• IJL Team Member Madison

First Date Conversation Starters

First dates can be stressful, not to mention a little awkward if the conversation lulls or you run out of things to say. Here are some first date topic pointers, along with 40 first date questions you can ask to get to know your date a little better.

Starter questions:

You have to start somewhere, and simple get-to-know-you questions are a great way to begin. But, starting with the typical “where are you from?” or “what do you do?” can seem boring and bland, which is why we suggest you spice it up a little.

  1. Compliment your date: This is a great way to begin; you can never go wrong telling your date that they look great. Who doesn’t love hearing that? One could argue that this isn’t actually a question, however it’s an indirect and playful way to make your date feel a little more comfortable and encourage some more genuine conversations. These little things can seem like they’re not important, however giving your date a quick compliment can encourage them to open up a little more and begin the date on a positive note.

  2. Ask follow up questions: This is crucial to keep the conversation natural and flowing. If you only ask a bunch of yes or no questions with no follow up you won’t get to know your date very well, and it may make it seem like you’re uninterested. Make sure there is a balanced flow of conversation on your date. Talking too much may make it seem like you are full of yourself, and not engaging may make it seem like you’re uninterested or bored. Make sure you’re aware of these things in order to have the most successful experience possible.

  3. Be flirty: If you’re having a good time and your date says something suggestive or playful, go with it! Even if it wasn’t executed perfectly, acknowledging that your date tried will make him or her feel more comfortable and will demonstrate that you’re interested. If you’re having a good time there’s not harm in making sure your date knows it.

  4. Be polite: This is another rule that seems obvious but is nonetheless very important. This includes date etiquette. Make sure not to discuss past relationships, or if this comes up, make sure to handle it gracefully and with class. No matter how long ago it was that you dated someone, if you bring them up in conversation or talk about them extensively it will give your date the impression that you’re still attracted or interested in this person, which is a huge turnoff. When going out with someone new, make sure you put all past relationships behind you.

40 Questions to ask on a date

We understand that even if the date is going as smoothly as possible that it there can still be unanticipated lulls in the conversation. If this happens we have several fun questions that can change the subject, and can get your date (hopefully) excited to discuss something new and get to know you a little better. You do not need to ask all 40, this list is simply meant to help you start the conversation and keep it interesting.

  1. Do you have any pets?

  2. What are your siblings like?

  3. What’s the coolest place you’ve ever visited?

  4. What were you like in college?

  5. What is something you’re interested in that you haven’t pursued?

  6. What’s your favorite book/movie?

  7. What’s your family like?

  8. What’s the funniest/most embarrassing thing that’s ever happened to you?

  9. How did you end up at your current job?

  10. Assuming you were secure financially, what would your perfect job be?

  11. What were you like in high school?

  12. Where did you grow up?

  13. What’s your favorite childhood memory?

  14. Are you a morning person or a night owl?

  15. What’s your favorite holiday?

  16. Can you speak any other languages?

  17. If you could live anywhere where would it be?

  18. What’s your favorite cocktail/wine/beer?

  19. What’s your best friend like?

  20. What’s the most spontaneous thing you’ve ever done?

  21. What does your perfect breakfast look like?

  22. What’s something you want to do in the next 5 years?

  23. Who has been a huge influence/made a huge impact on your life?

  24. What’s your favorite thing to do?

  25. What is the most thoughtful gift you’ve ever given someone?

  26. What’s your favorite food?

  27. What’s something you would consider a big accomplishment/obstacle you’ve overcome?

  28. Do you have a nickname/is there a story behind it?

  29. What’s your favorite thing to do on the weekend?

  30. What’s your favorite restaurant?

  31. What’s your favorite show and why?

  32. What’s your pet peeve?

  33. Who was your favorite teacher or college professor and why?

  34. What’s your favorite thing about living here?

  35. What’s something that you’re really bad at?

  36. What combination of ingredients makes the perfect burrito?

  37. What’s something on your bucket list?

  38. What’s your favorite animal?

  39. What does your happy place look like?

  40. What’s something you’re looking forward to this year?

Give these questions a try next time there’s a lull in the conversation. Even if they seem a little corny at first, during your date dropping these into a conversation will seem more natural, and will encourage your date to open up a little more. Not only are these genuine, but they are open ended and could lead to other questions and more interesting conversations.


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