14 First Date Questions To Keep The Conversation Flowing

First dates can potentially be awkward if you don’t have anything to talk about or if there are too many long silences. You know what happens: You both start looking around the room or grabbing for your phones. But if you anticipate that this could happen, you can do something to prevent the dreaded silence that leaves the two of you floundering.


How do you do that? Easy. Just have a few first date questions in the back of your head. Think about them when you’re picking out your date outfit. This backup plan keeps the date interesting if the conversation wanes or gets boring.

Good first date questions are open ended, fun, and tend to be statements instead of questions (which can come off like an interview). Bad first date questions are ones that require only a “Yes” or “No” answer, are too serious, or are too invasive. There are a number of questions you want to avoid asking guys. But you could pepper in a “Would You Rather” question. More on that here.

Keep in mind, however, that if the conversation naturally flows, you don’t need to pull out these preplanned questions. But if you feel that awkward silence coming on, you will now be prepared with 14 great first date questions. You don’t have to ask them all. Pick a couple you really like, and go from there.

1. What do you like to eat when you’re home alone?

This first date question is something everyone can relate to, it’s funny, and it’s an icebreaker. Some people eat cereal at night. Some make crazy concoctions. Some like to eat cold pizza or a bologna sandwich. Or maybe your date is a great cook, and his answer will surprise you. This question can easily veer to a discussion about one of you cooking a meal for the other one. And this can be your second date.

2. What do you like best about the town you grew up in?

This first date question will probably get you a more interesting response than simply asking where he’s from. Plus, if you’re not familiar with the area he’s from, you will have nothing to say except for maybe that you’d like to see that part of the country. Of course, if you are from the same area he is, you’ll have lots to discuss. If you ask this question this way, however, hearing what he likes best, it opens the discussion to other topics besides the town and gives you some insight into his interests.

3. Which movie or movies have you seen more than once?

This question for a first date is another way of asking what his favorite movie is, but it’s more fun for him to think back on what movie he has liked enough to see multiple times. Plus, if he’s seen a movie more than once, he probably knows it pretty well. If you’ve not seen it, he can give you a good description of it and why he likes it so much. And if you’ve seen it, you can talk about what you liked or didn’t like about the movie and why.

4. What’s the most embarrassing concert you attended?

Your date might have a guilty music pleasure, or maybe he was just being a good sport when he took a date to see Justin Bieber. This question for a first date is fun because it gives your guy a chance to talk about what his likes and dislikes in music are. And he can admit whether he actually liked the concert.

5. Which holiday is your least favorite?

This first date question is a spin on the classic question of which holiday is your favorite. When he answers which holiday he doesn’t like, there must be a reason. Then you can share yours. This could naturally lead to a discussion of your favorite holidays. You can talk about how you celebrate them.

6. Do you read reviews?

Some people are researchers and wouldn’t think of buying something, watching a movie, or going to a restaurant without first reading reviews. While others just go with the flow and use their instincts. Find out which he is, or if he’s a little of both. This should open an interesting discussion of why or why not he reads reviews first.

7. What class do you wish you took in school but didn’t?

Maybe he always wanted to learn about forensic science and how to solve crimes. Or maybe he wishes he took computer programming or financial management. Maybe he has no regrets and loves what he’s doing. You can find out by asking this first date question.

8. Are you a dog person or a cat person? Or do you not like pets at all?

Most people have an opinion on this, so it’s interesting to find out which one he is and why. For example, if you’re a pet person and he isn’t, you might not be all that compatible, depending on how important this is to you. Generally, dog people are more social than cat people, and dog people are used to doing more work to care for their pet. Cat people tend to be self-sufficient and are more intellectually curious and sensitive. You can talk about whether those generalities apply to him.

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

If you are one and he’s the other, it could present some difficulties if you have a relationship. The morning person wants to start the day early and go to sleep early, and that doesn’t fit in well if you’re a night person. Study results published in WebMD say that night owls tend to drink more caffeine and alcohol, but they can stay more focused during the day than early risers. Morning people tend to sleep better and feel healthier.

10. Are there any foods you don’t eat?

Although food preferences generally don’t make or break a relationship, if your date eats differently from you, there could be some problems. For example, if you’re a vegetarian and he’s a meat eater, you two are probably incompatible, particularly if you don’t eat meat because of your religious or other beliefs.

11. Do you have a nickname?

If he does, then you get to hear the story behind it. If he doesn’t and you do, you can tell him the story of your nickname. If neither of you has a nickname, you can talk about the funniest ones you remember your childhood friends having.

12. Were you popular in high school?

You can find out what type of person he was in school by asking this question. You’ll find out whether he played sports, cut classes, or got good grades. There are probably many stories he could tell you about high school, and you can share some of your own, making this a good first date question.

13. If your house caught on fire, what would you be sure to save?

This question lets you know what he treasures or finds important. Maybe he’ll say something practical, like his wallet and phone. Or maybe he’ll save his pet. Some people would save special keepsakes, and those usually have a story behind them. Maybe he has some treasured artwork. And a bonus to asking this question is that you both will be prepared by now knowing exactly what you’d take if you really did have a fire at home.

14. What are you afraid of?

This question lets him show that he has a vulnerable side. He might not like heights, rats, spiders, or public speaking. Or he may have a fear that surprises you. If he can’t think of anything (or doesn’t want to say), you go first. After he hears what you’re afraid of, he might then answer you.

Meanwhile, you might want to ask yourself some questions – like whether you want to have sex on the first date.

The first date questions we suggested should help you have a smooth, fun first date. But you also must realize that not every date, no matter how hard you try, will result in chemistry between the two of you, even if you have asked all the right questions. Give your first date a chance, though. Asking the right questions could very well help make your first date a great one.

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