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18 Flirty Questions To Ask A Woman Online & In Person

18 Flirty Questions To Ask A Woman Online & In Person

18 Flirty Questions To Ask A Woman Online & In Person

Changing romantic gears is a process that involves tact and oodles of skill… or plagiarism.

Going from the stranger zone to the romantic zone isn’t an easy transition.

To help you out we’re supplying you with flirty questions to ask a woman either on a dating app or in person.



These questions are designed to signal your interest as well as pique hers.

Without further ado let’s get flirting!

Flirty Questions To Ask A Woman Online

First up, questions that you’ll want to ask online.

Most if not all of these questions are designed to be asked right off the bat.

As soon as you score that match message her one of these bad boys.

Our research shows that 75% of all first messages are nothing more than “hey” or a shallow variation.

You can stick out from the rest of the guys on these apps by writing literally anything else.

However, if you choose to write one of these lines your chances of not only receiving a response but piquing her interest will drastically increase — trust me, I’m a professional dating coach.

1) Get To It

“So tell me, Steph, what do you like to do when you’re not flirting with strangers from Tinder?”

Look, flirting online is a numbers game. It’s true that this message might scare some women away, however it accomplishes a few things.

It’s original, spicy, and asks a question.

It’s daring yet is a great conversation starter because it asks a genuine question. As a flirty opener, it also sets the tone for the flirty conversation to come.



2) The Neg

“Apart from your love for zebra print, tell me something cool about you.”

This is a classic neg.

Let’s imagine for a moment that this is her profile picture.

flirty questions to ask a girl

Let’s also imagine that in four of the following five photos she’s also rocking Zebra print. We’ll also say that she has no written bio.

Coming across a female that basically has the same style photo for her entire photo library along with a blank written bio is fairly common.

In my opinion, you shouldn’t waste too much time with these ladies. Clearly, they haven’t put much time into creating a worthy profile either because they’re not serious about meeting someone on the app or are too socially unaware to realize not doing so makes their profile garbage.

Being that they gave you little to work on, gently make fun of their profile before requesting more information about them.

Chances are she won’t respond. I don’t say this because she doesn’t like your profile or because the opening line is lame, rather regardless of how good your online persona is it’s doubtful, you’ll get a response.

flirty questions to ask a girl

When she inevitably doesn’t respond, keep the joke going by writing, “There’s nothing cool about you? I don’t believe you.”

Only send her a follow-up message 48 hours after having sent the initial message.



3) Sizzle Sizzzzzle

“So what do you do apart from talking with cute guys on Bumble?”

Because that’s what she’s doing.

She’s not here to make friends or pen pals, she’s here to find a man.

And if she isn’t here for those two reasons she either won’t answer or will tell you so.

This is perfect because it’ll allow you to weed out women that aren’t interested in meeting up.

Should she take the bait, she’ll probably comment on her flirting ability. She’ll say something like, “we haven’t even begun to flirt yet” or “I’m such a bad flirt.”

You want to get her talking about flirting and romance without creeping her out or pushing the issue too quickly.

4) A Game Of Push And Pull

“Obviously, you’re beautiful but tell me something your photos don’t portray about you.”

Generally speaking, commenting on a woman’s appearance online is a no-no.

Tons of guys do it and many do so in lascivious ways.

That being said, commenting on her good looks because pulling back and asking her to impress you with her personality is a good call.

It shows that you’re interested in actually getting to know her rather than just getting her into your bed.

5) The Smooth Talker

“Tell me, Allie, what do you do when you’re not busy breaking hearts?”

Assume that she’s a badass and she will respond in kind.



Telling her you think she’s a slayer is basically the same as calling her hot. The only difference is that you’re not being cliche or creepy.

To boot, you’re also asking her about her hobbies. This flirty question is much easier for a woman to respond to than a non-question about her appearance.

6) The Hard Neg

“Your profile tells me so much about you, from your love of selfies to your incomparable use of sepia tone, but I can’t help but think there’s something about you that I still don’t know… want to fill me in?”

If the previous neg was soft, this one’s a bit harder.

This message should only be sent to a woman who has written next to nothing in her bio and whose photos are all basically the same.

7) The Flirty Song Lyric

“Your profile screams “I just took a DNA test, turns out I’m 100% that bitch,” what I wanna know is can I be your man from the Minnesota Vikings?”

Obviously, this line works best if she’s a Lizzo/Vikings fan, but considering the awesome compliment and the popularity of the song, you should be fine.

8) Secrets Secrets

“Hey Becca, tell me a secret.”

Regarding flirty questions to ask a woman online, this one is simple but highly effective.

