Ah, the famous first date. Is there anything more nerve-wracking (mortifying? nausea-inducing?) than meeting a potential partner for the first time?
If you’re freaking out, take a deep breath—it’s totally normal to feel nervous before a first date, especially if it’s the first time you’re meeting this person IRL (thank you, dating apps!). Even if you did meet at a party or through a friend, you still don’t know much about their personality, so it can be totally intimidating to think about how you’re going to conduct a conversation. But instead of feeling apprehensive, simply consider this an opportunity to learn about someone new. “When meeting a potential partner for the first time, have great respect for everything you do not know,” says licensed psychologist Lisa Marie Bobby, PhD.
What’s the best way to offer that respect and get better acquainted with a cutie at the same time? By asking questions, of course. Asking thoughtful questions exudes confidence, and “people are naturally drawn to confident people,” says sexual communication and relationship expert Tara Suwinyattichaiporn, PhD.
And, not for nothing, “open-ended questions allow the other person to express their true, authentic self,” says Courtney Tracy, LCSW, PsyD, a therapist and relationship expert based in California. “It’s a good way to get a sense of who the person really is.”
Meet the Experts:
Lisa Marie Bobby, PhD, is a licensed psychologist, and the founder and clinical director of Growing Self Counseling and Coaching.
Tara Suwinyattichaiporn, PhD, is a sex and relationship expert, and professor of relational and sexual communication at California State University, Fullerton.
Courtney Tracy, LCSW, PsyD, is a licensed therapist and relationship expert based in California.
Rachel Moheban-Wachtel, LCSW, is a couples and relationships therapist serving clients in New York and New Jersey.
Victoria Riordan, LPCC-S, is a couples and marriage counselor based in Columbus, Ohio.
Brooke Schwartz, LCSW, is a psychotherapist specializing in relationships based in Los Angeles, California.
On the first date, you should also prioritize your own time. “You want to make sure you are ruling out something you’re not interested in,” says Rachel Moheban-Wachtel, LCSW, a licensed therapist who specializes in couples and marriage counseling. “You need to make sure that you are getting what you need out of the date, too.” Meaning, if you want a life partner, you might want to ask your date if they’re ready for a relationship, or find out if they just went through a breakup.
Just remember: A first date should not be a job interview with cocktails. And, let’s face it…it can be hard to get to know someone via questions without it feeling like an interrogation. To create a natural convo that ebbs and flows, make sure to strike a balance between asking them how they like to spend their time and getting to know the nitty-gritty deets of their life (like, uh, how they handle conflict).
So, what exactly should you ask on a first date? “When I think of this question, I think of what is appropriate to bring up and what isn’t,” says Victoria Riordan, LPCC-S, a couples and marriage counselor based in Ohio. “I put them in categories: questions to see if you’re both compatible in your values, your overall goals in life, and your personality to see if you have the skills needed in a relationship.”
Not sure where to start? Look no further than these 15 expert-approved questions to ask on a first date. (Thank me later.)
1. What made you interested in going out with me?
Okay, hear me out. A question like, “Do you like me?” on the first date is a surefire conversation ender, “whereas an open-ended question like this one can start a conversation and lead into another question,” says psychotherapist Brooke Schwartz, LCSW.
By understanding what stood out to them about you—whether it’s something you shared on your Hinge profile or randomly at the coffee shop you met—you can get to know what sparks their interest a little better. This question is also a little flirtatious, which can ignite a nice li’l spark at the beginning of your date.
2. What are you looking for?
The point of this question is to gauge whether your dating goals are aligned. “Whether you’re looking for a casual hook up or a life partner, [their] response will give you a clue as to what they’re looking for,” says Schwartz. This information is especially helpful to know if you’ve already been on a few fruitless dates with others. Don’t be afraid to be direct about your dating goals—it’s a time saver.
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3. What matters to you?
“Asking questions that are too specific like, ‘What are your hobbies?’ can unintentionally isolate the other person. Maybe they don’t have hobbies. But asking what matters to them will solicit a response for sure,” says Schwartz. Maybe they’re really invested in a TV show (uh, Selling Sunset anyone?) or they’re super into health and wellness and can talk for days about this new workout class they’ve been taking. “At baseline, any question that gets at the other person’s values is useful,” Schwartz adds.
