300 Questions to Ask a Girl When “WYD” Isn’t Cutting It

 Here’s a fact: coming up with interesting questions to ask a girl can be scary. Approaching one you do not know can honestly feel like approaching a bear in the wild. It would make anyone think twice.

But here’s the thing, talking to girls doesn’t have to feel like pulling out your teeth. The trick isn’t having the smoothest pickup lines for girls; it’s asking the right questions. Whether you’re on a first date, texting late at night, or just trying to know her beyond small talk, if you have the right questions to ask a girl, you stand a better chance of forming a real connection.

This guide gives you 300 questions to ask a girl, broken down into categories so you’ll never run out of things to say. From funny icebreakers to flirty lines, pick the vibe you want, and let the conversation flow.

Best Questions to Ask a Girl

Not sure where to start? These best questions to ask a girl are the go-to classics. The questions are fun, thoughtful, and guaranteed to get more than a one-word answer. Perfect for keeping things light but meaningful.

• What’s your favourite book, show, or movie?

• What never fails to make you smile?

• What were you like as a kid?

• What month of the year is your favourite, and why? 

• What’s the best trip you’ve ever been on?

• What’s your favourite thing to do on a lazy weekend?

• What’s one hobby you could never give up?

• What’s something you’re really proud of?

• If you could live anywhere in the world, where would it be?

• What’s your go-to comfort food?

• Who was your childhood celebrity crush?

• Who knows you best?

• Where did you grow up?

• Where is your happy place?

• Have you ever been in love?

• Are there any friends you’ve lost touch with? Do you want to reconnect?

• What’s a weird or funny talent you have?

• If you had to choose one meal to eat right now, what would you pick?

• At a party, are you more likely to be on the dancefloor, drinking and playing games, or somewhere else?

• How do you think your friends would describe you?

• What’s the most spontaneous thing you’ve ever done?

• What’s your current hyperfixation or guilty pleasure?

• What’s the last thing that made you laugh so hard your belly cramped and you cried?

• What’s something you’ve always wanted to learn but never tried?

• What’s on your bucket list this year?

• What’s a goal you’re currently working toward?

• Do you prefer sunrise or sunset?

• Do you believe in love at first sight or slow burns?

• What helps you reconnect to yourself when you feel lost or disconnected?

• What’s the best compliment you’ve ever received?

Flirty Questions to Ask a Girl

Want to turn up the chemistry? These flirty questions to ask a girl move from light and playful to a little risqué, perfect for when you want her to know you’re interested without going too far too fast. Start with the mild ones, and if the vibe feels right, work your way up to the spicier side.

• What’s your idea of a perfect date?

• What was the first thing that caught your eye when you saw me?

Flirting can be as simple as making plans for the next hangout.

• What would you like to do this weekend?

• Is it okay if I want to kiss you right now?

• When can I see you again?

Everyone gives and receives affection differently.

• What’s your love language?

• Do you like it when someone makes the first move, or would you rather hold onto that honour?

• What kind of compliments make you blush the most?

• What’s your biggest turn-on that’s not physical?

• Who’s your celebrity crush, and do I stand a chance against them?

• Do you think opposites attract, or do you prefer someone just like you?

When you’re curious about chemistry on dates, these can keep the energy flowing.

• What’s the quickest way to make you smile on a date?

• How do you flirt with someone you like?

• Have you ever had a crush on someone you shouldn’t have?

Now we’re getting into the cheekier territory

• Do you enjoy sexting?

• What clothing item makes you feel sexy?

• What is your favourite sexual fantasy?

• What’s the most unhinged thing you have ever done to get someone’s attention?

• What’s a random thing you secretly find hot?

These next ones dig into flirting styles and desires

• What’s your go-to move when you’re trying to impress someone you like?

• What’s the wildest place you’ve ever wanted to hook up?

• What’s your favourite place to be kissed?

• Have you ever stumbled on your words while trying to flirt?

• Do you like a little dirty talk, or do you prefer keeping things sweet?

Dreams, fantasies, and playful what-ifs can really turn up the heat.

• Have you ever had a dream about someone that left you flustered the next day?

• What’s one thing you’ve always wanted to try in bed but haven’t yet?

• Have you ever considered going to a nudist beach?

These last few are bold; save them for when the chemistry is undeniable.

• Would you wear lingerie that I picked for you?

• Would a threesome with me interest you?

• What’s your go-to sex toy?