What Question Do You Wish Someone Would Ask You?

First dates can be nerve-wracking, leaving you wondering why you even agreed to go on one. But as you sit in your empty apartment, clad in your boxers and binge-watching the latest trending show on HBO, you remember the reason: because you’re single. Fortunately, we’ve got you covered with expert advice on everything you need to make a great first impression, from what to wear to where to go. We’ve even compiled a list of 50 conversation starters, curated from real women, so you can leave a lasting impression on your next first date.

Women’s Insights

We reached out to 20 women and asked them about the questions they wish guys would ask on a first date. Here’s what they had to say:

Dive Deep into Aspirations

Lisa M. believes that a guy should show an interest in her goals and future without getting too serious. Asking about her aspirations allows for a meaningful conversation that goes beyond surface-level small talk.

Family Matters

For Cassie R., discussing family is important. How a person talks about their siblings and parents reveals a lot about their character, relationships, and maturity. So don’t shy away from asking about her family.

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Job Talk

Arielle S. wishes guys would dig deeper into questions about her job. Your career is a significant part of your life, so it’s only natural to want to share and discuss it with your date.

Childhood Dreams

Melanie W. finds it intriguing when a guy asks about her childhood dreams. It gives her the opportunity to share her initial interests, how she has evolved over the years, and what she aspires to achieve.

Going Beyond Surface-Level

Adriana P. appreciates it when a guy asks about her likes and interests. First dates tend to stay superficial, so delving into deeper questions brings a refreshing change and makes her more interested in return.

The Importance of Family

Rachel E. emphasizes how crucial her family is to her. So, asking about her family allows you to understand what matters most in her life.

Life’s Priorities

Becky E. encourages guys to inquire about what is most important in a person’s life. Additionally, asking about bucket lists and dislikes can lead to fun conversations and uncover shared interests.

Goals and Dreams

Tracy G. suggests asking about her goals and dreams. Inquiring about her dream job or her aspirations in life opens up a meaningful discussion about her passions and ambitions.

The Power of Thoughtfulness

Evelyn L. suggests asking about her favorite flower and showing up on the next date with it. It’s a small gesture, but it demonstrates thoughtfulness and shows that you pay attention to the details.

Ice Breakers and Games

Gabi Z. loves ice breakers and fun games as they reveal personality without diving too deep. Questions like “Guess who my celebrity doppelgänger is?” can be a great way to lighten the mood and get to know each other better.

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Dreaming of Travel

Rena D. enjoys questions that let her imagine her next destination. Asking her which city in the U.S. she would fly to right now opens up a world of possibilities for further conversation.

Friends Tell a Story

Deb S. believes there’s a lot to be learned about a person through their friends. Once you’ve covered the basics about her, ask how long she has known her closest friends. It provides insight into her social circle and gives you plenty to talk about.

Show Genuine Interest

Brie G. believes that it’s not just about the questions asked, but also about truly listening and engaging in the conversation. Being present and attentive is key to making a real connection.

The Magic of Another Drink

Julia W. suggests that the best question to ask is, “Can I get you another drink?” It’s a question that can gauge her interest in continuing the date. If she accepts, it’s a sign that things are going well, and if she declines, it gives you an idea that she may not be interested.

Closest Confidants

Diane L. believes that asking who she talks to every day speaks volumes. It reveals the people she trusts the most and shows which relationships are most important to her.

Unconventional Questions Lead to Clever Conversations

Sasha M. shares an experience where a guy asked her about her best-ever date, and it led to a clever exchange about good and bad dates. This approach allowed them to plan a second date based on their shared experiences.

The Versatility of Questions

Carissa M. enjoys questions that range from light-hearted to serious, such as “What’s your guilty pleasure?” or “What do you like most about the city you live in?” These questions give her the opportunity to reveal different aspects of her personality.

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Revealing Quirky Facts

Stephanie W. suggests asking, “What’s something I wouldn’t guess about you?” This question uncovers surprising facts about her life, such as being part of a marching band or living abroad, which adds depth to her character.

Adventurous Spirits

Ashley F. recommends asking about the top thing on her bucket list. It not only reveals how adventurous she is but also indicates her willingness to try new and exciting experiences.

Passion and Pursuit

Miranda S. proposes a thought-provoking question: “If you were fired right now from your job, what would you pursue instead?” This question allows her to share her passions, interests, doubts, and fears, providing insight into her true self.

Asking the right questions on a first date can make all the difference in building a meaningful connection. Remember, it’s not just about the questions themselves, but also about actively listening to her responses and engaging in the conversation. So, the next time you find yourself on a first date, try some of these intriguing questions and let the conversation flow. After all, getting to know someone on a deeper level is what makes dating exciting and memorable.

For more insightful content, visit 5 WS.

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