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?
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?
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.