30 Questions You Absolutely Want to Skip on a First Date
First dates are already nerve-wracking enough. Between figuring out what to wear, overthinking if you should text âIâm hereâ or walk straight in, and praying they look like their pictures, who has time to worry about asking the wrong questions?
Well⌠you should. Because nothing derails a date faster than a poorly timed, awkward, or downright weird question. Some make things too serious, too soon. Others make you sound like an undercover detective. And a few? Theyâre just yikes.
So, before you accidentally ask your date about their deepest childhood trauma before the appetizers even arrive, here are some questions you should absolutely avoid on a first dateâplus better conversation starters to keep things fun, flirty, and non-cringey.
1. What’s your salary?
Asking about someone’s salary on a first date is like bringing a calculator to a poetry recitalânot the vibe you’re going for! This question can make the other person feel like they’re sitting for a financial interview rather than enjoying a potential love match. It’s a topic best reserved for when you’re deeply embedded in each other’s lives, not when you’re just getting acquainted.
Focus on getting to know what theyâre passionate about in their career or hobbies. These topics can open up conversations that are both enlightening and enjoyable. Remember, it’s about connection, not compensation.
Keep the conversation light and engaging by asking about their favorite projects or what they find most rewarding about their job. This way, you can gauge their enthusiasm without turning the date into a tax audit.
2. How many kids do you want?
Jumping into the topic of kids on a first date can be like fast-forwarding to the end of a movieâyou miss all the important stuff in between! This question can intimidate or pressure your date, especially if they’re just getting to know you. It’s a hefty topic, layered with personal, cultural, and lifestyle nuances that deserve more than a cursory glance over appetizers.
Choose lighter topics, such as travel experiences or favorite books, which can reveal a lot about someone’s values and interests without the heavy commitment talk. Asking about kids can wait until you’re both more comfortable discussing long-term life plans.
Keep it breezy and save the kid conversation for another time.
3. Why are you still single?
Asking someone why they’re still single is like opening Pandoraâs box of past relationships and life choices. It can make your date feel like they’re on trial rather than enjoying a pleasant outing. This question can come across as judgmental, implying there’s something wrong with them, rather than respecting their personal journey.
Everyone has their reasons for being single, and they don’t need to justify it on a first date. Ask about their hobbies or interests, which can lead to lively and revealing discussions. Understanding what makes them tick is far more enjoyable than dissecting their relationship history.
The goal is to see if there’s a connection worth exploring, not to psychoanalyze their single status. So, lean into the fun side of getting to know them, and leave the social interrogations for later dates.
4. Are you over your ex?
Discussing exes on a first date is akin to inviting a third wheel to your dinnerâawkward and unwelcome. Asking if someone is over their ex can bring back unresolved emotions and turn a light-hearted evening into a therapy session. It’s a question that can derail the conversation and put your date on edge, as they might not be ready to unpack their emotional baggage in front of someone new.
Instead, focus on the present by asking about their current hobbies or favorite places to visit. This will help you learn about their interests without veering into sensitive territory.
Keep the focus on the present and future possibilities. After all, the first date is about discovering if there’s a spark between you twoânot about unpacking each other’s past heartaches.
5. What’s your political stance?
Diving into politics on a first date is like lighting a match in a room full of fireworksârisky and potentially explosive. Unless you met at a political rally and this is your shared passion, itâs a topic that can polarize and divide faster than you can say “election day.” Discussing political stances can lead to heated debates instead of warm, fuzzy feelings.
Keep the conversation light and fun by asking about their favorite music or recent travel adventures. These topics can offer insights into their personality without triggering a debate. Save the political discussions for when you know each other better and can handle disagreements with grace and understanding.
The goal is to find common ground and enjoy each other’s company, not to wage a mini political campaign across the table.
6. How much do you weigh?
Asking someone about their weight on a first date is like showing up with a list of their insecuritiesâit’s a surefire way to make things awkward. This question can come off as intrusive and judgmental, making your date feel like they’re being assessed rather than appreciated.
Itâs a personal topic that doesnât belong in the early stages of getting to know someone. Instead, focus on conversations that make both of you feel comfortable and relaxed, like discussing favorite movies or recent hobbies.
