30 Flirty Questions to Ask a Girl

Maria Montgomery

9-12 minutes

If you have a crush on someone, or simply met someone whom you feel attracted to you need to flirt
with them. Flirting is a lot about teasing, challenging and asking questions. It’s playful, yet with an
undertone of something else. To flirt is actually an art in and of itself; just as any kind of communication
is. If you want to get good at it, you have to practice. It helps to have some ideas about what to say and
do though.

Below you will find 30 flirtatious questions. Of course they are only flirtatious if you say them at the right
time, in the right context and using the right intentions behind your words though. You know this clip of
Meryl Streep on Ellen DeGeneres’ show where she reads the same line as a sulky teenager, as a
seductress and so forth? That’s a great example of intention – the meaning behind the words. If you
sound like a robot asking questions you won’t come across as flirtatious. Flirting is a lot about talking
about things you aren’t talking about. Innuendo.

1. When was the first time you fell in love?

If you are above the age of 25 this is a pretty safe question, meaning they likely got over the person a
long time ago and it’s now a sweet or funny memory, even if it was embarrassing or heartbreaking at
the time. It’s, of course also a way to make them speak of and think of love.

2. What do you desire/dream of in the different areas of your life?

 Getting a person to speak of their
dreams and desires usually fire them up and open them up to you.

3. What do you think is one thing all men should do when dating?
 Now this will get any woman to talk
like there’s no tomorrow as chances are she’s had one or two experiences where men did the polar
opposite to what she expected and desired. And it will give you a clue as to what you can do if you want
to impress her in the future. Actually, knowing what someone appreciates in a relationship is crucial to
making it work.

4. What makes you feel safe?

 Such a simple question, but it will
make a woman adore you, because it will make her think you want her to feel safe.

5. So these days we all text each other right and I’ve found in the past I tend to flirt a lot over text. Do
you think it’s a good way of flirting, or do you prefer if men call you?

Again, this will help you know what to do in the future. Chances are she will prefer texts at some point
and calls at another.

6. What makes you feel loved?

 Here’s another question that will flatter her as it will make
her think you care about what makes her feel loved. Hopefully you do care as well.

7. What do you find attractive in a man?

Making her think about attraction definitively helps as it puts her in a certain frame of mind where she’s
more open to it.

8. Have you ever been on a date that totally blew your mind? Like one of those movie moments?
 If she hasn’t, then ask her what she
thinks would be an incredible date. Again, this will help you when you plan dates in the future.

9. Tell me what you think about love?

If you are asking her about love or her love life, it will alert her to the fact that you’re interested in her.
Most men who try to find out if you’re single, or if you’re interested in them will ask questions about
your love life in one way or another.

10. If we had a genie here with us tonight that’d grant all our wishes, how do you think our lives
would look different in the morning?

This is great for getting a conversation going that can be both fun and flirtatious, as well as deep. You
can talk about what would change on a surface level, as well as what would change on a deeper level in
your lives. And it’s the kind of thing you can play around with for a while – from you know, what your
new palaces will look like, to how many servants you will have to pour your coffee in the morning; one
to pour the coffee, one for the sugar and one for the milk. In other words: you can joke around.

11. If you imagine we had a jet that we could use to go anywhere tonight, where would we go?
 This is also very playful and can lead
to some flirtatious scenarios.

12. Where’s your favorite place to get a butterfly kiss?

Whilst someone can answer their forehead, you can also take this discussion…elsewhere.

13. What do you think is the number one blunder men make when flirting with or hitting on women?
This will definitively tell you what not to do. It will also make her happy as she thinks you’re trying to
avoid making those mistakes with her. There’s honestly nothing better than a man asking what you like,
what you care about, etc. and who respects that. Whilst we love a man who takes the initiative, it helps
if he found out enough about us to know what he’s doing when taking the initiative to do something!
And that he cared enough to listen to us in the first place.

14. Have you ever done something crazy you’d never do again?
 Maybe it’s not directly flirtatious but
it will get you thinking about somewhat exciting and funny things. Of course, depending on how
they/you present your craziness.

15. Do you feel like you’ve discovered your true self?

Now this is deep. Deep, deep, deep.

Research, however, shows that intimacy fosters attraction as you feel more closely connected to one
another. Normally attraction builds over time as you get to know each other better. If you speed up the
getting to know each other process and look each other in the eye…magic happens faster!

16. If you could do anything for someone in your life right now, what would it be and who would it be
for?
Again it’s going a bit deeper and showing how caring they are when it comes to the people in their life.

17. What kind of parties do you like?

Parties are where you often flirt with

people after all, isn’t it?

