Dating Tips > First Dates > 30 Charmingly Flirty Questions to Ask on A First Date

30 Charmingly Flirty Questions to Ask on A First Date

Flirty questions for first date

If you are planning your first date, it's natural to feel nervous. Nobody wants to ruin the chances of getting together with someone they like. However, it can be tricky to impress a stranger, that too in the first meet. You have no idea about what kind of a person they are.

There are many wrong moves that can lead to a disastrous first date. You may run out of topics or your conversations may even get awkward, but you must keep the other person engaged. The easiest trick to charm your date is to ask them flirty questions. This will help you know them better and at the same time, you can determine how interested they are in dating you. If you ask the right questions, it can even get them closer to you.

1. How you doing? (Joey’s style)

If you are a FRIENDS fan and so is your date, this is the perfect opening line for your first meeting. Just make sure you do it right in Joey’s style. If you have seen the show, you’d know how effective these three words can be. Just be confident, look them into the eyes, nod your head, and ask them with a smirk, "How you doing?"

2. How would you define a perfect date?

It’s good to ask someone what’s their idea of a perfect date to gather useful information for all your future dates. Also, it will give you an idea as to how different or similar the two of you are when it comes to romancing a partner.

3. Who do you think about a girl making the first move?

Many people think that guys must propose to their lady in a dreamy, romantic manner as girls don’t prefer taking the lead in such matters. However, there’s no such rule. People are free to act on their thoughts irrespective of their gender. And it is high time to break the gender stereotypes. So, ask this question to give your partner a clue.

4. What attracted you most about me?

If someone agrees to go on a date with you or asks you out, they must have liked you for something. Won’t you be curious to know what made them notice you or what did they like about you? So, go on and ask them. It will be a good topic to strike a conversation; you’ll get to know what’s on their mind and what they really think about you.

Flirty dating questions

5. Do you have a dirty secret?

There’s nothing like sharing some weird and crazy stuff with a stranger. Sometimes, you can’t tell your secrets to your folks fearing that they might judge you, but you can tell them to a stranger because they barely know anything about your life. This question will spice things up and make the date exciting for the two of you.

6. Have you ever done something socially unacceptable in public?

We all have a past that we are not proud of. This is a fun question and will unravel the fun side of your date. If you want to share a lighthearted moment with your date by sharing an embarrassing memory and have a good laugh about it, make sure to include this topic on your first date.

7. How important is it for you to have a kinky partner?

To bring the date back on track, ask them something intimate. If you are into kinky stuff, you’d want to know about the other person’s thoughts. It’s not only fun but also important to make sure that you both have something in common. However, pick the right moment otherwise it will just make the conversation very awkward and will creep them out.

8. What’s the weirdest place you’ve fooled around with someone?

Once your date gets comfortable in sharing things with you, they won’t mind you asking such questions. Besides, they may ask you the same, leading to some interesting reactions and discussions.

9. What’s your wildest fantasy?

This one is yet another interesting question to ask someone you like. It will help you get closer to them and would reveal a part of them that they don’t usually share with anyone. If they decide to answer this, it’s a sign that they are having fun with you and there are no judgments in that moment, which is exceedingly rare.

10. How was the experience of your first kiss?

First kiss is always memorable for obvious reasons. It might not be pleasant for everyone but it’s mostly worth talking about. It’s a great question to ask on a first date, if the other person is comfortable talking about it. And if they aren’t, just switch to another topic and go with the flow.

Flirty questions you can ask your date

11. Have you ever kissed on your first date?

Feel like kissing on the first date but afraid to make the move? No worries! Just ask them about their opinion on kissing on the first date. Their answer will be enough to indicate whether you should act on it or drop the idea.

12. Would you rather enjoy a spontaneous kiss or a planned one?

It’s tricky to find a balance between respecting boundaries and savoring the moment. A spontaneous kiss can be extremely romantic, but both the people should be ready and okay with the act. No matter for how long you have been thinking about it or how quick you are to seize the moment, the implementation matters a lot. So, ask your date what they would prefer and act accordingly.

13. How are you still single?

This question will not only bring a smile on their face but will also boost their ego. They will feel confident and would appreciate you for acknowledging this fact. It might appear as a form of flattery but overall, it can be looked upon as an innocent attempt to flirt.