It slowly but surely begins the process of peeling back her defense.

The best way to become intimate with someone is by opening up. Begin the process with the Tinder first message.

9) To The First Date And Beyond!

“Sam! What’s your ideal first date… I swear to god if you say “x” I’ll marry you right here and now.”

Show her what you’re about.

You’re using dating apps not to collect matches or talk to strangers, but to go on dates.

Make your intentions clear and set the tone with your very first message.

10) Segue Into The First Date ASAP

“What are you thinking of right now? – apart from Nutella milkshakes and how cute my face is.”

This one works both online and in-person.



It also works because it’s odd.

I guarantee no one has ever sent a message like this one.

Some women will enjoy that, others won’t.

You’re taking a chance when you guess she’s into Nutella and your face.

That being said, if you’re not taking chances online you probably aren’t scoring many numbers.

The best thing about this message is that you can swap out milkshakes (for something you see she might be into from her profile) and that it’s easy to transition from this message into asking her on a first date.

If she’s into milkshakes shortly after sending this message use a TDL to ask her to get milkshakes.

11) Get Musical

“Yo Katie… what song always makes you shake your booty on the dancefloor?”

There are a few emotive things you’re touching on here:

— Going out on the town

— Dancing

— Booty

— Music



An opening message that somehow isn’t explicitly sexual that touches on these four things is a winner.

After this, she’ll likely respond with a song she’s super into right now to which you’ll respond with one of your own.

Vibe out to your musical tastes for a while before asking her to a show or a bar with awesome music.

12) Giver Her Options

“Hi Beth, I have three options for you:
Juicy pickup line
The line that’ll immediately make you fall in love
The Office quote”

Women love a flirty interactive opening message.

This isn’t a message you’ll want to send to every woman. Makes sure it’s personalized for each woman you message. Also be mindful that this message may take a second to craft. Only send it to highly desirable women you think get bombarded with messages.

13) You Cheeky Dog

“So why are you so into guys named **your name?”

You sly dog you.

This clearly is an edgy opening line, one that may need to be backed up with some witty conversation.

If she doesn’t quite get the message and responds with “…what?” tell her that for all you know you only swipe right on guys named, “your name” and are a little creeped out by her odd fetish but you’re not one to judge so you’ll give her a chance.

Flirty In-Person Questions To Ask A Woman

If you’re audacious enough you could ask most of the aforementioned questions in person, however, if you’re not so ballsy, here are some other flirty questions that are better suited for in-person flirting.

14) Get Her Talking About Romance

“What type of guys do you normally date?”

Obviously don’t bring this up out of thin air.

When the time is right ask her about her dating life.



This is flirty because it’s edgy. It’s also a question about her romantic life. Ideally, you’d joke around with her and turn the conversation about-face so that you two are now talking about your romantic potential.

Drop this bomb of a question later on during the date, ideally after a few drinks have been consumed.

15) Get Real

“Tell me about your worst Tinder date.”

This might be one of my favorite flirty questions to ask a woman in person, but it comes with potential consequences.

What you want to hear is a PG-13 story about a crappy Tinder date.

What you don’t want to hear is how a Tinder date of hers attempted to sexually assault her.

Use tact and make it known that you want to hear a funny date story rather than a terrifying one that will bring up feelings of trauma.

16) Tell It Like It Is

“What do you do when you’re not going on dates with strangers?”

Drop this one early on during a date.

This question is flirty because it one, suggests that she does this often, and two, acknowledges the awkwardness of first dates.

17) The Heavy Jest

“How are we going to fall in love, have kids, and summer in Cape Cod if you don’t like “x”?”

After letting it be known that she’s not into something you’re into, fast forward and scare the shit out of her by talking about the future (in a clearly playful and joking manner).

The more outrageous fantasy you create the better.

Talking about a romantic future together will make it easier when it comes to being physically romantic or asking her out on a second date.

18) The Moneymaker

“So should we kiss here or by the car, really I’m fine just about anywhere.”

If you’re cool enough to pull this off and are horrible with delivering a first kiss at the end of the date, consider using this line.

Only use this line if you’re 90% sure she’s down to clown.



You’ll know if she shows you one of these signs.

Most likely she’ll just chuckle and make a joke about your flirty acumen.

What About, Well, Everything Else?

A flirty line or two will help you progress the relationship but copying our lines won’t be enough to find you a girlfriend.

For that, you’ll need a bit more help.

Book a 1-on-1 Zoom session with me or one of my colleagues to learn how we can help you become the man you always wanted to be — or rather the man she always wanted you to be.

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