Flirty First Date Questions

Flirty First Date Questions

Nothing beats a cheeky flirt with a cute guy, am I right? Whether you’re just getting to know him, or want to really find out more about him and how much he’s interested in you – asking some flirty questions to a guy is a great way to do so. 

If the art of flirting doesn’t come naturally to you then not to worry at all as we have compiled the ultimate list of great questions that are sure to grab the attention of any guy + an infographic (be sure to read to the end!) We have it all from funny questions that’ll break the ice and get you both laughing, to deep questions that let you take the conversation to the next level. 

Flirty Questions to Ask a Guy 

Here are some of the easiest flirty questions to ask a guy and slip into conversation that can create a cheeky spark between you both whilst allowing you to get to know them better. They even give the opportunity to slip in a few nice compliments in too, which is always great plus!  

What do you look for in a partner?

This is a direct indication of whether there is a romantic interest from the offset. 

What’s your favourite thing to do on a date?

Grab dinner or maybe something more activity-based…

How often do you workout?

Making him feel good about his appearance is always a great affirmation to give him. 

How are you still single?

A nice boost to his self-asteem as well as a chance to see any red flags that you need to be aware of…

What are your biggest passions right now?

Get to know a bit more about him, his hobbies and biggest interests at the moment etc. 

Describe yourself in 3 words

It’s good to see how he views himself and the words he’d use to describe himself. 

Describe me in 3 words 

Also good to see how he views you and the words he’d choose to describe you. 

What makes you laugh?

Always good to get an insight into his sense of humor and how to get him to chuckle. 

Are you drawn to brains or beauty?

A balance of both is a totally acceptable answer. 

What do your weekends look like, and how do I fit into them?

This question allows you to get to know how he likes to spend his downtime, as well as giving you both the chance to envision how to spend that downtime together as a potential future couple. 

Do you prefer staying in or going out?

Do your social lives match?

What do you think is your greatest achievement?

There’s nothing sexier than hearing a man speak passionately and proudly about what he has achieved in life so far. 

What do you think your best feature is?

This is a great window to open for a stream of ongoing compliments.

What do you think my best feature is? 

And carry the stream of compliments going…

Have you ever made a really romantic gesture?

Find out how romantic he is, whether it suits your romance levels or not!

What does your future look like?

Is he a “take one day at a time” type of guy, or an avid planner? How do you fit into his plans?

What’s your favourite thing to do?

Maybe you could do it together for your next date!

What makes you smile?

Making him smile is a great flirting technique. 

If you were an emoji, which one would you be?

Kissy, smiley, or winky face? Or is it something else?

Do you prefer being the little or big spoon?

Is he even a cuddler, and if he is, what kind of cuddler is he?

If we went on a date, what would it look like?

Sometimes it’s best to just be direct and gage his response. 

Funny Questions to Ask a Guy 

Making each other laugh is an important part of a healthy and satisfying relationship. Moreover, according to research, finding a partner with a similar sense of humour highly improves your chances of building a long-lasting strong relationship. So, what better way to get an idea of his sense of humour than by asking these totally funny, yet still flirty, questions to him! 

Which actor would play you in a movie about your life?

Is he a Hollywood stud kind of guy, or your favourite side-kick character?

Do you flip your pillow to the cold side?

A great chance to find out more about his other sleeping habits!

Are you ticklish?

Where are his main weak spots… It’s also a great chance to test it out and see if he’s telling the truth!

What gets you flustered?

Find out what makes him blush – an embarrassing situation or more like a cheeky flirt?

Who’s your celebrity crush?

He must have at least one, if not more…

What are your favourite pizza toppings?

This can actually tell you a lot about a person, are they pretty basic or super adventurous with their food and flavours. 

What 3 items would you take to a deserted island?

Is he a luxury kind of guy or a “survival of the fittest” type?

What makes you squirm the most?

An embarrassing memory or maybe an awkward encounter with someone you’d rather avoid…

Are you a dog or a cat kind of guy?

And does this suit your future pet plans together? 

Deep Questions to Ask a Guy 

What’s your biggest fear?

It can be a real turn on to see a guy’s more vulnerable side in between some flirty conversations. 

Who was your first love?

This can often leave a lasting impression on a guy and shape his attitude towards love and dating

What do you like most about dating?

The deep companionship or just the physical side of things…

How do you define love?

Is it something he even wants right now or is he after something a bit more casual?

Who do you most admire?

A close friend, family member, or a famous figure?

What does your dream life look like?

Is he after the rich pad with sports cars or a more modest life filled with a big family? 

What drives you in life?

Is he driven by money and success, or by deeper, fulfilling relationships?

How long was your longest relationship for?

Has he ever had a long-term relationship and how did it affect his views on dating?

When was the last time you cried, and why?

Is he able to tap into his emotions easily or is it more challenging for him? 

What do you value most in a relationship?

Particularly his core values, and do they match yours? 

There you have it! flirty (and not so flirty) questions to ask a guy you like on your first date. Hopefully, these will help you break the ice and get to know your man better.