The Art Of Making Conversation: 5 Insightful Questions That Make A Woman Actually Open Up

Deep conversations don't happen by accident.

Last updated on Nov 24, 2025

Attentive man listening as a woman opens up laughing showing the art of making conversation and questions that help her share more Luiz Woellner Fotografia | Canva
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Striking up a conversation with a woman you're dating can be nerve-racking. While small talk can be fun, it's important to figure out exactly what to talk about so you can have deep and meaningful conversations as well.

Dating and forming romantic relationships can be a difficult thing to navigate because it involves both parties opening up to one another and sharing their more vulnerable side. You can learn a lot about a person when you let your guard down and also provide them with a safe space to do the same.

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Connecting with a woman is important because when dating, you want to get to know them and see if your values and interests align. There can be a lot of awkward silences in the conversation as well, so how do you push through and make it an engaging conversation? You have to bring up topics that allow your partner to express themselves, open up, and then let the conversation flow. 

Here are 5 insightful questions that make a woman actually open up:

1. 'If you could travel anywhere in the world, where would you go?'

You can learn a lot about someone by asking them where they want to travel. Ideally, you want a partner you can go on adventures and explore the world with. You can gauge how adventurous they are based on where they would go and why they would go there.

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They might say they want to go zip-lining in Hawaii or they want to visit their family in Tennessee. By figuring out where they want to be most in the world, you can envision if this is a trip you could see yourself accompanying them on in the future.

By asking this, it helps make her feel more comfortable in conversation because she would be thinking about a place that she would be happy to visit. When she is feeling uplifted by this question, that positive energy will bleed into the conversation and could get her to feel more comfortable going forward.

Also, this question really keeps the conversation going because you both can talk about where you have traveled to in the past and tell some exciting travel stories. "Conversations are everything," physician Akshad Singi, M.D., attested. "Even if you have all the money and fame in the world, if you don't know how to have good conversations, you won't have meaningful relationships."

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2. 'What is something about you that you wish people would know?'

Woman has conversation to let people know about herself Monkey Business Images via Shutterstock

By asking this question, you are giving her a chance to really let her be in control of how she likes to be perceived. It allows her to tell you something that you wouldn’t know right off the bat, and it will likely be a fun fact or something that sets her apart from others.

This also lets you see what makes her feel confident and what qualities she values in herself. By letting her show you the way she wants to be seen, she will also feel like she is getting to know you. It also lets you see a different side of her that could have taken you longer to pick up on.

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For example, she might say that she is really good at math. Now that you know this, it will be easier for you to take note of that and even compliment her on her intelligence when it comes up again.

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3. 'If you could give your younger self a piece of advice, what would you say?'

This is a great question because you get to learn about her childhood and what she was like when she was younger without stating the obvious. You also give her the chance to really evaluate what she has learned.

Obviously, we get wiser with age, so this is an illuminating question but also just a fun one to answer. Perhaps she wished her younger self hadn’t worried about what other people thought of her. Now, you can infer that she is more carefree and confident to share her quirkier side.

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Also, this is a great segue into finding out where her answer stems from, and she may even share more without overthinking too much. Either way, this question is bound to deepen your connection and the conversation. 

In productive conversations, explained life coach Susan Petit, "each party is an emotional adult; they take ownership of their actions and move towards the other person with the intent to understand their experience. Lower your guard, come together, and communicate. We are meant to connect with others, and it is up to us to do the connecting from an emotionally responsible, adult place."

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4. 'Are you closer to your family or your friends?'

Woman has conversation about family and friends dekazigzag via Shutterstock

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This question helps you figure out where her priorities lie at the moment. If she is more focused on her friends, then you could find out that she wants to be fun, carefree, and independent at this stage in her life. If she is close with her family, she is more family-oriented, and she might be more inclined to settle down.

Also, be sure to ask why she is more focused on her family or friends, because you get to learn how she spends her time. Asking the reasoning behind her answer is important because you can’t jump to conclusions completely on this one.

Perhaps she is close with her friends because her family lives farther away, and not because she isn’t ready to enter a committed relationship. Instead, this question just helps you see where she is in her life right now, and you get to learn more about her loved ones as well.

Life coach Caroline Maguire explained, "The ability to connect and inspire is an essential human need. In demonstrating respect for our audience, it's essential to learn the critical life skill of being a good storyteller. Equally important is the ability to listen and empathize. Good and open communication is the key to all healthy relationships."

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5. 'What is your dream job?'

By asking her about her dream job, you get to learn what she is passionate about and what goals she wants to achieve. You can learn about what topics pique her interest and what she is motivated by. You also get to see what career path she is on currently and what her dreams are.

In asking about her dream job, you may even learn more about what she is doing now and find out if she is heading in that direction. By learning about her goals, you will know what she is striving for and how to cheer her on along the way.

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When it comes to relationships, you want to have a partner who is also working toward their own goals and dreams, so you both can support each other in achieving these dreams.

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Jaycee Levin is a writer who covers astrology, entertainment, love, and relationships. Her work has also been featured in Inferse.

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