What are the Key Things to Ask a Woman?

Whether you’re preparing for a first date, exchanging messages on Match, or learning more about a new relationship, questions are everything. A good question can make them more comfortable and encourage them to open up, giving you the information you need.

So, let’s look at some fun, funny, engaging, and thought-provoking questions to ask a girl.

The Art of Conversation with Women

Many men struggle to talk to women, yet mastering the art of conversation is the best way to impress women. It doesn’t matter how well you dress or how good you smell; if she finds it difficult to have a conversation with you, the relationship isn’t going anywhere.

Here are a few ways to master the art of conversing with women:

Essential Questions to Start a Conversation with a Woman

You’ve found a girl who seems to have just what you’re looking for. You want to impress her, grab her attention, and start a conversation. But what do you say? Unfortunately, for many men, the answer is a simple “hi”, occasionally followed by a compliment. But that’s not going to get you anywhere. Instead, try one of the following:

Get Them Talking About Their Pets

Animal lovers like to talk about their pets. If they have multiple pictures with their pets, there is a good chance they fall into this category and will happily gush over their fur babies. Find something personal to say if you can, such as “Is that a [breed of cat/dog]? I love them. They have such a great temperament, don’t they?”. You can also try the following:

• If you could be any animal, which one would you be, and why?
• Are you a cat or dog person?
• What was your first ever pet?
• What pet would you get if you had plenty of time and money to care for it?

Thought-Provoking Icebreakers for Any Occasion

Get her thinking and she might open up, giving you the “in” that you need and ensuring the ice is well and truly smashed to pieces.

Create fun scenarios

• The world is going to end in one hour; how do you spend your last hour?
• You have to listen to one album every day for the rest of your life; which one do you choose?
• If you could live the life of any fictional character, which one would you choose?
• Which fictional universe do you wish was real?
• What would be the title of your autobiography?

Ask about her interests

• What is your favorite thing in the world?
• What common thing that many people own have you never bought and will never buy?
• What is your favorite thing that you own?
• Was there ever a time in your life when you wished you had quit when you were ahead?
• A genie gives you three wishes and they can only be for selfish things, what are you wishing for?
• If you could only watch one show for the rest of your life, which one would you choose?
• If you could go anywhere in the world right now, where would you go?

Strange Questions to Ask a Girl to Get to Know Her Better

Sometimes, the best way to get their attention is to say something a little silly, something that no one else has asked them. These random questions can kick-start the conversation while also making you more memorable.

• If you had to compare yourself to a meal, which one would you be?
• What’s the weirdest thing you have ever overheard?
• What is the ugliest or most useless thing you own?
• If you had to build a house out of food, what would you use?
• If you could only have one topic of conversation for the rest of your life, which one would you choose?

Best Questions to Build a Romantic Connection

The best questions are ones that encourage her to open up. They skip the mundane and get down to the things that matter. These deep questions are best reserved for when you’ve had a few dates, as you can’t expect her to be open and vulnerable when you’ve only just met. They are also good questions to ask your girlfriend when you feel like you need to know more about her:

• What is your biggest fear?
• Who knows you best, and is there anything you would never tell them?
• What is your best memory from childhood?
• How do you destress and cheer yourself up when you’re having a bad day?
• Have you ever thought about starting a family?
• Is there any person in your family who you wished you were closer to?
• Do you have a bucket list?
• What do you think is your best quality?
• What experience from your childhood do you wish you could relive?
• Do you think that money can buy happiness?
• What is the proudest moment in your life?
• Do you have any regrets?
• If you had to write an autobiography covering a single year of your life, which year would you choose?

Fun and Creative Things to Ask a Woman

Fun questions and funny questions are ones where you show more of your silly side and let them do the same. They’re good for most occasions and can get the ball rolling in a conversation, letting you slip into more serious questions further down the line:

• What are your thoughts on pineapple and pizza?
• Which emoji best describes you?
• Would you survive a zombie apocalypse?
• What’s the strangest thing you own?
• What’s the strangest app on your phone?
• What would be your job description if you worked at a circus?
• Do you believe in aliens?
• Do you believe in ghosts?
• Would you rather have a horn on your forehead or a tail growing out of your back?
• If your pet made a documentary about you, what would they show?
• You lose the ability to talk and can only make animal noises. Which animal do you want to sound like?

