Flirty First Date Questions To Get Women Interested

In Depth Reading Time: 12 minutes
best first date questions to ask women and get them attracted

Don’t know what to ask women during dates?

If you want to keep the vibe flirty, juicy, sexy, and downright fun during the first date you’ve got to know what to ask.

Forget the mundane “get to know you” stuff – that’s not how you spark a connection with girls.

If you look at the majority of the questions below, they’re not under “get to know you” questions.  

You want to leave those boring lines behind and get her smiling, laughing, and, most importantly, thinking about you long after the date.

Because as we talked about in an article before. It’s much better to flirt and attract first, make it like the major thing. Then a few here and there get to know her.

Here are the things you should talk about to women on the first date: What To Talk About On A First Date

So, here’s the deal: I’m going to share some questions to ask on a first date that are all about setting the stage for attraction. And they don’t need to sound robotic, or rehearsed either.

We’re talking questions that are playful, a bit bold, and totally unexpected. Because remember, we’ve already gone over the basics in a previous article. It’s time to crank up the charm and make a lasting impression.

Tips For Best First Date Questions

Focus on flirting and attracting

When it comes to getting to know a woman, it’s pretty straightforward— you just ask her, right? But capturing her interest and keeping it? That’s where the real challenge lies.

One, the first date, your focus should be on flirting and creating attraction right from the start.

Our flirty questions to ask on a first date are designed to do just that.

By using flirty first date questions, you can create a playful atmosphere that encourages both of you to open up in a fun and engaging way.

Flirting is an art, and like any art, it requires practice and finesse. So when you go on a first date tonight, use these, and the again, soon you’ll know how it all works.


Here’s why I’m sharing this advice. I once went on a date with a total bombshell, the kind of woman who turns heads everywhere she goes. I couldn’t believe she agreed to go out with me.

The date seemed to go well, and I learned a lot about her, but that’s where it ended. I realized I didn’t even get to flirt with her; it felt like I was just having a conversation, not a date.

That’s why these flirty first date questions are so important—they give you the perfect opportunity to start flirting right from the start of talking to her.

Substance over surface

If you’re looking to truly connect with her, skip the usual, mundane questions about favorite food or movies.

I mean, aren’t you tired of getting asked what you do for a living or where you grew up? Yeah, those are basic questions, but you can word them better, or ask them at the right time.

Instead, of boring first-date questions, ask questions that reveal her personality and values.

This not only shows genuine interest but also sets the stage for a deeper, more meaningful conversation.

Dive into topics that matter; ask about her life experiences, dreams, and passions.

The best questions to ask on a first date are those that help you understand the person behind the profile, giving you a real sense of who she is.

Ask without Interrogating

These questions are crafted to evoke emotions—feelings of lust, desire, romance, and fantasy. You don’t want to spoil the mood by coming across like a detective interrogating a suspect. Keep it light, playful, and engaging.

Use fun first date questions to keep the rhythm going, allowing for moments of laughter and surprise that can lead to a genuine connection.

Always have an answer.

While we’re talking about fun and flirty first date questions, it’s important to remember that the conversation should be a two-way street.

There will come a time when she’ll want to know your story. That’s why it’s crucial to have an answer ready.

Here’s a tip: it’s your story, so you can tell it how you want. Whether it’s embarrassing, exciting, or anxiety-inducing, the key is to make it engaging. You want her to be eager to hear more.

Avoid making your story self-deprecating; even in storytelling, you should present yourself in a positive light. After all, it’s still the first date, and you should aim to impress.

So let me ask you this. When your hot date asks about what you do for a living, do you just straight up give a dull, straightforward answer? “Oh, I’m into plumbing,”

Or do you turn it into an opportunity to showcase your passion and personality?

Instead of just stating your job title, try adding a personal touch. Talk about why you love what you do, or share a memorable experience related to your job.

“So, I’m fixing this leaky pipe in this lady’s bathroom, right? Out of nowhere, the husband storms in with a shotgun, sees me under the sink, and thinks I was there to fix more than just the plumbing! I had to do some serious smooth-talking to explain the situation and assure him that I was there purely for “professional” reasons and not to steal his wife!”

This not only makes the conversation more interesting but also gives her a glimpse into your world and what makes you tick.

