Picture this: you’re on your first date with a person and you really feel you two could hit it off. After some small talk, you’re both sitting there awkwardly, hopelessly looking for the right words to keep the atmosphere alive. So, how do you keep a conversation going on a date?
If you’re truly a match made in heaven, you won’t have trouble finding common ground, but sometimes you need to ask the right questions and get to know the person before you’re both relaxed enough to open up.
If you’re worried your mind will freeze, and you’ll run out of topics, there’s no harm in doing some mental preparation and stocking up on ideas to ask your date. Here’s a list of questions to get you going, so dig in!
What to Ask on a First Date: Breaking the Ice
You’ve talked about the weather, the horrible traffic, commented how the café is lovely, and now you’re sipping your drinks and waiting for the other person to pick it up from there.
Now is the time to start asking questions that will inspire casual conversation. Of course, you don’t want to make it sound like an interrogation—aim to make the questions natural and appropriate for the current “vibe” that’s between the two of you.
Considering that you’re both probably excited, nervous, and don’t know what to expect, it’s nice to have a few aces up your sleeve. So, without further ado, here are things to ask on a first date.
Ask them about their day/week.
A good tip is to start with easy questions that reveal a bit more about your date. They’ll get the impression you’re genuinely interested and be more confident to tell you their story.
Asking about their day may seem weird because you’ve never seen them before, but it’s a topic that doesn’t require a lot of brainstorming, and it’s still fresh for both of you. It also opens up the path to other topics and questions. Here are some specific examples:
- Did you have a busy day?
- Did you do anything fun this week?
- What do you usually do at this time of the day?
- Are you planning anything for the weekend? (if it’s a work day or a Friday night)
- What’s your typical day?
Ask what they do.
Work-related questions are typical conversation starters for dating. Our career dictates our lifestyle, and you can learn more about the other person’s goals and ambitions. Don’t go overboard with this topic, though, because it can bore and put off your date. Here’s what to ask:
- Where do you work?
- Is this your first job?
- What do you like/dislike about your job?
- Do you want to take a different career path?
- How do you get along with your coworkers?
- What are your ambitions?
- What’s something you’re good at?
If your date is unemployed or reluctant to talk about their job, you can ask about the school/university they attended. That way, you can find out if you have common acquaintances or friends, which opens up new conversation topics.
Get to know their personality.
Personality questions are great questions to ask on a first date. Still, dating experts recommend talking about specific situations and scenarios rather than firing dull what-is-your-favorite questions at them. Good examples include:
- Are you introverted or extroverted?
- What do you like to do for relaxation?
- Do you exercise?
- Do you prefer active or laid-back vacations?
- What do you think is the most interesting thing about you?
- Are you a cat or a dog person?
- What are your hobbies/talents?
- Do you speak any foreign languages?
- Are you a morning person or a night owl?
- Do you prefer watching movies at home or at the cinema?
- What are your pet peeves?
These and other similar examples are excellent date questions to get to know someone. You might hear some interesting stories about your date, and they’ll invite you to talk more about yourself in return. Who knows — you might have more similarities than you initially thought!
Ask about their upbringing.
When the present offers no more material, it’s time for a blast from the past. You can ask about their school years, childhood memories, or their hometown. If you notice your date is uncomfortable with these questions, switch to lighter topics.
Here are some great first–date questions you can ask about your date’s upbringing:
- What were you like as a kid?
- Do you have any siblings?
- How would you describe your family?
- Do you have a big extended family?
- Do you visit your hometown often?
- What’s your happiest/most embarrassing childhood memory?
- What were you like in high school?
- Do you still hang out with your childhood friends?
- What’s the best part of your childhood?
Fun Dating Questions
Now that you’re both more open and relaxed, you can shift to other topics and have some fun. Let’s see some creative first–date questions to ask and spice up your date.
Focus on their interests.
Books, music, movies, TV shows — pop culture is a rich source of information that will spark lively conversations. Explore their hobbies, likes, and dislikes to find commonalities and maybe even get an idea of what to do on a second date (if there’s potential for it).
Some suggestions are:
- What was the last show you binge-watched?
- What’s the last thing you read?
- Are you into fitness/sports?
- What’s a song you’ll never get tired of listening to?
- What’s the best destination you’ve visited?
- Where would you go if you could pick any place on Earth?
- What was the first band you listened to?
A bonus tip is to recall some movies, songs, and TV shows that marked your childhood and take a trip down memory lane.
Get a little philosophical.
Good first–date questions also involve hypothetical questions that spark discussions and let your imagination run wild. Propose some fun scenarios and ask your date about their wants and desires. For instance:
- What would be your superpower if you could choose any?
- If you could pick a theme song to play when you’re walking down the street, what would it be?
- You can get an infinite supply of one item for the rest of your life — which item is it?
- What would you take on a desert island?
- If you could do something for the first time again, what would you do?
- What are some things on your bucket list?
- What’s the best advice someone gave you and why?
Get flirty.
By now, you’ve had a couple of drinks and broken the ice, so there’s no harm in a little flirting — within boundaries, of course. Here’s a list of flirty and romantic questions to ask on a first date:
- What’s the best part of dating you?
- If we went on a second date, where would we go?
- What’s the weirdest place someone took you out on a date?
- How do you imagine a perfect date?
- What’s your favorite thing you’ve learned about me on this date?
If you notice you’re making your date uncomfortable, steer clear of openly sexual questions — you’ll have time to explore your sexual side on one of your following dates. In turn, these questions allow you to flirt and compliment each other, which works in your favor.
What not to Ask on a First Date
While asking on-point questions will increase the prospects of a second date, you don’t want the other person to feel like they’re on a job interview. Some questions can cause your date to misinterpret your intentions or make you sound arrogant and selfish.
Let’s go through some questions to avoid on a first date:
- I think you’re amazing, how are you single?
- Do you think we have a future together?
- Are you seeing other people?
- Are you good with children?
- How do you get along with your parents?
- Are you on dating apps?
- Why did you break up with your ex?
- How many people have you slept with?
- What’s your favorite sex position?
These are the best questions to ask on a first date if you want to make sure you’ll never see them again. Asking them about their dating and sexual history or implying you’re serious about them after one date can be overwhelming.
Giving your date space to process and decide if they want to keep dating you is the best way to go. In addition, good manners, not being too personal, and not trying to pressure your date into liking you will get you a long way.
Bottom Line
First dates are always exciting and decisive. If the two of you turn out to be compatible, the chances of a second date or something more are very high.
Knowing what to ask on a first date can help ensure the other person will stay interested in you, but it can also determine whether you’re a good fit and whether you should keep dating.
We hope this guide has given you food for thought. You can always mix and match, and modify the questions so they come out as natural as possible. If you play your cards right and the date goes smoothly, you might be lucky enough to have found the right match!