to do it) only to save myself from a bad date. 

Don’t be that guy. Be curious. Be thoughtful. Be interested in deep conversations and a variety of topics. 

I’ll tell you one little secret about these conversations. If you’re not enjoying it, then you know you’re not doing it right. You can’t just memorize a list of questions and throw them at her in alphabetical order. 

You have to feel these questions and, more importantly, you have to be interested in her answers. Follow-up questions are your runner-up best friends! 

Asking the right follow-up questions means that you were listening carefully to her and that you have the capacity to keep the conversation going like a boss. Every girl will appreciate and love that.

If we see that you’re actually making an effort, we’ll classify you as “worthy of dating” or “worthy of being in a relationship with.” If you want her to see you in that light, then consider asking her these intimate questions:  

  • What would you change in your life?
  • What is your biggest achievement?
  • What is the thing you are most afraid of?
  • Is there something in your life you really want to do but haven’t done because you are afraid?
  • If you could buy a one-way ticket to any location in the world, where would that be and why?

Do you want to explore her mind? Do you want to learn about her dreams, wishes, life choices? Of course, you do! Even if you don’t want to, you have to pretend that you do because how else are you going to win this lady’s heart?

If you want to court her like the true gentleman you are, you need to ask her the right questions that will accentuate your qualities. 

To simplify, you need to let her know that you’re not just some random guy who is only interested in drinking beer with his buddies and asking questions on a 10-year-old boy level.

Well, even if you are, you have to pretend that you’re not because how else are you going to catch her attention? Truth be told, some girls are attracted to guys who are overly casual and have no particular interests or ambitions, but most aren’t.

Don’t worry, here are some deep questions to ask and explore someone’s mind to the rescue:

  • In your opinion, why do people stay in toxic relationships?
  • If a crystal ball could tell you the future, what would you want to know?
  • In your opinion, what is the meaning of life, and why are we all here?
  • What are the biggest obstacles that we face while achieving our goals?
  • Do you think that there are negative emotions, taking into consideration that every emotion has a purpose?

If any of you guys asked me some of the questions mentioned above, I would be one hundred percent amazed by your level of thoughtfulness and intelligence. So, I’m sure every other girl would experience it in the same way.

Discover the magic of pillow talk questions!

a happy couple in love lying in bed and talking

Whenever I think of pillow talk, I instantly get these warm fuzzy feelings because it’s one of the most beautiful things in the world. 

Snuggling next to your loved one, stealing their warmth, and having deep conversations is something that will never get old. 

I don’t know about you, but every time I go to sleep, I start analyzing and overanalyzing everything. I think about the meaning of life, alien invasions, the pursuit of happiness, and plenty of other things that interest me.

The best of all is that pillow talk usually turns into a laughing session towards the end because when you’re feeling relaxed, it’s really hard to keep concentrating for a long time. 

Well, that’s the beauty of pillow talk. If you’ve never practiced it, now is the perfect time to do so.

Here are some fun pillow talk questions to ask your partner in bed

  • What was your impression of me when we first met?
  • Is there a song you hear that makes you think of me?
  • What’s the most embarrassing thing you have ever experienced?
  • How would you describe me in three words?
  • If I got into any kind of trouble with the police, would you be my alibi?

“Improvisation is the power of spontaneous observation.” – Wyatt Pringle

a man and a woman smile and talk while sitting in a cafe

Feel free to improvise with different concepts, ideas, and questions. You cannot go wrong with it. Add a joke or two to the equation, and there you have it: A recipe to impress any girl out there. 

Impress her with your ability to think outside the box, to connect the unconnected, and to get out of your comfort zone. Deep conversations are like a prelude to a book (descriptive of what is to come).