So, steer clear of sensitive topics and keep the conversation light. Remember, charm is more attractive than a checklist of personal statistics. Aim to make your date feel valued for who they are, not their physical measurements.
7. Why don’t you drink?
Questioning why someone doesn’t drink on a first date can feel like prying into their personal choices and history. It can make your date feel defensive or uncomfortable, as there are often deeply personal reasons behind such decisions.
Instead of focusing on what they avoid, celebrate what they enjoy. Ask about their favorite non-alcoholic drinks or hobbies that bring them joy. Appreciate each other’s uniqueness and find common ground, not to question personal choices.
Use the opportunity to learn about their interests without delving into potentially sensitive topics. Keep the conversation light and respectful, and you’ll likely have a more enjoyable and meaningful first meeting. After all, it’s about building bridges, not barriers.
8. Do you believe in marriage?
Diving into marriage beliefs on a first date is like discussing the ending when youâve only just started the book. Itâs a topic loaded with personal beliefs and dreams that can feel overwhelming for someone youâve just met.
This question can pressure your date to reveal their long-term intentions before youâve even finished your drinks. Steer the conversation towards light-hearted and fun topics like travel adventures or favorite films, which can reveal personality traits and interests without the lifelong commitment talk.
Remember, a first date is about establishing a connection and enjoying each other’s company, not debating life-long commitments. Keep it fun, engaging, and pressure-free to ensure a delightful and memorable first encounter.
9. Do you still live with your parents?
Asking if someone still lives with their parents on a first date can feel like you’re probing into their personal circumstances rather than enjoying their company. It can imply judgment about their independence or financial status, making your date feel self-conscious or defensive.
Discuss topics that celebrate their individuality, like their favorite travel destinations or hobbies. These subjects can lead to light-hearted and engaging conversations that help you learn about each other without delving into personal living arrangements. The aim is to connect and have fun, not to evaluate each other’s life choices.
Leave the practical questions for when youâre more established in each otherâs lives. Keep the atmosphere friendly and relaxed to ensure both of you have a wonderful time getting to know each other.
10. How’s your health?
Asking about someone’s health on a first date can feel like you’re diving into personal territory that they’re not ready to share. It can come across as intrusive and may make your date feel uncomfortable or self-conscious.
Focus on topics that are more appropriate for early-stage conversations, such as favorite books or recent hobbies. The goal is to create an atmosphere where both of you feel comfortable and intrigued by each other’s stories.
Keep the conversation light and engaging to ensure both of you have a delightful time. Enjoy the process of getting to know each other without unnecessary pressure.
11. Do you have any debts?
Asking about debts on a first date is like handing over a financial questionnaire instead of a menu. It’s a topic that can make your date feel uncomfortable and judged rather than valued and respected. Money matters are personal and can create tension if brought up too early in a relationship.
Instead, focus on building a connection through shared experiences or dreams, such as discussing travel goals or bucket list items. Remember, first dates are all about exploring the potential for connection, not auditing each other’s finances.
Save financial discussions for when the relationship matures and both of you are ready to share more personal aspects of your lives. Enjoy the journey of getting to know each other without unnecessary financial inquiries.
12. What’s your most embarrassing moment?
Bringing up embarrassing moments on a first date can backfire, making your date feel exposed rather than entertained. While the intent might be to lighten the mood, it can lead to awkwardness or discomfort, as not everyone is ready to share their cringe-worthy stories right away.
Ask about their favorite memories or proudest achievements. It will allow both of you to share stories that uplift rather than embarrass.
Keep it friendly, relaxed, and pressure-free for the best experience. First dates are about building a connection and enjoying each other’s company, not about putting each other on the spot.
13. What are your parents like?
Diving into family dynamics on a first date can be like opening a book with too many footnotes. Itâs a topic that can quickly become complex and emotionally charged, making your date feel uncomfortable sharing too much too soon.
Instead, ask about their favorite childhood memories or experiences that shaped them. Keep the focus on getting to know each other in a fun and light-hearted way, ensuring the conversation remains engaging and relaxed.
Save the in-depth family discussions for when you have both built a stronger connection and are ready to explore those aspects of your lives.
