Here's Why Asking Certain Questions Can Make Or Break A First Date, According To Experts
Ah, the famous first date. Is there anything more nerve-wracking (and, oftentimes, mortifying) 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!). But 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. Instead of feeling apprehensive, though, 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.”
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 recently 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 150 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 made you stand out to them—whether it’s something you shared on your Hinge profile, or at the coffee shop where you randomly 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 little 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.
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., since you might not want to be with someone who’s going to consistently cancel on dates because they were hanging out late at the office.
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.)
Need even more ideas and convo starters? Ahead, 135 further questions to ask on a first date.
Basic Questions To Ask On A First Date
16. What does your ideal weekend look like?
17. What do you like to do outside of work?
18. Are you more of an introvert or an extrovert?
19. Do you have any pet peeves?
20. How do you prefer to relax in your free time?
21. What is the best place you’ve traveled to?
22. Do you prefer coffee or tea?
23. Are you a morning person or a night owl?
24. How do you like to wind down before going to sleep?
25. Is there anything you’re scared of?
26. What was your favorite age as a child?
27. Have you ever had any pets?
28. What was your most recent embarrassing moment?
29. If you won the lottery, what would you do with the money?
30. Would you rather spend time in the mountains or on a beach?
31. Who was your favorite teacher in school or college?
32. What is a goal of yours for the next 10 years?
33. Do you usually like nights out or nights in?
34. What is the last book you read?
35. What is your favorite season?
36. If you were stranded on an island, what three things would you bring?
37. What is one skill you’d really like to learn?
38. What are your top music genres?
39. Is there a tradition you loved taking part in as a kid?
40. If you could choose one superpower to have, what would it be?
41. Have you ever traveled abroad?
42. Do you know any other languages?
43. Do you prefer sweet or savory foods?
44. Have you ever met someone famous?
45. What’s something you did when you were younger that you never told your family?
46. Do you have a favorite holiday?
47. If money wasn’t an object, where would you live?
48. Do you see yourself staying on your current career path long-term?
49. Are you someone who likes to take naps?
50. Would you ever relocate for a partner?
Fun Questions To Ask On A First Date
51. Do you have a go-to drink?
52. If you could only listen to one song for the rest of your life, what would it be?
53. What would be your preferred last meal?
54. Would you rather go skydiving or ziplining?
55. What’s your most controversial opinion?
56. What do you usually order for the table?
57. Is there a song you always sing in the shower?
58. Who is your celebrity crush?
59. Have you ever stolen anything?
60. Are you for or against pineapple on pizza?
61. What’s a topic you can rant about forever?
62. Do you still have any favorite mementos from your childhood?
63. What job would you want to have if you could switch careers?
64. If you knew you would prevail, would you rather be a hero or a villain?
65. What is a song that gets you out on the dance floor?
66. If your best friends could give you a dating “review”, what would they say?
67. Do you believe in ghosts?
68. Where can someone find you at a party?
69. What is your go-to midnight snack?
70. Do you always make your bed in the morning?
71. If you drink alcohol, what gets you tipsy the most quickly?
72. What animal would you say best represents you?
73. Do you think hot dogs count as a sandwich?
74. What has been the most wild conversation you’ve overheard in public?
75. If you could time travel, when would you travel to and why?
76. Do you believe in any conspiracy theories?
77. What’s your least favorite food?
78. What would be the title of your memoir?
79. If you had to perform a stand-up comedy set right now, what would you talk about?
80. Do you think you could successfully land a plane in an emergency?
81. Who would you want to portray you in a movie?
82. If a genie gave you three wishes, what would you wish for?
83. What fictional character do you think is the hottest?
84. If you could be the president for a day, what would you do?
85. Do you pour your milk or your cereal first?
Dating-Related Questions To Ask On A First Date
86. If you could travel anywhere for a date, where would you go?
87. What are some non-negotiables you need in a partner?
88. Describe the kind of person your family would want you to date.
89. How long was your longest relationship?
90. Are you a big texter in a relationship?
91. Are you friends with any of your exes?
92. Do you think jealousy is healthy between partners?
93. What are your thoughts on marriage?
94. How long do you want your next relationship to last?
95. What is your love language?
96. How much conflict do you think is healthy in a relationship?
97. Why did your last relationship end?
98. If you’ve ever been in a disagreement with a partner, do you prefer to talk it out in the moment or take some space first?
99. What are three important things you need in a partnership?
100. Is there anything you feel was left unsaid with a former partner?
101. Do you currently view the idea of dating in a positive or negative light?
102. How long do you like to date someone before introducing them to your friends?
103. Do you like double dates?
104. What is your ideal way to spend quality time?
105. Do you think a relationship can work if two people don’t share the same political beliefs?
106. How long were you single after your last breakup?
107. Do you believe in love at first sight?
108. How much alone time do you typically need?
109. Have you ever lived with a partner?
110. Would you ever buy a house with a partner you weren’t engaged or married to?
111. Would you ever move somewhere for a partner?
112. How well did you and your most recent ex communicate?
113. Do you want to have kids?
114. Do you care if your partner makes significantly more money than you?
115. What’s your ideal third date?
116. Do you consider yourself a romantic person?
117. Have you ever experienced true love? How do you know?
118. Do you believe in unconditional love?
119. Have you ever had a relationship end over a deal breaker?
120. Is it important that your partner get along with your friends or family?
121. What does a successful relationship look like to you?
122. Do you prefer to have separate friend groups from your partner?
123. Do you think it’s OK to flirt with others when you’re in a relationship?
124. What is your opinion on going through a partner’s phone?
125. Would you stay in a relationship if your partner cheated?
126. What are your thoughts on couples therapy?
127. Is there a couple you look up to as a model for healthy relationships?
128. What are some of the most attractive qualities to you in a partner?
Thoughtful Questions To Ask On A First Date
129. What core values are you looking for in a partner?
130. Is religion important to you?
131. Who is the person you look up to the most?
132. Do you think that world peace is possible?
133. How do you contribute to your community?
134. Have you ever experienced a major hardship, and how did you overcome it?
135. Do you feel fulfilled by your job?
136. What are three things that really get you out of bed in the morning?
137. Do you believe in astrology? Why or why not?
138. If you could turn back time, is there anything you would do differently in your life?
139. Where do you stand politically?
140. Are you a family-oriented person?
141. Who is your best friend, and why are they your best friend?
142. How do you practice self-care?
143. Have you ever been to therapy?
144. Do you try to surround yourself with people who encourage you to stay open-minded?
145. Is staying informed about current events important to you?
146. When was the last time you cried?
147. What is your greatest strength?
148. If you’ve ever been in love, what made you fall into it?
149. What is your personal definition of success?
150. Do you think most people are generally good?
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.
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