And how to get a conversation going that doesn't need a list of prompts.
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There's no doubt about it: First dates can be really daunting. Even the most seasoned dater can feel equal parts excitement and nervousness as they reach into their closet for the perfect first date outfit that's truly going to "wow" the person across from them. Dating in this day and age — with the political climate, a pandemic that doesn't appear to be going away anytime soon, etc. — isn't easy.

If you don't date often, a first date can feel like a job interview — for both parties. It's important to realize that it's not just about knowing the right questions to ask on a first date, but also how you engage with the person, how you respond, and how you carry yourself.

Here's what you should keep in mind on a date — and, yes, plenty of first date questions to get you started.

Really listen to what your date is saying.

A good conversation (with anyone, date or otherwise) is about listening to the other person. Sitting there just waiting for your turn to speak or keeping a mental checklist of your questions or their answers isn't really listening. When you truly listen to what's being said, even if every answer isn't exactly what you want to hear, your conversation — and this potential relationship — has a better chance of staying afloat than if you tune out.

"When you're present in the conversation, you will be most likely to ask questions based on the material that is naturally coming up, which will create a more fluid, connective, and interesting conversation," says Kim Egel, a licensed therapist and clinical psychologist. "You can't possibly script a conversation without it feeling somewhat generic and out of flow. Paying attention to what the other person is actually saying and asking questions that are guided from the material that is organically coming up will help you to get in flow with the conversation and lead to topics and answers that you couldn't have imagined going toward." (Related: Is It Bad to Google Someone Before a Date?)

This isn't just about keeping things flowing nicely (and avoiding those awkward silences most of us fear), but it's also how you really connect with and get to know someone, says Egel.

Ask questions that dig deep.

While asking your date their favorite food, favorite place in the world, and what they do for work is fun and important in their own way, you want to go beyond that — any possible future relationship can't exist on you both loving pizza and the color blue, after all. A conversation that digs deep and includes good first date questions that cover the important stuff, as well as funny first date questions (because humor goes a long way), can really give you insight into who your date is — from their values, to their fears, to their favorite joke.

"Ask questions that help you get an idea of what this person has been doing with their time," says Egel. "Pose questions that help you get an idea of this person's hobbies, level of adventure, passions, priorities, and relationships with family and friends. All these areas define a person and can give you a lot of insight around what is important to them."

A lot can be realized about a person on a first date. So if the conversation goes well, in that you cover the necessary first date questions and are present, you can know by night's end whether you want to see them again. (When you're past the first-date stage, consider these flirty, sexy, romantic questions to ask your partner.)

Give them some wiggle room in their answers.

When you're trying to make a good first impression, your brain can feel like it's all over the place. What this means is that not every question posed — by either of you — or every answer is going to be perfectly articulated.

"The reality is that when you're asking questions about the other person, their answer only matters to a certain extent," says Canwen Xu, a dating expert at Iris, an AI dating app. "Sure, you might evaluate the substance of what they say, but you're also sussing out the chemistry. If the two of you naturally have an organic banter and conversation flow, chances are the content of their answers may not matter as much as you would think."

Naturally, if your date tells you that they're racist or sexist, there's no need to extrapolate what they "actually" mean. What they mean is exactly what they just said.

It's totally okay to have dealbreakers.

It doesn't matter if you're 25 or 45, there's a pretty good chance you have at least a few dealbreakers when it comes to dating — and you should! Knowing what you can look past and what you absolutely can't, isn't just about finding the right person, but also standing by your convictions. (See: How to Set Boundaries with Anyone In Your Life)

"We all have different qualities that are important to us when we're dating," says Egel. "Simply said, we all have different dealbreakers and the right first date questions can help you gain more insight about your date."

Even if your friends think your dealbreakers are silly, that's fine. You don't want to date someone who only wears white socks and hates wasabi? That's your call. (Related: How to Manifest Love — and the Kind You Deserve)

Realize it's not just about you.

Although you might be putting your needs and wants first in this first date conversation, take the other person into consideration, too. I mean, they might end up being someone you actually date.

"Dating is a two-way process," says Xu. "You can decide you don't want to see the other person, and they can do the same to you. It's all about mutually figuring out whether the other person is the right fit. For instance, you probably want to know whether your date is more of a homebody or more the adventurous type, and they also want to know the same about you. So it's not just about hearing what they have to say and whether that meets your criteria, it's also about finding out whether you both think there's room for compatibility." (Related: The Best First Date Ideas for Every Zodiac Sign)

Also, keep in mind that there's a very good chance your date is just as nervous as you are, so that should provide some comfort as you try to figure each other out.

Ready to take these tips and put them into action? Here are 50 of the best first date questions, according to experts. And because this isn't an interview, just let the conversation flow and don't think these need to be covered in any particular order.

50+ Questions to Ask On a First Date

  1. What do you do when you have downtime?
  2. Are you more of a party person or stay-at-home person?
  3. Are you an animal person?
  4. Dogs or cats? Why?
  5. What are you looking for in a relationship?
  6. What's your biggest regret so far in life?
  7. What's your most embarrassing moment?
  8. How do you handle rude people?
  9. Where did you grow up?
  10. Are you close to your family?
  11. Do you have any siblings?
  12. Do you live near your family? How often do you see them?
  13. What was the best part of your day today?
  14. What's your favorite food?
  15. Are there any great restaurants in this area that you would recommend?
  16. What did you do during the Covid lockdown? Anything you wish you'd done differently?
  17. What's the most adventurous thing that you've done?
  18. What's on your current playlist?
  19. Do you keep in touch with your friends from your hometown?
  20. How do you feel about traveling?
  21. Where has been the most beautiful place you have travelled?
  22. What was the last book you read?
  23. What's the best film you've seen this year?
  24. What's your favorite drink?
  25. What's your dream job?
  26. What have you done that you're really proud of?
  27. What do you want to try or do in life that you haven't yet?
  28. When was the last time you got super angry with someone? What happened to make you that angry?
  29. Do you prefer to be alone or with friends when you're sad?
  30. Would you date someone whose social media presence made you cringe?
  31. Are you a morning person or a night owl?
  32. When was the last time you laughed until it hurt?
  33. What are you most passionate about?
  34. What was your dream job when you were a kid?
  35. What's your motto?
  36. How did you meet your best friend?
  37. What are you known for among your group of friends?
  38. What's something from your past that still makes you cringe?
  39. What skill do you want to learn?
  40. What is the first thing you look for in a potential partner?
  41. If tomorrow was a snow day and work was canceled, what would you do with your day off?
  42. When in your life were you most happy?
  43. What magazine, website, etc. subscriptions do you have?
  44. Are you more into binging podcasts or a Netflix series?
  45. Do you think people are inherently good or bad?
  46. How important is trust to you?
  47. What are your thoughts on religion?
  48. Would you say you're political or apolitical?
  49. When was the last time you splurged on an expensive treat for yourself?
  50. How important is alone time to you?
  51. What would you do if I had something in my teeth right now?
  52. If you could have any wild animal as a pet, what would you choose?