10 Flirty Questions To Ask Someone

Get your flirt on with these 10 flirty questions to ask someone, if you dare. These lines are truly awesome, if delivered properly. These 10 flirty questions do not guarantee that you will get the girl of your dreams; heck, they might even get your butt kicked, but always remember: failure is never an option. Here are our favorite flirty questions, ranging from the cheesiest to the tried-and-true.

I’m invisible, but can you see me? How about Friday night? This flirty question is just quirky enough to work. It’s not too forward and it works for both genders. Even a shy person can probably pull this off with aplomb.
May I have directions? (Hopefully they will answer, “To where?”) Answer: To your heart. See flirty question number one as to why this may just work. It is designed to get an actual date out of it, but at the very least it’s a great icebreaker, very sweet and non-threatening. Who knows, the object of your desire may whisk you away on the spot.
What does it feel like to be the most beautiful woman in the room? Now, asking someone this flirty question has been done to death, but it is golden and works every time. Everyone loves compliments, and you can really rock this flirty question if you look straight into your desired one’s eyes, and speak it softly, slowly and sincerely.
That’s a nice dress. Can I talk you out of it? This is one of those flirty questions that may get you into trouble. Again, it’s all in the delivery. If you come off like an animal it will totally flop. Just be careful with this one.
Are you going to kiss me, or do I have to lie to my diary again tonight? This mellow little jewel appeals to the most hard-hearted among us. It’s a nice blend of intimate-meets-purist. Romantic, retro and demure, this is the perfect line for a lady to whisper. Alternatively, a guy could probably work it also.
Are you ever going to consider kissing me? Staying with the kissing theme, this bold, thought-provoking flirty question can lead to all sorts of interesting answers, not to mention situations. This one needs to be asked only in a truly atmospheric place, but is undoubtedly a winner most of the time. Go with your gut and wink or don’t wink.
What is something that you’d never want to be caught doing? We see you shaking your head, but this one has endless possibilities. However, be prepared for the answer. You may not want to know, so if you already have a relationship with someone, understand that this little nugget could make or break your newly-formed bond.
So, what are my chances of engaging in anything more than stimulating conversation? Ok, this one is hardly ever successful, but it usually gets a smile out of someone. Use it as a last resort, and be prepared for the consequences. There is no middle ground with this flirty question. On the upside, however, it’s a “no” or “go.”
Hello, well-formed specimen. Would you care to depart with me towards my residence and observe a documentary on the ontogenesis of another individual just prior to fertilization? Baffle ‘em with bemusement and dazzle ‘em with… well, you know. This hilarious flirty question shows intelligence and a sick sense of humor—always a lethal blend. Irreverent and delightful, this line can get you anywhere you want to go.
Do you know what winks and makes love like a tiger? Then wink. Need we say more? Flirty, aggressive and a proclamation of expertise, this question never fails to get a laugh. It is sexy yet playful and guaranteed to elicit some type of response. Whether she believes you or not, she will wonder. Oh yes, she will wonder.

Whenever you ask someone one of these flirty questions—especially number ten—you should deliver the line with a flirty grin (never a smirk, that’s just sleazy). By the way, don’t forget to wink.

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