Keep a list of backup conversation topics

The goal is to keep her interested and the conversation flowing. But if she starts to run out of steam or gets bored, it’s up to you to steer the conversation back on track.

That’s where having a list of topics to fall back on can be a lifesaver. You don’t have to memorize them all, just keep them in mind as options to explore if your mind goes blank.

Think of it as your conversational toolkit, ready to repair any lulls and keep the sparks flying.

Filter and Categorize

It’s okay not to have common ground.

While shared interests and common ground can be great, they’re not always necessary.

By asking these questions, you’ll get a glimpse into her values and outlook on life, which can be just as telling.

This can help you decide if there’s potential for a future together, regardless of whether you share the same hobbies or not.

If maybe there are differences, It’s perfectly acceptable to communicate your intentions for a more casual or friends with benefits relationship if that aligns with both of your desires.

It’s also worth being polite and open with women who are lukewarm or indifferent, as there may still be potential for a connection to develop.

Using your time wisely by focusing more on women who are enthusiastic about getting to know you can help you filter and categorize potential partners based on mutual attraction and connection. Our fun, flirty first date questions can do just that.

Sometimes, it’s the differences that make things interesting and give you both the opportunity to grow and learn from each other.

Unlock the Strategies

Fun First Date Questions

fun first date questions to make women interested

Initial Questions

Your first, first date questions should be light to break the ice and establish a comfortable atmosphere.

These first date questions are perfect for starting the date on a friendly note, just to get things going and to get her talking.

You want women talking on the date, and you can use these questions to avoid awkward moments at the start or gather some info you could use later.

  • How was your day today?
  • Are you excited?
  • Are you nervous?
  • Have you been to this place before?
  • Did you have any trouble finding this place?
  • Do you prefer coffee, tea, or we could go elsewhere and grab a bite?
  • Do you get bored easily?
  • Do you easily get distracted?
  • Are you superstitious?

Dating Life Questions

As the conversation progresses, you can delve into dating life questions to gain a deeper understanding of her past experiences and what she’s looking for in a relationship.

These questions can include asking about her best and worst dates, as well as what qualities she values most in a partner.

This can help you gauge if she’s a serial dater, if she tends to toy with men, or if she might play with your feelings.

It can also give you insight into how easy or difficult it might be to form a deeper connection with her.

Additionally, you can learn about any potential competition you might have and how to differentiate yourself.

Hey, women find it fun to talk about their dating life. They talk about it all the time with their friends, and their all smiles and giggly. That’s the vibe that she should feel from you.

  • How’s your dating life been going?
  • What made you go out with me?
  • What is your genuine first impression of me?
  • Did you stalk me on social media before we went out?
  • What’s the most fun date you’ve had recently?
  • What’s the worst date you’ve ever been on?
  • How did you two meet?
  • Did you do anything special on your last date?
  • Did you do anything naughty on your last date?
  • What made that date stand out from the others?
  • Do you see a potential for a second date?
  • How do you manage dating multiple guys?
  • Anything in particular you’re looking for?
  • What’s the first thing you noticed about me?

Romance Questions

To add a touch of romance to the conversation and make her envision romantic moments with you, consider asking questions that evoke feelings of love and connection.

These questions should be more personal and intimate, such as asking about her idea of a perfect date or what gestures she finds most romantic.

By focusing on you in her responses, she’ll naturally associate these romantic thoughts with you, helping to create a deeper bond between you and setting a romantic tone for the rest of the evening.

Additionally, discussing not only future romance but also past romantic experiences, such as relationships with exes, can provide valuable insights into her personality and how she behaves in a romantic relationship.

Digging deep into her past can reveal aspects of her character that will help you understand how she is as a girlfriend.

  • When was your last relationship?
  • Why did you guys break up, if you don’t mind me asking? (Oh I thought he couldn’t satisfy you.)
  • Ever been involved with a guy who already has a girlfriend?
  • What’s something you’ve always wanted to try in a relationship but haven’t had the chance to yet?
  • Do you kiss on the first date?
  • Do you fall easily?
  • Ever slept with someone on the first date?

Intimacy Questions

As the date progresses and you feel more comfortable with each other, you can explore intimacy questions to deepen your connection.

These questions can be more personal and revealing, such as asking about her thoughts on physical intimacy or what she values most in a partner.