4. When you think of recent big political events, is there something that stands out to you?
With this question “you’ll see if you’re compatible with the way you see the world. [And] those tend to be big deals for people,” says Riordan. The age-old dating rule to not talk about religion or politics on the first date is kind of outdated, TBH. If it matters to you, you should ask about it, Riordan adds. “If they can’t handle difficult conversations, that’s not a good foundation for a romantic relationship. The kind of person that is ready to date you is the person that can handle a question that’s a little uncomfortable,” she says.
Especially “if they are make-or-break points for you, it’s worth asking,” Schwartz adds. “It’s better to know upfront.” And if you notice them brushing off the question or skirting around it, then you’ve got your answer, she says.
5. What does your work-life balance look like?
“This question has a lot to do with figuring out if [they] have the skills to be in a healthy relationship,” says Riordan. Are they willing to make time for a relationship? Do they put off important social engagements for work? These are all important things to know about a potential future S.O. because you don’t want to be with someone who’s going to consistently cancel on dates because they were hanging out late at the office or who’s going to put work before your ‘ship.
A great follow-up question to that is: “What does your life look like five years from now?” says Riordan. Do you fit in their current schedule and their future plans? These back-to-back queries allow you to take a deep dive into their life, including whether they’re ready for a balanced relationship—if that’s what you’re looking for right now.
6. What would you do if you had a week off?
“This gives you an idea of what they like to do in their free time and what they value most,” says Schwartz.
Maybe they have the travel bug, and they’re interested in learning about other cultures, so they might book a trip during that time. Or maybe they would prefer to kick back at home and spend time with their dog. At any rate, this is a quick way to see if you have similar vibes when it comes to your downtime without having to ask that question directly. “It also opens the conversation to other questions and keeps the conversation flowing,” Schwartz adds. Plus, thinking of free time may work up a smile.
7. When you spend time with people, how often are you the one making plans?
Or, “When you’re planning things with friends or family, how often are you the one doing that?” says Riordan. This question can make you privy to the other person’s communication style and what role they tend to take on in their most intimate relationships. “Sometimes, one person feels they have to do all of it because [the other] person is not good at communicating, or maybe they are good at delegating,” Riordan explains. On the plus side, if your date is more of a planner and initiator, that lets you know they’re responsible and reliable.
8. How well do you feel like you compromise with others?
“You can’t build a relationship if you can’t compromise,” says Riordan. “If you ask them this and they flounder, that tells you something all by itself.” It may not seem like a big deal at the beginning if they’re not budging on ice cream flavors, for example. But when it comes to long-term issues and decisions, it could lead to a rocky road (get it?).
If you do bump into a my-way-or-the-highway type of person, they may have some maturing to do before they’re ready to date. After all, a partnership is a two-way street.
9. What do you think is important for a healthy relationship?
If you’re looking for a serious relationship, this is a great Q to A. “Knowing what your values are and asking about those specific values is how you get to know someone,” says Riordan. “You want to finish that first date with a clear answer of if you want a second.” For example, if you value healthy communication, you’ll want to know if your partner is the type of person to sit down and debrief with you after an argument, or will instead brush it off like nothing happened and move on.
Whether or not they actually do the things they say, at the very least you can find out what they’re looking for and what their idea of “healthy” is.
10. How do you handle conflict?
“If they tell you ‘I don’t know,’ that tells you something,” says Riordan.
The answer to this question lets you know if the other person has the self-awareness to recognize when they’ve hurt someone and where their behavior might need to change, Riordan explains. “We often end up in a relationship thinking that they’ll just learn [these skills]. But with this question, you can acknowledge where their weaknesses lie, and move forward [accordingly],” says Riordan.
Although no one’s perfect, and people can always work on their conflict resolution, if you learn early on that you handle conflict differently, it can provide some much-needed insight into whether that’s a hurdle you’re ready to tackle.
11. What is something in past relationships you needed to work on?
The answer to this question tells you: “Does this person reflect, and how does this person hold themselves accountable?” says Riordan. “If they answer by casting the blame on everyone else, it’s a red flag.” Make sure you’re screening for potentially toxic traits and looking out for healthy ones—otherwise, you’ll find yourself settling, she adds.
