I don’t know about anyone else, but I tend to paint a very rosy picture when I’m about to go on a first date. All of a sudden, the person I’m texting seems to shapeshift, suddenly checking every box I’ve ever had (even if they really don’t).

Turns out, there’s a reason for this chameleon-style phenomenon, says Lisa Marie Bobby, PhD, founder and clinical director of Growing Self Counseling and Coaching. The surge of new crush energy can make it so easy to get swept up in the moment.

On the flip side, sometimes, you can be too quick to assume that because the first drink conversation doesn’t have your stomach exploding with butterflies, that person isn’t "The One."

"When meeting a potential partner for the first time, have great respect for everything you do not know," Bobby advises. It's important to bridge the gap between the two of you and determine whether you're a good fit for each other. How you begin the bonding process—getting familiar with their values, character, and goals—is critical to establishing the solid foundation on which ever relationship should stand.

Well, damn. How do you do that?

By asking questions, says Tara Suwinyattichaiporn, PhD, sexual communication and relationship expert, and professor at California State University, Fullerton. And though posing a ton of questions to someone you've just met can seem daunting, it's totally possible to deliver them in a way that feels natural and not interrogative. If you're still iffy on your ability to lead a conversation that's not #awkward, Suwinyattichaipornalso encourages a pre-date routine that includes saying affirmations like "I am sexy" or "I am interesting" while you think of some questions or conversation topics for the date.

"People are naturally drawn to confident people," says Suwinyattichaiporn, so this practice will put you in the right mindset for asking those all-important Q's.

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. "It’s a good way to get a sense of who the person really is." Basically, if you're trying to truly connect with your date, asking questions without making it seem like a pop quiz is the way to go, Tracy says.

Keep reading for 163—yes, 163!—expert-approved questions you can ask on a first date. (Thank me later.)

Ice Breakers

If you're nervous about how to ease into asking questions on your date, Tracy recommends starting with some softball Q's. For example, hit them with some easy ice breakers that can relieve any anxiety. (See also: 250+ Questions To Ask To Get To Know Someone Better.)

    1. What made you want to go on this date?
    2. Who's your closest friend and why?
    3. Would you rather spend a night in with your partner or go out in a large group?
    4. What's one of your favorite childhood memories?
    5. Why did you decide to move to this city or town?
    6. Where is your favorite place in the world?
    7. What's your favorite local spot?
    8. What neighborhood do you live in?
    9. If you could go out to dinner with anyone in the world, who would it *not* be and why?
    10. What are the greatest and worst books you've ever read?
    11. Do you have a favorite author? If so, who?
    12. What's your favorite movie or television show?
    13. What's the best meal you've ever eaten?
    14. What's the best vacation or trip you've ever been on?
    15. What's your favorite sports team and why?
    16. What was your AIM screen name?
    17. What are you looking forward to right now?
    18. What’s on your bucket list?
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      Work Questions

      It can be boring to only talk about work on a date. That said, a person's job does take up a large part of their life, so it's no surprise that you're going to have to ask them about their occupation to learn more about them. Wanna make sure this part of the convo doesn't become a snooze fest? Tracy suggests getting creative: "Instead of only asking 'Where do you work?,' try asking 'Who do you hang out with most at work?' or 'What’s next for you in your career?'" This keeps the conversation light, so the date doesn't seem like a job interview.

      1. Where do you work?
      2. How long have you been in this profession?
      3. Who do you hang out with most at work?
      4. What do you love most about your job?
      5. What do you like the least about your job?
      6. What's next for you in your career?
      7. Do you want to grow within your company, or do you see yourself elsewhere?
      8. How did you decide to follow this career path?
      9. What did you study in school?
      10. What's your greatest professional accomplishment?
      11. What's the most embarrassing thing that's happened to you at work?
      12. Who is your least favorite colleague and why?
      13. Who is your professional role model or inspiration?
      14. What does a typical workday look like for you?
      15. How do you get along with your bosses?
      16. How do you think your career does (or doesn’t) fit your personality?
      17. What’s the hardest thing about your job?
      18. How has your role changed since getting hired?

      Personality Questions

      When it comes to personality-based Q's, Tracy says the key is to ask them about situations. This way, you get a chance to see how they might react in certain positive, negative, or neutral scenarios, which may reveal more about who they are than asking them point-blank about their music tastes or pet peeves.

      1. Are you an introvert or an extrovert?
      2. Are you an early riser or a night owl?
      3. What does an ideal weekend look like for you?
      4. What's your favorite way to relax?
      5. How often do you like to exercise?
      6. How would you describe your personality?
      7. Do you like to relax or explore while on vacation?
      8. What's your biggest pet peeve, and how do you respond when it happens?
      9. What kinds of things make you the most upset?
      10. What do you act like when you're sad or mad?
      11. What makes you happy?
      12. How do you communicate your feelings to others?
      13. Who do you go to when you need to vent?
      14. Do you consider yourself a calm or anxious person?
      15. What do you like most about yourself?

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      Family Questions

      Okay, so family can be a sore subject depending on the person's relationships. Still, if family is super important to you, you'll want to get some background on how a potential partner interacts with theirs, how close they are, and so on. If you're worried about bringing it up, before you ask, you might want to confirm that it's okay to talk about their family circle, Tracy says.

      1. Do you have any siblings?
      2. How close are you to your siblings?
      3. Who were you raised by?
      4. Are you close to your parents and/or grandparents?
      5. What's it like being around your parents?
      6. How close are you to your immediate family?
      7. How often do you visit your hometown?
      8. How close are you to your extended family?
      9. What was it like growing up in your family?
      10. What was the best part of your childhood?
      11. What were you like in high school?
      12. What's your most embarrassing childhood memory?
      13. Who was the most important part of your youth?
      14. Are you still friends with people you knew growing up?
      15. How would you describe your family to someone new?