14. How do you stay so fit?

If you want to complement their body, you can indirectly use this question just to emphasize how interested you are in knowing about their healthy lifestyle and fitness routine. People who are fitness freaks, love talking about a healthy lifestyle and will also feel rewarded. However, if they are not into fitness, this question may make you seem judgmental. So, choose your questions wisely.

15. Did you inherit your good looks from your mom or dad?

This is yet another way to complement someone. It would mean you are not just appreciating their looks but also complementing their parents. In a way, you would appear interested in connecting with them beyond this date.

16. How easily do you get turned on?

Ask your date what turns them on, so you know how to get their attention. Make sure that both of you have gotten to a point in the conversation where you can discuss such topics. Otherwise, it can look like an unnecessary attempt to creep them out.

Flirty questions to charm a girl

17. How do you know that someone’s into you?

If your date is smart enough to get hints, they would know what to expect when you ask this question. When you really like someone and you can’t say it directly, you can use such questions to drop hints and keep the conversation exciting.

18. What do you like most about dating?

When you are meeting a stranger for a date and you don’t want to ruin your chances by asking risky questions, ask them this question. Their answer might indicate what’s on their mind and what are their intentions. They may unravel how often or how rarely they go on dates which can be a useful information for you, ngl.

19. What’s the first thing you notice in a person?

The first thing a person notices in their date says a lot about them. With this answer, you’ll get to know whether your date has noticed how you look or how much effort you have put in dressing up for the date. It will also clarify their general perception of people.

20. Do you think love at first sight is possible?

Isn’t the concept of love at first sight too filmy and yet romantic? Well, you’ll know if both of you are on the same page regarding this concept once they answer this question. If they do believe in love at first sight, they might also tell you how they felt when they first saw you. That’ll be an interesting conversation, don’t you think?

21. Do you believe that everyone is destined to meet someone special?

This one is a witty question that you can use to know whether your date is a hopeless romantic who adores 'made for each other’ kind of concepts or not. If they believe in such stuff, chances are they will be taking the relationship seriously and are not looking for any flings.

22. Do you think opposites attract when it comes to dating?

While some people look for partners with whom they can find shared areas of interests, some fall for extremely opposite personalities. You can ask your date whether they get attracted to opposites so that you two getting together isn’t an issue for them irrespective of the differences in your personalities.

23. What do you think about cheesy nicknames that people give to their partners?

People often use romantic nicknames for partners; these can be cute or embarrassing. This is a great topic for a conversation as it will be interesting to share funny stories on a date so you two can share a laugh and say goodbye to the awkwardness.

How to flirt on a first date

24. What’s your opinion about PDA?

It’s flirty yet important to ask your date what they think about PDA i.e., Public Display of Affection. Won’t you want to know how their social media account would look like if you two get together. If you aren’t into PDA and you don’t want them to post any pictures on future dates, this is your chance to tell them.

25. What’s the cheesiest pickup line you have ever used or heard of?

We all have heard certain cheesy pickup lines at some point in our life. This is a relatable topic to discuss on your first date as it will unveil the fun side of both pf you. You can share some cheesy moments from the past and laugh out loud, thus easing the situation.

26. How often do you like to try new things?

With this question, you’ll get to know if your date has the potential of turning into something long-term. If you get bored of things too often, a partner who likes trying new things will be very much compatible with you.

27. Do you think emotional intimacy is important for physical intimacy?

Usually, girls need emotional connection before they get intimate with someone while guys don’t necessarily want any emotional involvement when they are looking for a fling. This question will clear all your doubts and will ensure where both of you stand regarding intimacy in relationships.

Tips to flirt on a first date

28. How old were you when you dated for the first time?

This question will take the conversation back to the early days of your lives when you just started to date. Not only will it be fun to talk about but it will also bring a smile on your faces through a flashback of all the memories.

29. What do you think about casual flirting?

If you feel like flirting on your first date and you can’t tell whether they are getting the signal, ask away this question. It will help you understand how much your date knows about dating and where to draw the line when flirting with someone on a first date.

30. Where do you think this date is going?

It’s not like you are talking about the prospects of a relationship and enquiring about the future. “Where this date is going,” is just a harmless query to understand what the other person thinks of you. Their answer will tell you whether they have already started liking you or will they need a few more dates to develop the same feelings as you have for them.

Contributor, December 7, 2020

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