At this time there’s no sex talk yet, you’re still easing your way in. It’s like, you know you want each other, but you’re taking the time, but still you’re about to go there.

This can help you understand her on a deeper level and strengthen your emotional connection.

  • Do you have any tattoos?
  • Do you prefer kissing or cuddling?
  • Do they say that you’re a good kisser?
  • Can you rate how good of a kisser are you?
  • Are you into casual flings?
  • But, have you had casual flings?
  • Have you ever had a casual fling that ended up becoming more serious?
  • How do you feel about public displays of affection?
  • Have you ever had a crush on someone you shouldn’t have?
  • Do you think it’s possible to be friends with benefits without catching feelings?

Role Reversal Questions

Hey, when women go on a date with me, sometimes they ask me questions that are like trap questions. You know, the ones where no matter how you answer, you’re kind of trapped?

Like, ‘Is it safe to ride with you in your car?’ I mean, why ask if you’re already getting in, right?

Anyway, you can turn the tables and ask these kinds of questions to catch them off guard. No man is asking them these questions, so it’ll make you stand out.

But remember, use them sparingly. If you ask too many, you might come off as egotistic or boastful.

You want to ask these questions when she says something funny, and they should result in making her smile. Timing is key here.

  • You’re not just trying to get me drunk, right?
  • You’re not just interested in the physical stuff, are you?
  • You’re not going to steal my car, right?
  • You’re not married, right? I mean, I don’t want to get in trouble or anything.
  • You won’t just take advantage of me, right?
  • You’re single, right? No, just making sure.
  • You’re not just looking for a temporary distraction, are you?
  • Hey, it’s okay if sex is off the table… for now, right?
  • You’re not just after casual sex, correct?

When you ask these questions, make sure she knows you’re kind of joking but still serious enough to make an impact. It’s all about the delivery.

For example, imagine if you shared a humorous, exaggerated story about how girls are only interested in you for your body. You just want a girlfriend, but they keep contacting you for booty calls.

Again, do these sparingly, or just once even. If she laughs the first time, yeah, maybe a second time a little later would do.

“You’re not just looking for a fuck buddy, right? I mean all I want is genuine connection with women.”

Sex Questions

Around 3, 4, or more hours into the date, depending on how things are going, you and her may find yourselves getting more flirty, and things might start heating up.

There could be hand-holding, kissing, or even making out from time to time.

Now, at this point, you should have moved your date to somewhere more private. Here are some questions you can ask her to possibly get her more in the mood to sleep with you.

Remember, only ask these when you want to pull the trigger right there. If you’re not anywhere near a place where you can get her in bed, try to avoid asking.

When you ask these questions, you want her to be ready to jump in bed with you.

  • What’s your favorite part about your body?
  • Do you like it rough or sensual?
  • Do you prefer to give or receive?
  • Do you have sex toys?
  • What do you think about spanking?
  • What’s your favorite type of foreplay?
  • Do you like getting choked?
  • Do you like your hair getting pulled?
  • Which celebrity do you secretly fantasize about?
  • What’s the naughtiest thing you’ve ever done?
  • Do you watch porn?
  • Where’s the weirdest place you’ve done it?
  • How often do you masturbate?
  • Have you tried it in the car before?

Remember, only ask these questions when sex is on the table. During first dates, it can happen or may not, so only use this when it’s about to.

Run-of-the-Mill Questions

While run-of-the-mill questions may seem ordinary, they can still be effective for getting to know her better and keeping the conversation flowing.

These questions can include asking about her favorite music, movies, or travel experiences.

While these questions may not be as deep or intimate as others, they can still provide valuable insight into her personality and interests.

However, these are the questions you might turn to when you’re running out of other topics to ask. They serve as your backup plan.

Don’t make these questions the focus, but also don’t just ask generic questions.

Find more engaging and creative ways to ask about her favorite food or hobbies to keep the conversation interesting and flowing smoothly.

  • Have you seen any good movies or TV shows recently?
  • Who’s your celebrity crush?
  • Do you have any hobbies you enjoy?
  • Do you have any favorite local restaurants or cafes?
  • Are you more of a beach person or a mountain person?
Try It Now

Preparing for the first date is fun. Thinking of fun, flirty first date questions to ask women is a good practice to have. But what if you get stood up? What to do when women don’t show up on the date.


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