Pro tip: “The sooner you’re able to flag that there isn’t compatibility [between you two] before you’ve gotten attached, the more successful your journey will be in dating,” says Riordan. If you don’t, you might find yourself ignoring your own needs if you catch feelings.
12. Who is the person you talk to the most?
Questions like this are light-hearted and help you understand what relationships the other person values most, says Schwartz. It also offers you breathing room between the heavier questions, too. Plus, you might catch yourself smiling hearing them gush and tell stories about their favorite person.
13. What is the best gift you’ve ever received?
This is another easy-breezy question if you’re reaching for something noncommittal. “It gives them a chance to talk about something they enjoy,” says Schwartz. Maybe they got a new bike because they’re training for a race. Or maybe they were given a telescope because they’re really interested in space. (Spending a summer evening stargazing might make a cute romantic date afterwards, too. Wink-wink)
14. What was your first impression of me?
This is a good question to ask when you’re well into the date. You know, when it’s been a successful evening so far, and you’ve had a quiet moment to reflect. “It can help you get a sense of if they were paying attention [to you] or not,” says Schwartz.
For example, if you’re into sports, and your date responds by saying, “You seem really athletic and like you like hanging out in nature,” you can tell that that person sees you. But if their description is inaccurate in your view, it gives you the opportunity to show your true self—or leave them in the dust if they simply seem uninterested.
15. What made you most excited about going on a date with me?
“This is a jumping off point to share more about yourself,” says Schwartz. This can also lead to questions like, “What’s most important for you to know about me?” and “What’s something totally random you’d like to know about me?,” Schwartz adds. “If they answer with ‘I don’t know, nothing,’ then you have your answer.” (Thank U, next.)
While these first date questions are sure to spark some thoughtful convos, you’re not required to touch on all of these points during your first meeting. The key is not to treat the date as a job interview for the role of your next S.O., but instead to enjoy each other’s company and let the conversation flow naturally. A good rule of thumb when trying to leave your best first impression: “If a question doesn’t feel right to ask, don’t ask it,” says Schwartz. “Sometimes, we get nervous and impulsively ask a question to fill the silence, [but] silence gives you a chance to think more thoughtfully and be more mindful.”
It’s natural for a conversation to have its quiet moments. This is when you might take in things about their mannerisms or their aura, which can tell you as much about a person as their responses to your questions. And “if you are uncomfortable with those random moments of silence, practice role playing with friends,” says Schwartz. That way, you’ll be prepared when those moments inevitably happen.
If you do end up asking a question you regret in an attempt to fill the silence or because you’re feeling jittery, don’t sweat it, you can always change your mind. “You can’t un-ask a question, but it’s always fair to be genuine,” says Schwartz. “You can say you realized that you have a different question that you’d rather ask. There’s nothing wrong with showing fallibility.” After all, everyone’s human, so it’s easy to get too excited and speak before you’ve fully thought your question through.
Just remember: The key to a good conversation is not to listen to respond, but to listen to understand. Whether or not you end up going on a second date, at the very least you can hopefully say you had a good time and connected with a new person. Good luck!
Freelance Writer
Karina Castrillo is a freelance writer, paid leave advocate, communications specialist at a New Jersey-based labor union, and a Libra. She was formerly a travel writer at Culture Trip where she reviewed restaurants and cultural events in both Paris and Miami. Outside of spending a lot of time at coffee shops in the West Village or perusing vintage shops in Greenpoint, you can find her writing her next zine or at a social justice movement rally.
Addison Aloian (she/her) is an editorial assistant at Women’s Health. When she’s not writing about all things pop culture, health, beauty, and fashion, she loves hitting leg day at the gym, shopping at Trader Joe’s, and watching whichever hockey game is on TV. Her work has also appeared in Allure, StyleCaster, L’Officiel USA, V Magazine, and Modern Luxury Media.
Jacqueline Tempera is an award-winning writer and reporter living in New Jersey with her many pets. She is a business owner and a double Scorpio who loves all things astrology and reality television. She is passionate about body diversity and representation, mental health, and the fight to end sexual assault and harassment. To learn more about Jackie, follow her on Instagram @jacktemp or visit her website at jackietempera.com.