14. What’s your biggest fear?
Discussing fears on a first date can overshadow the evening with heaviness instead of joy. It’s a topic that’s intensely personal and can make your date feel vulnerable rather than comfortable. Instead, talk about favorite travel destinations or exciting future plans.
First dates are about enjoying each other’s company and discovering shared interests, not about unpacking each other’s anxieties.
Remember, the goal is to create a positive atmosphere that fosters connection and enjoyment. Let the date be about discovery and delight, setting the stage for future conversations.
15. Do you want to get married?
Jumping into marriage talk on a first date is like proposing on the first day of schoolâtoo soon and overwhelming. It’s a question that can pressure your date, making them feel cornered about their long-term intentions.
Connect and enjoy each otherâs companyâdonât rush into planning a future together. Save the marriage conversation for when you both feel more comfortable exploring such life-altering topics.
Keep it light, engaging, and pressure-free to ensure a memorable first encounter. Enjoy discovering each otherâs interests and let the conversation flow naturally.
16. What’s your credit score?
Inquiring about someone’s credit score on a first date can feel like you’re evaluating their financial worth instead of getting to know them as a person. Itâs a question that can make your date feel judged and uncomfortable, turning a pleasant evening into an interrogation.
Talk about light and engaging topics like favorite music or recent adventures. Remember, first dates are about exploring potential connections, not conducting financial audits. Keep the conversation fun and relaxed, allowing both of you to enjoy the moment.
Save the credit score talk for when the relationship has matured and youâre both ready to share more personal details. Enjoy each other’s company without unnecessary pressure.
17. Do you have any unusual habits?
Asking about unusual habits on a first date can feel like you’re fishing for quirks instead of enjoying their company. Itâs a question that can make your date feel self-conscious and on display, rather than appreciated for who they are. Instead, focus on discovering shared interests through topics like favorite books or recent adventures.
The goal is to create a relaxed and enjoyable atmosphere where both of you feel comfortable sharing. Save the quirky habit discussions for when youâve established a deeper connection and trust.
First dates are about discovering compatibility and enjoying each other’s company, not about cataloging quirks. Let the conversation flow naturally, allowing both of you to explore each other’s personality in an enjoyable way.
18. How many people have you dated?
Asking how many people someone has dated on a first date can feel like an audit of their personal history instead of an exploration of who they are. Itâs a question that can make your date feel judged or pressured to justify their past relationships. Instead, focus on current passions and interests, such as favorite activities or recent hobbies.
You can have fun and eye-opening discussions without delving into past experiences. First dates are about finding out if there’s chemistry, not about tallying past romances. Keep the conversation light and engaging, ensuring both of you have a delightful time.
Save the detailed dating history for when youâre both more comfortable with each other.
19. Have you ever been arrested?
Inquiring about arrest records on a first date is like asking for their life story before youâve even finished your coffee. Itâs a question that can make your date feel uncomfortable or judged, rather than appreciated for who they are today. Instead, focus on light-hearted topics like favorite foods or travel experiences.
Keep the conversation enjoyable and pressure-free to ensure both of you have a wonderful time. Save the in-depth personal history for when youâve both built a deeper relationship and trust.
The date should be about enjoying each other’s company and exploring new possibilities, without unnecessary probing.
20. What’s your biggest pet peeve?
Discussing pet peeves on a first date can steer the conversation toward negativity instead of positivity. Itâs a topic that can make the mood feel heavy, as both of you focus on annoyances rather than enjoyment. Instead, concentrate on more uplifting topics like favorite books or memorable vacations.
First dates are about finding potential chemistry and having fun, not about listing grievances. Keep the conversation upbeat and light-hearted to ensure a positive and enjoyable experience. Save the pet peeve talk for when youâre both more comfortable with each other.
Let the date be about fun and connection, not about irritation.
21. Have you ever seen a ghost?
First dates are often about creating a comfortable atmosphere, and asking if someone has seen a ghost can lead to an eerie conversation.
This question might make your date uncomfortable or even frightened, especially if they have had a supernatural encounter. Instead, focus on light-hearted topics that are likely to keep the mood pleasant. Ask about their favorite childhood memories or a heartwarming story that makes them smile.
Sharing positive experiences can encourage a deeper connection and turn the date into a more enjoyable and memorable experience for both of you.
