- HUMOR
50 Funny Batman Jokes
At any age, dating can be a daunting thing, and whilst fun if it goes well, even the smartest of us can falter under pressure… And dating is definitely one of the biggest pressure-heavy times of our lives. It’s worth having a collection of questions to hand to get to know a person better, to relax the conversation, and of course to steer things in a way you both want – so you really understand the person you’re dating!
General Flirting
Light hearted fall back stuff, more random fun to spice up the conversations and ensure you’re getting great intel on how your date likes to be and act.
— 15 Flirty Questions to Ask a Girl
What’s the sexiest thing a partner can do for you?
What’s the best way to charm you?
What’s worst flirting you’ve experienced?
Rate my flirting so far out of 10?
How many dates have you been on this year?
How many of those do you wish you could forget?
How high up does this date rank amongst them all?
Do you have any brushes with celebrity when it comes to flirting?
Would you date someone completely opposite to your type, just to see?
If someone was really good looking, but couldn’t make you laugh – would you still be interested?
What’s the worst most cringey flirting you’ve ever tried to do?
Do you think your flirting is always successful?
Do you have a go-to style or method to make someone like you?
How much do you focus on your dates outfit when you meet them?
How many dates do you wait before a kiss?… And more?
Random
Just more fun to break the ice and get to know your date better. There’s nothing like sharing all kinds of information so you really offer yourself up to you them, and them to you.
— 15 Random Flirty Questions to Ask a Girl
Have you ever been with a celebrity?
Who’s your biggest celebrity crush/hall pass?
What’s the worst date you’ve ever been on?
What’s your most embarrassing sex story?
Where’s the most bizarre place you’ve hooked up with someone?
What’s the best chat up line you’ve heard?
Do you prefer guys dressing casual or smart?
Do you prefer dressing casually or getting glammed up?
What are total no-go’s for relationships?
What are your must-have’s for relationships?
Do you like to go to the gym or play any sport?
Would you binge-watch a series with me?
What’s a weird trait that you find attractive about me?
What’s one drink that gets you wild without fail?
What one thing would you change about me if you could?
Love
If love is what you’re after, it’s so helpful to understand the way your date feels about and responds to love. That doesn’t mean you have to be “in love” right away – it’s just good to understand how people work emotionally.
— 20 Flirty Questions to Ask a Girl About Love
What is your love language?
Do you think you can love someone who (only) speaks a different language?
What’s your favourite way to show affection?
What’s the nicest gesture someone has made for you?
Have you ever been in love?
How many times have you been in love?
What is the most romantic thing someone has done for you?
What is the most romantic thing you have done for someone?
What is your ultimate romantic holiday?
What’s your favourite love story, either film or book?
Are you looking for love now?
Do you prefer to make the first move or have them make the first move?
Have you had much luck with dating on apps?
Do you think opposites attract?
What’s more important, a good body or a good mind?
What’s your idea of a perfect date?
Would you rather?
A fun ice breaker; “would you rather’s” get the conversation flowing whilst creating laughable situations. The best part is, it can be passed off as hypothetical or fiction so even difficult questions can be a laugh.
Would you rather go on top or bottom?
Would you rather be a bird or a shark?
Would you rather have a cat or a dog as a pet?
Would you rather be able to fly or breathe underwater?
Would you rather eat sweet or savoury for the rest of your life?
Would you rather marry for love or for money?
Would you rather always be a little too cold or a little too hot?
Would you rather take a road trip or fly somewhere?
Would you rather always be in winter or summer?
Would you rather be a top athlete or a world-famous singer?
Would you rather fight a thousand spider-sized bears, or one bear-sized spider?
Would you rather it was always day, or always night?
Would you rather a day on the sofa together, or a day out and about?
Would you rather die a hero or live long enough to see yourself become a villain?
Would you rather the best night of your life once, or an OK night every night forever?
Entertainment
It’s a need to know, what kind of films and songs they like. How else will you pick “your” song together? Or that film you went to watch that you laugh or cry about together for years to come.
Would you go for a Mr Darcy or a Mr Bingley?
What’s the best gig you’ve been to?
Do you enjoy much theatre?
What’s the most moving scene in a film you’ve watched?
What’s a song that means a lot to you?