Questions to Ask a Woman Over Text

Most of the questions here will work in person and over text. The most important consideration when asking a girl text questions is to keep them short and sweet. They also need to be interesting enough for the woman not to groan when she sees it. You want her attention. You don’t want to bore her.

• What piece of advice would you give your younger self?
• What’s your favorite all-time movie?
• What was the last concert you went to?
• What’s the best gift you’ve ever received?
• What’s the best gift you’ve ever given?
• What one word describes you best?
• What GIF best describes your life right now?

Curious and Uncommon Questions for Unique Discussions

It’s time to think outside of the box and start some unique conversations. Assuming you’re both interested and willing, these topics will let you get creative. They can teach you a lot about her without asking any personal questions that might make her feel uncomfortable.

• Have you ever seen a ghost?
• Do you think that aliens have visited us?
• Do you believe in any conspiracy theories (if not, ask, “What conspiracy theory do you think is most likely to be true?”)
• If you win $100 million in the lottery tomorrow, how will you spend it?
• What story from your life would work best as a stand-up routine?

Personal Growth and Career Questions

If she is career-oriented or just focused on personal development, you could win her attention and respect by asking questions about her work, studies, and ambitions:

• If you could click your fingers and instantly master any skill, what would it be?
• What is your dream job?
• If you could live your life again, would you change your studies and try for a different career?
• If someone gives you $1 million to start a new business, what kind of business would it be?
• If you won $10 million tomorrow, would you quit your job?
• What language would you most like to learn?
• What happens in your everyday life that people would be surprised to learn?
• If money was no object, which job would you most like to do?

Tips for Active Listening and Responding Appropriately

Asking the right questions is just the first step. You need to back up those questions by actively listening to their reply and engaging with them. Ask some follow-up questions if you can and offer your own opinions. Don’t simply skip from one question to another. You’re not interviewing her; you’re trying to have a meaningful conversation.

Here are some other tips to help you:

• Limit Distractions: Stop glancing at your phone or passersby. Focus your attention on the woman you’re with and actually listen to what she’s saying. If you want to have a meaningful and personal conversation, consider doing it somewhere quieter and more secluded, as she might not feel comfortable opening up where she can be overheard.
• Adopt Open and Receptive Body Language: Don’t fold your arms over your chest and turn away from her. Your body language should be open to show that you are receptive and open to what she has to say.
• Watch for Non-Verbal Cues: Her body language is just as important as yours. Non-verbal cues like turning away from you or breaking eye contact may indicate discomfort, while open postures suggest she is engaged with you and the conversation.
• Stay Within Their Boundaries: You might feel the need to push her on certain topics. You want to learn more about her, after all, and you want her to open up. But you also want her to be comfortable with you, and she won’t feel comfortable if you’re pushing her into talking about something she doesn’t want to talk about. Pay attention to her words and level of comfort and only push her on certain topics if she is clearly ready to talk about them.
• Focus on Her and Not You: The purpose of the conversation is to listen and learn, not to wait until she has finished so that you can speak. It’s okay to plan a response, as that will help the conversation flow, but that shouldn’t be all you’re thinking about.
• Don’t Shy Away From Silence: It’s okay to have breaks in the conversation. Don’t feel like you need to fill every second of silence, as you may come across as anxious and awkward and will just end up filling the silence with meaningless chatter.

Conclusion: Questions to Ask Your Date or Girlfriend

See these questions as the key to unlocking an engaging and insightful conversation. And the more of these conversations that you have, the closer you will get to that person, and the stronger your relationship will be!

So, whether the questions are fun, flirty, cheeky, romantic, silly, or thought-provoking, make sure you’re armed with a few of them during your next date or text exchange.

Key points