18. What’s more romantic, or sexy: cooking for someone or dancing with someone?

A flirtatious question in nature that will also reveal if they have two left feet or not. Could give you an
idea as to what to do on future dates (salsa and swing dancing parties, or not). Then again, some
people’s idea of dancing isn’t necessarily everyone else’s…I dated one guy who was certain he could
dance, though he mainly looked like a mad monkey who’d escaped the jungle. Some people find food
very romantic and sensual as well, which you can also play around with on future dates. Of course, them
talking about romance will help with the flirtatious mood in the moment too!

19. If we only had twenty-four hours together, what do you think we’d do?

Remember the movie Before Sunrise? There’s a lot of things people would do and say if they thought
they’d only have 24 hours together, that they’d otherwise never dare do or say. Can be an excellent
concept for a date as well – go on a 24 hour date and do all those things.

20. What was your first kiss like?

 Don’t ask this question if you’re
fifteen and think she’s never kissed someone…but if you’re older this is a fun way of talking about past
blunders and glories in the kissing department!

21. What was the most perfect moment ever when you received a kiss?

Same reasons as the question above.

22. I really love your dress/top/skirt; it makes you look lovely. Do you think clothes alters the way we
perceive people when we first meet them? Or are they just superficial?
 Here’s an opportunity to get a
compliment in there!

23.  So far, what are three words you think describe me?

Here you can then move onto describing her – which will make her blush as she will feel flattered by the
attention. Any woman you flirt with wants you to pay attention to her; she’s not just one of thousands of
pretty girls, she’s the one you chose to focus on.

24. After a long day when you get home, what’s the best way to make you relax? Should I make you
tea, hug you, pour you a bath, serve a glass of wine, have dinner ready? What really works?
 She will swoon as she will believe
you are that caring guy…so you better be!

25. Me and my friends once made this silly bet that we’d x, y, z. Have you ever had some crazy bet
with someone?

This obviously only works if you’ve made a bet with a friend, or a group of friends. The cool thing is that
you can then move onto making a bet together. Challenge each other. Play around. Get some
excitement going.

26. If you had 24 hours left to live, what’s the one thing you’d do that you wouldn’t dare do today?

Trying to build up sexual tension with your crush? We’ve all been there. Try these flirty questions to
ask a girl you like, and see the difference.

If you’re trying to intensify the sexual energy between you and the girl you’re crushing on, then you can
ask flirty questions to spark a conversation and break the tension. Who doesn’t like being asked a
naughty question? They’re so fun to answer. And if she’s already interested in you, then she’ll have no
hesitation answering them.

Flirty questions to ask a girl you like

When it’s late at night and you know she’s in bed, sending her one of these questions in a text will wake
her up. So, have fun with it and see where each question will take you. Just remember, if she’s not
responding positively, or if things become a little awkward, then tone it down a bit and ask her more
subtle ones.
Make sure you answer these questions too! This isn’t an interview. If you participate, it’ll make it more
exciting and enjoyable – plus, she’ll also be able to learn things about you as well.

#1 What did you think when you first saw me? This will clear up any misunderstandings you may have
had. If you’re not sure if she is into you, ask this question. You may not like what she says, but you’ll at
least get an answer. If she doesn’t respond… well… now you know.

#2 Have you ever been caught masturbating? This is one of the most revealing flirty questions to ask a
girl you like. Well, if she’s interested in you too, that is! It is a great way to share some embarrassing
stories and have a good laugh. You’ll be able to break the ice a bit and get into more flirty questions.
[Read: 15 really obvious flirting signs between a guy and a girl]

#3 When was the first time you had a wet dream? Maybe she remembers the first time she had a wet
dream. I don’t remember mine, but she might be a really sexual girl. She may be nervous to answer this
question, so if you answer first, you’ll break down the barrier.

#4 What’s your favorite place to be kissed? You don’t have to re-enact her answer, but it’s not a bad
idea keeping it in mind.

#5 What’s your biggest turn-on? This is a great question to see what she’s into and to see if you two are
sexually compatible. Whatever she says, remember her answer. This will come in handy for later, trust
me. Plus, if she notices that you were listening, you’ll score even more brownie points. [Read: 36 racy,
random funny questions for flirty guys and girls]

#6 Would you rather be considered sexy or smart? What matters to her – looks or intelligence? You
may not think this is important, but you’ll see how she sees herself and what she values in life.

#7 What’s your biggest turn-off? Just like the “what turns you on” question, this is one of those flirty
questions to ask a girl you like where the answer plays a big part. There’s nothing worse than when I tell
a guy what I don’t like and then he goes and does it. Was he not listening? Apparently. So, if you’re
going to have selective hearing, at least pay attention to this answer.

#8 If you could hook up with any celebrity, who would it be? This is just a fun question that all girls love
answering, and it gets the imagination going.

