Flirty Questions to Ask a Girl to Get Her to Smiling, Laughing, and Interested

Adam Cohen
Online Dating Adviser
6 min read3 days ago


Scientists proved that making a woman laugh is the most effective flirting tactic for men interested in casual sex and long-term relationships. So to improve your chances of charming a lady, let’s go over the flirty topics to talk about with a girl over text and in real life.

Flirty Questions to Ask Your Crush

It turns out women are rarely as interested as men believe them to be, despite their best attempts at seducing the opposite sex. So if you’re tired of being ignored or brushed off, upping your flirting moves can be a game changer. To help you out, I’ve compiled a list of the flirty questions to ask a girl over text you can use on social media, instant messengers, or dating sites like One-NightStand or WannaHookUp. All you need to do is pick the appropriate context and approach and tailor the examples I provide to the woman you’re flirting with.

Flirty Conversation Starters

If you have trouble starting conversations over text or in person, try these flirty icebreaker questions that work for any situation and any girl:

  • What’s coming up that you’re looking forward to?
  • It can be a movie premiere, a festival, or a vacation, and it is sure to get the girl excited to share with you.
  • What’s your latest adventure?
  • This question is open to interpretation, so the girl can tell you about her quest for a dream job, vacation, or shopping misadventure.
  • As a kid, what did you want to do when you grew up?
  • Most girls are happy to remember childhood and share their ambitious or silly dreams, and you can keep the conversation going with additional questions.
  • All of the above also work as flirty conversation starters for texting and will likely keep you chatting for a few hours. Besides, they also work as flirty questions to ask an older woman, as they are neutral and engaging enough to be universal.

Flirty Truth or Dare Questions over Text

If you decide to spice things up with a classic game of truth-or-dare over text, and the woman chooses truth, here are some flirty questions to ask a girl to keep her talking:

  • If you were a guy, which celebrity would you want to date?
  • Have you ever gone a whole day without wearing underwear?
  • What is the most embarrassing thing you’ve done?
  • Have you ever gone skinny dipping?
  • What’s the silliest thing you did on a dare?
  • If you had 24 hours to live, which celebrity crush would you want to kiss?
  • How far would you go with someone that you just met?
  • What’s your favorite thing about being in a relationship?
  • If I was food, what would I be, and how would you eat me?
  • What question are you hoping I won’t ask?

Remember to adjust the tone of your questions to your relationship. For example, if the girl isn’t comfortable with explicit topics for now, stick to more innocent ideas from my list. And while you can also try flirty dares over text, reserve them for ladies you know well.

Flirty Would You Rather Questions

If you’re all out of icebreakers and the silence is getting awkward, why not spice things up with a flirty version of the “Would you rather” game? Below, you’ll find my favorite playful and flirty first date questions:

  • Would you rather go dancing or singing karaoke?
  • Would you rather spend all day or all night together?
  • Would you rather have a cat or a dog for a spirit animal?
  • Would you rather your boyfriend be a night owl or an early bird?
  • Would you rather have dinner or breakfast with me?
  • Would you rather have a midnight snack or breakfast in bed?
  • Would you rather have sex without love or love without sex?
  • Would you rather have your dream partner or dream job?
  • Would you rather fall in love at first sight or gradually over months of dating?
  • Would you rather date someone who had zero partners before you or someone who has had lots of partners?

The best thing about this game is that you can always come up with a flirty or funny answer, break the ice, and get to know each other better as you dive deeper into each response.

Flirty Questions to Ask Your Girlfriend

Singles aren’t the only ones to make use of flirting, as couples can use the same love language to emphasize and enhance intimacy in a long-term relationship. If you can’t think of a romantic thing to say, these flirty questions to ask your girlfriend should provide some inspiration:

  • Have I told you today how amazing you are?
  • What’s behind that smile of yours?
  • Shall we fulfill your craziest date idea?
  • What can I do to become your dream guy?
  • Do you want me to be your last first kiss?
  • You make me smile. Can I return the favor?
  • What would make this the perfect day for you?

Of course, if you’re in a relationship, you should know your partner well enough to come up with more personal questions and quips that will make them smile or laugh, but these examples can work if you’re out of ideas.

Flirty Questions to Ask a Girl to Make Her Laugh

If your perfect date is the one where you keep laughing and smiling at each other, you’re on the right track, as it’s the most likely to keep the lady interested. And if you’re out of jokes, here are some very funny flirty questions to ask a girl to get her giggling and smiling:

  • Has anyone ever told you that you look like [celebrity]?
  • What’s the worst thing about being a girl?
  • How does it feel to be on a date with a nerd/workaholic/etc.?
  • So, how are you dealing with your social media addiction?
  • What was your worst date? Does this one make it to the top-5?
  • On a scale of one to ten, how likely am I to get a second date?
  • Do you say that to all the guys you go out with?
  • Want me to tell you about my hidden talents?

Questions to make the girl laugh should crop up naturally throughout your conversation, and even the cheesiest pickup line can work in your favor if you use it at the right time. I suggest you keep a couple of these at the ready and look for opportunities to squeeze them in.

Expert’s Opinion

“After years of researching online dating, I still can’t get over the weird and lazy conversation starters some people use. While there’s nothing wrong with deep questions, most people feel awkward disclosing their biggest fear or dirtiest sex fantasy to a stranger in their very first message.

So instead of resorting to stock icebreakers or ready-made messages dating sites provide, I recommend you show your genuine interest and personality. And relying on science doesn’t hurt, either. For instance, the best pick-up line for men should include the word “beautiful,” while ladies should definitely use “nice,” “handsome,” or “great.” These words increase the likelihood of getting a response on sites like OneNightFriend or AdultFriendFinder. And once the conversation picks up, try some of the questions from this post, but remember to customize them to your potential match.”


Flirting isn’t an innate talent; rather, it’s a skill you can develop the more you practice. So be brave and experiment with the examples I shared and build your own unique flirting style. In time, you’ll have no trouble coming up with flirty questions and compliments on the fly.


How To Reply To “What’s Up?” In A Flirty Way?

“My heart rate” or “My hopes to meet you today” are great ways to compliment the girl. You can also go the funny route and answer with, “Sorry, that’s classified. I can tell you if we meet up,” or “Peer pressure requires me to say ‘not much.”

What Are Some Flirty Icebreaker Questions?

Ideally, you should tailor the icebreaker to your environment. And if you can, squeeze in a compliment and a request for help into your opening line. For example, if you’re in a coffee shop, tell a girl she looks like someone who knows her coffee and ask her to recommend a blend.

Do Flirty Conversation Starters For Texting Work?

They do if you choose the right tone and customize your flirty one-liners to fit the girl you’re talking to. The only way to ruin a flirty icebreaker is by trying to flirt with a woman who is obviously not interested.



Adam Cohen
Online Dating Adviser

Editor on OneBeautifulBride, writer, travel lover. I create the most relevant content that helps single people and couples to build strong relationships.