      Questions About Values

      "It’s hard to avoid topics like religion and politics," Tracy says. "[But] It’s more acceptable to talk about those things on a first date [these days]." Concerned about bringing up a touchy subject? Ask them if it's cool to talk values before you dive right in, Tracy suggests. Once you get the go-ahead, it's time to dig deep.

        1. What's your political affiliation?
        2. Who do you plan to vote for in the next election?
        3. Has your political affiliation changed?
        4. What's the social issue you're most passionate about?
        5. What was your life like during the COVID-19 quarantine?
        6. How religious are you?
        7. Were you raised practicing a specific religion?
        8. How important are holidays to you?
        9. What would you consider to be your personal values?
        10. Who are the most important people in your life?
        11. What brings you the most fulfillment in life?
        12. Do you live to work or work to live?
        13. How important is alone time?
        14. How important are other people's values to you?
        15. What role do your friends play in your life?
        16. Who do you admire?
        17. What would you tell yourself five years ago?

        Questions About Passions and Hobbies

        "Hobbies show their personality, extracurriculars, and values in life," says Tracy. And if your hobbies align (maybe you both like to read!), there's a chance you can do them together.

        1. What do you do in your spare time?
        2. What are your hobbies?
        3. What is the hobby you've been doing for the longest period of time?
        4. What's a recent hobby that you've picked up?
        5. How often do you read?
        6. How important are hobbies to your mental health?
        7. What's a hobby you'd pick up if you had more time?
        8. What do you consider to be your passion in life?
        9. How passionate are you about your job?
        10. When do you make time for your hobbies and passions?
        11. Is it important that your friends share your passions?
        12. What do you consider your biggest contribution to the world?
        13. How do you want to feel at the end of your life?
        14. What's something you're really proud of?
        15. If you could do one thing for the rest of your life, what would it be?
        16. What is it about your hobby that you are drawn to?

        Relationship Questions

        If you know what hasn't worked in past relationships, then odds are you'll be able to spot those red flags in this relationship, too. "You can mold the information you gather from the first date to determine whether you want a second one," Tracy explains.

        1. What are you looking for in a relationship?
        2. What does your ideal partner look like?
        3. What do you like most about relationships?
        4. What's the best part of dating you?
        5. How do you cope with loneliness?
        6. Who do you go to for relationship advice?
        7. What's the best love advice you've ever received?
        8. Do you like dating apps?
        9. What made you want to start dating?
        10. What was your longest relationship?
        11. What was your shortest relationship?
        12. What's been your greatest heartbreak?
        13. What's romantic to you?
        14. How do you know that you like someone?
        15. Have you ever lived with a significant other?
        16. What is your biggest pet peeve in a relationship?
        17. What are your love languages (to give and receive)?

        Questions About Future Plans

        A lot of the tougher questions with hard-to-crack answers come when you ask about future plans. If you aren't on the same page, it could signal some issues long-term—and save you both from wasting time on an incompatible match now.

        1. What are you looking for in a serious relationship?
        2. How worried are you about the future?
        3. Where do you want to be in five years?
        4. What about the future excites you most?
        5. What about the future concerns you most?
        6. Where do you want to live eventually?
        7. Do you ever think about having kids?
        8. What kind of a parent do you think you would be?
        9. How important is it that you live close to your family?
        10. What's your opinion on marriage?
        11. How often do you want to travel for pleasure?
        12. Is there anywhere in the world you haven't seen yet that you'd like to?
        13. What's your ideal style for a home?
        14. Is there anything you hope to do more of in the future?
        15. What's something you'd like to get better at in the future?

        Sexuality Questions

        Sex! There's no doubt that this can be an awkward subject. But if the date has been going well, you can consider bringing up a more ~sensual~ topic. Before asking something potentially uncomf, Tracy says to read the room and ask yourself if you're in the right headspace to give answers, too.

        1. How would you describe your sexual orientation?
        2. How would you describe your tastes in the bedroom?
        3. What do you look for in a sexual partner?
        4. How do you define the word 'sex'?
        5. When was the first time you had sex?
        6. What was your first kiss like?
        7. What's your greatest sexual fantasy?
        8. Who's your celebrity crush?
        9. Do you believe in casual sex?
        10. Do you enjoy talking about sex?
        11. How old were you when you had your first crush?
        12. What does sex typically mean to you?
        13. What's your biggest turn on?
        14. What's your favorite movie sex scene?
        15. Is there anything you wouldn't do in bed?
        16. What do you think about sex on the first date?
        17. What do you think about sexual exploration for couples?

        Now It's Your Turn

        So you've asked your date a bunch of questions. One way to take the heat off of them is to turn your Q's inward. Start posing inquiries that have to do with what they think of you. It will give them a chance to flirt with you (hi, compliments!) while also making sure the convo isn't all about them.

        1. What was your first impression of me?
        2. What stood out about my dating profile?
        3. What kind of friends do you think I have?
        4. What do you think my parents are like?
        5. Why did you decide to go on a date with me?
        6. If I were an animal, what kind would I be?
        7. What's your favorite thing you've learned about me so far?
        8. What's your least favorite thing you've learned about me so far?
        9. What's been your favorite part of this date?
        10. Do you think we have things in common?
        11. If we went on another date, where would we go?
        12. What celebrity do I remind you of most?
        13. What stood out to you most during this conversation?
        14. When did you know you were going to enjoy this date?
        15. Anything you want to ask me?