#9 What do you wear to bed? Maybe she sleeps nude, well, you’ll never know until you ask. Plus, it’ll
probably leave you with a nice image in your mind if she says that she sleeps naked or only with
underwear on. [Read: 20 dirty questions to ask a girl and leave her wet]

#10 Who do you think should make the first move: the girl or the guy? Does she like being in control or
does she like the man to take the reigns? Maybe she likes to take charge, and in that case, you have the
easy road.

#11 Tell me three words that describe yourself? This is a great way to see who they think they are, and
what they consider their important qualities. Not only that, you’ll be able to see whether they describe
personality traits or physical characteristics.

#12 Have you ever had a friend*s*-with-benefits? Find out if she’s engaged in any open relationships.
You can also see if she’s remained friends with her friends-with-benefits. This is a good way to see how
she handles relationships that were just based on friendships – and sex. [Read: How to make a girl want
you and desire you sexually]

#13 Do you like dirty talk? How do you know if you can talk dirty to her if you don’t ask? This is a great
question to see what her boundaries are in the bedroom.

#14 Where’s the most public place you’ve had sex? Perhaps she likes having sex in public, or maybe
she’s more of a private person. It’s a good way to see how kinky she is and if she’s willing to try it out.
[Read: 20 make-or-break freaky questions to ask a girl]

#15 Have you ever used a sex toy? If she has, then she won’t hesitate to bring it into the bedroom. If
you’ve used sex toys and she hasn’t, this would be a good opportunity to ask her if she’s curious about
trying. If she is, well, now you’ll be able to bring it into the bedroom.

#16 Do you like cuddling when you’re in bed? It’s always good to know if you’ll be having a numb arm
or not. If you like cuddling and they like cuddling – great! [Read: How to cuddle with a girl so it leads to
sex every single time]

#17 Have you ever kissed a girl before? Well… has she? If so, ask her if she enjoyed it and would do it
again. Maybe she’s interested in exploring her sexuality with you.

#18 Boxers or briefs? I know this may seem like a silly question, but why not know what turns her
on? Flirty questions like this will help her envision you without your clothes on.

#19 What’s your ideal romantic date? Pay close attention to this answer and see what she’s really
looking for. Maybe she’ll say skydiving or snorkeling, but maybe she’ll say a picnic along the riverside.
Whatever the answer, you’ll be able to see what she’s into and what she’s looking for in a relationship.

#20 What do you think is my best feature? See what turns her on about you. Maybe it’s your smile or
your sense of humor that lures her. [Read: 20 funny questions to ask a girl and leave her ROFL]

#21 Have you ever had a dirty dream about me? Yessss, this is a great question to ask. If she says yes,
then ask her what the dream was about. See if maybe you can re-enact it for her. You know, to make
her dreams come true.

#22 What’s your favorite part of a man’s body? As a woman, I know that all women have an answer to
this question. We’ve thought long and hard about this one. Strong arms, firm jawline? She’ll have a
couple of body parts on her list. [Read: 11 moves to seduce any girl and get her in bed]

#23 Would you ever have a sugar daddy? Is she into having a guy buy expensive things for her and take
her out to fancy restaurants in exchange for sex? It’s a good way to see what she values in life and how
far she’s willing to go for material possessions.

#24 Have you ever had an orgasm? Now, this is a crucial question. Maybe she’s never had an orgasm. If
not, well, it’s your job to give her a first orgasm. If she has, then ask her what makes her orgasm.

#25 Do you want me to kiss you? If she’s interested in you, she’ll say yes. I mean, this flirty question to
ask a girl is basically the golden ticket – so use it when the moment is right.
 Again, this is exciting as it’s
challenging. And adrenaline makes us fall in love faster, as does revealing intimate things about our life.

27. Do you believe in love at first sight?

Of course there’s attraction at first sight, but can you truly know if you can love someone after just
seeing them for a few seconds? Or is that just attraction that could develop into love and a caring
relationship (three very different things).

28. Do you have any dreams you dream a lot at night?

 Again, intimate.

29. Do you have a dream about something you’d love to do in life that you haven’t revealed to
anyone?

This is the kind of discussion you have at midnight when the lights are dim and you suddenly reveal all
those things you thought you never would…

30. What do you think are three ingredients that would keep a relationship exciting through the
years?

Deep, hot…this question could lead

anywhere…

BONUS: If you could be anywhere with me right now, where would it be?

Having the other person use their imagination to come up with a scenario of what you could be doing
together can be a lot of fun. It also allows you to explore scenarios that can be extremely romantic or
sexy.

Remember with all these questions that it’s not just about the questions – it’s about how playful, teasing
and challenging you put them, as well as how you answer them yourself. If you are all serious and stony
in your replies, this won’t be a flirtatious chat. You have to be honest, provocative, humorous and playful
all at the same time.