20 Flirty Questions To Ask A Girl When Dating (And Not To Ask)

Last updated on : February 01 2021

Smiling girl flirting

You can split the best flirty questions to ask a girl when dating into two categories: 

(1) Qualifying questions that help you find out if she's the right girl for you. And (2) questions that cheerfully prod and tease her into liking you more. 

In this guide, we'll provide ten examples of questions from both categories, with clear reasons why you need to ask them, and in what context. And we also provide example questions that you should avoid asking. 

What is great about these questions is you can use them while texting, in person conversation, or even on a dating app (if you're new to online dating, check out this review of the best dating apps in 2021 from Beyond Ages). 

A. Ten Flirty Questions To Determine If She's The Right Girl For You 

Guy flirting closely with girl

If you want to check that your crush is a strong, confident woman before you agree to progress things further with her, you can use the following questions, or variations of them, to determine whether this is the case.  

We've noted in brackets after each question why you need to ask it or similar. You'll see that the questions line up perfectly with the qualities we think you should look for in a potential partner.

Although these might sound like interview questions, and potentially some might seem rude too, you don't want to come across as if you are conducting an interview or being insincere. 

Instead, build these questions into the conversation over time, keeping it fun and light. Be a little cheeky when asking them, and ensure the fun factor and your date's engagement levels remain high. 

Also, You don't need to ask all the questions on your first date either. As long as you feel you are making progress, you can take some time to get through them all.  

Question 1 - Do you like to do things for others without being asked? Can you give me an example of when you did something like this and how you felt when you did? (Ask this question to understand whether she is giving in nature). 

Question 2 - Are you generally on time for meetings and appointments, or are you often late? (Ask this question to understand how responsible she is). 

Question 3 - What are you like when you get angry? Are you the "silent when angry type," or do you fly off the handle? How easily do you lose your temper? (Ask this question to understand how emotionally stable she is.)

Question 4 - Do you like doing new things, or prefer a routine? Can you give me an example of when you pushed outside your comfort zone and how you felt when you did? (Ask this question to understand how agreeable she is). 

Question 5 - Have you ever stolen anything from anybody, and can you share the experience? If you were all alone and would never get caught, would you steal candy from a baby? (Ask this question to understand whether she is trustworthy). 

Question 6 - How do you feel about trust in a relationship? Do you get jealous quickly, or are you happy to set your lover free? (Ask this question to understand how dependent she might be on you or whether she is needy). 

Question 7 - What are you struggling with in life? What is your most immense hardship that if you had a magic wand, you'd disappear immediately? What would you do if you won $10m in the lottery tomorrow? (Ask this question to understand what baggage she might be carrying, like excessive debt or other commitments).  

Question 8 - How much exercise do you get? And what are your views on dieting? (Ask this question to understand how your attraction to her might change over time). 

Question 9 - When last have you had a boyfriend? What is the best and worst part about being single? (Ask this question to understand whether she is available for a romantic relationship). 

Question 10 - Do you read books or prefer audio? How do you feel about learning new things about your career or life in general? What do you think is more important, being pretty or being smart? What is your biggest passion, and why? (Ask this question to understand what life desires she has and how she feels about personal development).  

Yes, these questions might come across as a bit rude and bitchy, even if asked with a smile. That's because they are.

If you're not going to throw a few hoops for a woman to jump through, you're going to end up going on dates with a lot of weak and spineless women.

Just be sure you ask them in a fun and non-threatening flirting manner, and you'll soon separate the women who are interested from those that want attention. 

You'll be able to see who is genuinely confident and who is all bravado and whether she demonstrates the qualities that men find attractive in women aside from their looks

B. Ten Flirty Questions To Make Her Want You

Young attractive couple with girl blushing

Below are some excellent additional questions to ask once you've decided that this girl is the real deal and want to spend more time with her.  

If you ask a woman these following questions, she might choose you over the man who was too proud to ask them (even if she liked him more). 

She might choose you because these questions employ techniques like push/pull, disqualifiers, and cold reading that pique her interest and leave her wanting - see below for an explanation of these techniques.

Question 1 - Thank you for making an effort for our date. Your hair looks beautiful today? 

This simple question is a genuine compliment but also leaves her asking for more from you, in her mind, of course - "What does he mean my hair looks beautiful today? Did it not look beautiful yesterday? What do I need to do to have it looking beautiful for him tomorrow? These thoughts will leave her wondering about you.

Question 2 - How did you get so funny/intelligent/charming?

This rhetorical question lets her know you appreciate a particular aspect of her personality. It's refreshing for her as most men will be focussing on complimenting her looks.  

Question 3 - Are you a good kisser? 

If she's attracted to you and has an ounce of confidence, she should take this question as her cue to kiss you. 

Question 4 - I love the way you think. Are you always so sexy with your words or thoughts? 

A man knows that seduction is not about physical appearance only. It's so much more about intelligence and wit, and it's about finding someone who can make you laugh. This question demonstrates you understand real seduction.  

Question 5 - What's your view on sex? Do you think sex is something couples should talk about first?