What’s the best line you’ve read in a book or poem?
What’s the funniest film you’ve seen?
What TV series are you into at the moment?
Did you ever have a crush on any cartoon characters as a kid?
What song gets you in the mood without fail?
Have you got any tattoos?
Are any of your tattoos in funny or intimate places?
If you were being hunted by the villain from the last film you watched, how screwed are you?
And if you were going to be saved/helped by the hero from the last (different) film you watched, would you survive?
Do you play many video games?
Fun
In a similar vein, just general nonsense will help lighten the mood, whilst getting a taste of what your date is like. Plus having the questions returned means you can present yourself through light hearted questions like the below.
— 16 Flirty Questions to Ask a Girl
Shag, marry, avoid – David Tennant, David Cameron, David Attenborough?
Tell me your favourite rude joke?
If you were an ice lolly what would you be?
What are three things that turn you on?
What are three things that turn you off?
If you could be the opposite sex for a day, what three things would you do first?
Do you have any nicknames?
Have you ever ridden a motorcycle?
Have you ever skydived?
What do you like best about me?
What’s the first thing you would buy if you won the lottery?
What’s the best gift anyone has bought you?
What’s the worst gift anyone has bought you?
What’s the best gift you have bought for someone?
Have you ever stolen anything?
Life
Always worth knowing about their general life if you want to spend more time together, it’s also helpful to identify what to avoid around your date.
Are you an easy sleeper?
What are your pet hates or “icks”?
Do you have any party tricks?
Would you say you’re a good kisser?
Are you ticklish?
Where are your tickle buttons?
Are you a night owl or an early bird?
Big night out or cosy night in?
If you could only drink one think forever, what would you pick?
If you could only have one meal forever, what would you pick?
Do you believe in karma?
What hidden talents do you have?
What job do you wish you could do for a day?
What’s your biggest guilty pleasure?
What’s your spirit animal?
Deep and meaningful.
As the conversation gets more comfortable and you both realise you want to know more, to learn about the nitty-gritty, it’s great to get deep and meaningful. What’s perfect about this is you can really share intimate stories with each other to drive home just how much you want to spend time with them.
Are you close with your family?
What do your siblings tease you about the most?
What’s your best memory as a child?
Did you have any nicknames as a child?
What did you get in trouble for most as a child?
What experiences/views on life from your family do you take with you always?
What habits have you adopted from your parents?
If you could re-experience an hour of your life, when would it be and why?
If you could change an hour of your life, when would it be and why?
Do you ever imagine we have company in the Universe?
What achievement are you most proud of?
Who would you say is your strongest influence/idol?
Have you ever experienced heartbreak?
Tell me something about yourself nobody knows?
Do you have any fears?
Travel
Travel is a brilliant subject, not only for the memories but potential plans for a future together. Present these questions in ways to make your date picture the both of you experiencing great adventures together.
Have you done much travelling before?
Where would you take me if you were to plan a week’s holiday together?
Would you trust me to plan a week’s holiday for us?
Where is your favourite destination to visit?
Where’s on your travel bucket list?
What’s your ideal destination for a weekend break?
City holiday, or countryside?
Camping or Hotel?
Have you ever lived abroad?
Would you like to live abroad?
Would you ever backpack the world?
What’s your favourite cuisine from around the world?
Have you any tattoos from your travels?
Have you ever fell in love with someone while travelling?
Have you lived anywhere abroad?
Hopes & Dreams
A bit like deep and meaningful and travel rolled into one. Get your date picturing special times together, imagining a future of sharing special times.
Are you in your dream job?
What is your dream job?
Where do you see yourself living in five years?
Could you see yourself having children?
If so, just one to spoil them? Or lots for a big family?
Describe your dream house?
What’s your dream car?
Is there a skill or talent you wish you had?
What did you always wish you would achieve?
Are you what you wanted to be when you grew up?
What are you most afraid of missing out on as you get older?
What’s your five year plan in terms of love?
What one thing would you most wish to experience in life?
What famous person would you most like to meet?
What’s the biggest lesson you’ve learnt from your parents?
I'm a 28-year-old writer from Norfolk, England with a penchant for creating content based around lifestyle and culture. I'm a big fan of creating new ways for people to interact so I hope you enjoy these conversation starters.
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