22. If you could have dinner with any historical figure, who would it be?
While discussing historical figures might seem intriguing, it can quickly veer into serious or controversial territory. This could make your date feel like they are being interviewed for a history exam.
Instead, consider asking about the best meal they’ve ever had or a memorable dining experience. This approach can lead to a more relaxed and engaging conversation, filled with positive associations and happy memories.
Sharing stories about delicious food and fun dining experiences can be a delightful way to connect on a culinary level without venturing into heavy historical discussions.
23. What’s the weirdest thing you’ve ever eaten?
Asking about strange food experiences can be a gamble. While some may find it amusing, others could find it off-putting or even disgusting. It’s essential to gauge your date’s comfort level with unusual topics.
A more universally appealing question could be about their favorite dish to cook or a recipe they enjoy trying out. This question not only avoids potential awkwardness but also gives insight into their culinary skills and interests.
Discussing food preferences and cooking adventures is often an enjoyable and relatable topic that can bring a sense of warmth and connection.
24. Would you rather be a vampire or a werewolf?
While the debate between being a vampire or a werewolf might amuse fantasy enthusiasts, it could also appear childish or irrelevant. Such a question might not contribute to building a genuine connection.
A more thoughtful question could focus on their favorite book or movie genre and why it appeals to them. This encourages a deeper, more personal conversation about interests and hobbies.
By sharing preferences and insights, you can create common ground and a more meaningful dialogue, sparking curiosity and understanding between you both.
25. If you could have any superpower, what would it be?
Dreaming about superpowers can be fun, but it could also make the conversation feel childish. Rather than delving into fantasies, consider asking about a personal achievement they’re proud of.
This question invites them to share a positive experience or accomplishment, allowing you to celebrate their success and character. Such discussions are more likely to build a strong connection and provide insights into their values and interests.
Talk about real-life achievements instead of imaginary scenarios, and you’ll have a conversation that feels genuine and encouraging.
26. What’s your most bizarre habit?
Asking about bizarre habits can make someone feel self-conscious, particularly on a first date when they want to make a good impression. Instead, try asking about their hobbies or what they like to do in their free time.
This allows for a more upbeat conversation about interests and passions, encouraging them to share what makes them unique and happy.
By focusing on their positive traits and activities, you can foster a sense of connection and curiosity about one another, paving the way for more engaging and enjoyable discussions.
27. If you could live in any fictional universe, which would it be?
While discussing fictional universes can be exciting, it may come across as escapism or immaturity. It could also lead to a conversation that your date may not relate to if they aren’t familiar with the worlds you mention.
A more inclusive question might be about their dream vacation destination. This encourages daydreaming about real-world adventures and experiences, fostering a sense of excitement and wonder.
Travel aspirations and shared wanderlust are perfect for discovering common interests and sparking lively, inspiring conversations.
28. Have you ever had a run-in with the law?
Asking about encounters with the law can be intrusive and potentially uncomfortable. It’s best to steer clear of topics that might bring up unpleasant memories or make your date feel defensive.
A more thoughtful approach could be asking about a local event or concert they recently attended. This can lead to a lively discussion about shared interests in music or arts, creating a positive and engaging atmosphere.
By focusing on enjoyable and light-hearted experiences, you can keep a cheerful and relaxed vibe, setting the stage for a successful first date.
29. If you could time travel, what era would you visit?
While time travel fantasies can spark interesting dialogues, they might also drift into complex topics like history or science, which not everyone finds engaging. Instead, consider asking about a memorable experience they had that changed their perspective on life.
This question invites them to share transformative moments that reveal their values and growth. Engaging in such discussions can lead to meaningful connections and a better understanding of each other’s backgrounds.
Talking about real-life experiences and insights creates an atmosphere where both of you feel heard and appreciated.
30. What’s the most unusual place you’ve traveled to?
Discussing unusual travel destinations can either be intriguing or alienating, depending on your date’s travel experiences. While it might lead to fascinating stories, it could also make them feel less worldly if they haven’t traveled much.
An alternative question could be about a local spot they love visiting or a favorite weekend getaway. This keeps the conversation grounded and relatable, allowing you both to share local insights and personal favorites.
By focusing on accessible experiences, you create a welcoming environment where both of you can contribute and enjoy.