If you can find a way to bring sex into the conversation and she's open to it, then you are halfway there. However, don't linger on this conversation but instead, leave her wanting for more. 

Question 6 - Do you think you're cute?

Ask this one as a challenge, almost like you are disapproving. You want your date to be slightly on the back foot. Then you can respond with a smile and a "Well. I think you are today." Don't forget to add the today, as this softens the compliment, which is essential to do. 

Question 7 - Do you always drop things/mix things up? We can't take you anywhere, can we? 

Say this when she drops something on the floor, foibles her words, or gets confused. It's a cheeky question designed to push her a little. To be successful with this question, you must follow immediately with a smile to let her know you are joking. 

Question 8 - Do you work out?

This question seems innocent enough on the surface, but what you're communicating is that you appreciate the effort she makes to look good. Give her bicep a playful squeeze for extra points.  

Question 9 - Can I kiss you? 

It never hurts to ask, and a man is never scared to do so. But make sure you do so at the right time, and always respectively.

Question 10 - Will you come to my room/on a date?  

It sounds crass, but asking for what you want is a sign of strength and masculinity. A man knows what he wants and is willing to take it. Of course, when asking these types of questions be respectful, and always consenting. 

C. How To Deliver The Questions

Intersperse these ten questions with the ten qualifying questions outlined at the beginning of the article. When used together, you are well armed to keep your date engaged in conversation about herself - while achieving your aims of getting to know her better and leaving her thinking positively about you.

Don't talk about yourself unless asked directly, and even then, don't offer up too much too quickly. Let your date discover you slowly. The more she talks about herself, the better for you.    

If you do it well, your date will also worry less about getting "pumped and dumped" given the genuine interest you show in her - unlike most other men who will try to win her favors with compliments or gifts and by talking more about themselves. 

And do whatever you can to get her experiencing a wide range of emotions (even sadness and anger). Throw in some old stories (fun, sad, or exciting ones), and use a balance of push-pulls, disqualifiers, and cold reading techniques (see below). 

If you do it well, you will show healthy internal strength, confidence, dominance, and a lack of neediness while hooking her more towards you.

D. Questions Not To Ask

Girls listen to their emotions more than men and judge you based on how you make them feel. Your job is to avoid saying anything that can turn her off

So, less is more when it comes to "deep or quirky questions." 

Connect with her in a fun and playful way. Don't ask quirky questions that put her on the defensive, or try to connect with her too deeply. 

Here are some examples of questions to avoid: 


  • Why did you break up with your last boyfriend? (Too deep too soon)
  • What are your plans for today? (She wants you to lead, and leaders don't say that)
  • Where do you want to go? (Same as above)
  • How come you're X age, and you're still single? (This is not a compliment)
  • Did you cheat on your ex? (Rude and too deep) 
  • Any question that makes her feel her life is a mess - like, "how come you're 40 and still waiting tables?"
  • How many guys have you slept with you? (Rude and invasive)
  • Are you religious? or Why do/don't you believe in God? (Too deep?)
  • How much money do you make? (Too personal?)
  • Are you having fun? (Can make you seem insecure or needing some assurance)
  • Do you like what I'm wearing? (No self-confidence)
  • Do you like me? (No self-confidence)
  • Where do you see this going? (A man should never ask this question)

E. Conversational Techniques

Learn these conversational techniques to keep your date interested in you and slightly unsure about your interest levels. This state will keep her engaged and wanting more of you. 

1. Push Pulls

A push/pull is a complement (the pull) follow by a negative (but not insulting) comment (the push). Or the other way around. You must always follow them up with a smile or similar gesture, so she knows you are joking.

  • Those professor glasses are cool. Are you trying to be sophisticated (Or, those Harry Potter glasses look cool on you)
  • I like your anklets/bracelet. Wait a second. You really have very small hands/feet.
  • That top makes you look cute, just like a cute minion.

2. Disqualifiers

Disqualifying yourself tells her, "you're not hugely interested," and so they make her want you more.

Some of these lines are:

  • You're not getting into my pants tonight.
  • I'm too shy/cute for you.
  • You and I won't get along pretty well.
  • You're a lousy hugger, although I could learn to like it. (This one is a push/pull too)  

3. Cold Reading

Cold reading is an easy way to build the "OMG. He understands me so much" vibe with her. All you need is to listen (which is the most challenging part) and reflect on what she says. 

For example, if she tells a story that compliments her mom/dad about something. Rephrase what she says with something like, "you seem to have a strong connection with your family..not all girls have that."

If she says something about cooking, try to guess whether she is a good cook or not, and what her favorite food is. If you get it right, you'll astound her. If you get it wrong, turn your mistake into a compliment. 

F. Conclusion

Couple together in sunset

When dating, flirtatiously ask questions that both help you understand whether your date is a good fit for you and questions that pique her interest in you.

But always remember to deliver your conversation in a fun and light-hearted way, avoid anything too deep or negative, and employ conversational techniques like push/pull, disqualifiers, and cold reading.

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