Top 15 First Date Questions

Top 15 First Date Questions

Your first date with somebody new can be a very exciting experience. There’s all sorts of electricity, flirtatious energy, not to mention usually a strong physical attraction between you and the other person. What’s more, the first date could well be the first step towards building a lasting and meaningful relationship.

One key problem stands in your way, however. What to talk about during the first date. You want the conversation to flow naturally, and it might do, but it’s always best to be ready with some great backup questions that you can turn to, just in case nerves are getting the best of either of you during the date.

Best 15 Questions to Ask on a First Date

1. Tell Me More About Yourself

Alright, this one seems a little cliche or perhaps even a little boring, but it’s a solid, easygoing, and effective ice-breaking question. Why? It doesn’t ask anything too specific, which leaves your date with plenty of room to offer up information that they are comfortable sharing at this stage. When you ask questions that are overly specific, you increase the chances of things becoming awkward. So, start with something nice and simple.

2. What Did You Do Last Weekend?

This is another great example of an open-ended ice-breaking question. It seems specific when it asks about last weekend, but don’t forget that the weekend runs from Friday night to Sunday, so there’s plenty for your date to choose from. It’s also a very easy way to gain some immediate insight into what your date enjoys doing in their free time. You might quickly learn that you share a hobby or interest, which then leads to a rich vein of subsequent questions and discussion topics.

3. Do You Like Your Job?

By the time you’re on a date with someone, you might already know what it is they do for a living, but you’ve likely not talked at length about how much (or little) they like that job. Once again, this can be a great insight into the mindset and lifestyle of your date. If they are in a dead-end job that they hate, maybe they have ambitions to change that, or perhaps they love their career, so you know that this is something they care about. In all cases, you learn valuable things about the other person.

4. Where Did You Grow Up?

Another classic and common question, but also a great way to open up another rich vein of potential follow-ups. You might come from the same place, or places close together. You might have another connection to your date’s hometown, such as you attending college there, for instance. It’s a nice, safe, ice-breaker that offers much potential for reciprocation and follow-up.

5. Are You From a Big Family?

Whether your date answers yes or no to this question should trigger some interesting follow up and conversation. If they respond with “yes, I’m the oldest of 8 siblings,” then you have a lot of scope to ask about and learn about their family. You can also offer up your own stories. Even if they’re an only child and don’t have much family to talk about, something like the pros and cons of having siblings still makes for a pretty engaging topic on a date.

6. What Makes You Unique?

This may on the surface sound a bit like a job interview question, but in the context of a date, it’s actually quite romantic, and offers great potential for learning about another side of your date’s personality. Whatever answer they give and whatever your reaction to it will greatly inform you on whether you and this person have potential. They may respond with something rather humble and sweet, in which case your feelings for them might grow. Alternatively, they could say something rather narcissistic, letting you see early on that you might not be a great match.

7. What is a Random Fun Fact About You?

A question like this is basically an invitation for your date to tell a funny anecdote about their lives so far. It could be something both interesting and impressive like “I’ve worked on five continents,” or “I speak 20 languages.” It could also be something very endearing like “until tonight, I’ve never been on a single fun date.” In short, it’s a great way to share interesting and fun things about each other, thus deepening your connection.

8. Would You Rather…?

A “would you rather…” hypothetical question can also be a fun little conversation starter. You could base it on the film you watched before dinner, or on another scenario that connects the humor and rapport you’ve established on the date so far, or something else. Try not to make it too vulgar or personal, and you’ll most likely create a fun topic of discussion that could go on for some time and generate a few ice-breaking laughs along the way.

9. What’s Your Biggest Pet Peeve?

There are some who might balk at this question being asked on a first date, thinking that it just sounds so negative. Yes, discussing pet peeves means revealing things that we hate, but it’s an exception to the general rule of “no negativity” because it’s a topic that invariably leads to humorous sharing of things that we actually all agree are annoying. Everyone has at least one pet peeve, and many of them we do share in common. It can actually be a very unifying topic.

10. What’s the Most Embarrassing Thing to Happen to You On a Date?

This is a good one to ask a bit later in the date when the atmosphere has become a bit more relaxed overall. Much like the “would you rather…” and “random fun fact” questions, they invite you both to share amusing anecdotes that help not only to ease the tension of the first date, but also to humanize you both in each other’s eyes. When that happens, it becomes easier and more relaxed to be in that situation, and you can feel more at ease talking about other things.

11. Where is Your Favorite Place in Town? Or in the World?

To inject some positivity into your conversation, why not ask your date about places they genuinely love. These can range from local spots they visit frequently, to far-flung places around the world that they have traveled to or hope to visit. We all have places that we love that make us feel comfortable and fuel our happy memories. Why not share them in conversation?

12. Where Do You See Yourself in 5 Years?

This is another one that’s a bit like a job interview question, but once again it’s all about setting the context. You might ask it in a professional context as a follow up to the question about whether they like their job or not. On the other hand, you could ask it more generally about life, including their personal life as simply a way of asking them about their hopes, dreams and aspirations.

13. Do You Have a Bucket List?

This is a nice and simple way of asking your date about things that they want to do or achieve in life. It’s a great question because it gives you insight into what you and this person might spend your time doing together if this dating regime turns into a more serious relationship later on. For instance, if your date reveals that bungee-jumping, or climbing Mount Everest is on their bucket list, you might wonder how or when you could factor into those activities.

14. Where Was Your Last Vacation?

People love sharing stories about their travels and vacations, no matter where they had the vacation. It could be Atlantic City, it could be a luxury villa in the Maldives, it makes little difference in principle. It’s a nice way to learn about what makes your date happy, relaxed and content. If you plan to surprise them with a trip in future, you’ll know what kind of places they like.

15. Would You Like to Do This Again Sometime Soon?

Finally, you can’t finish a great first date without asking this question. If it didn’t go well for you, then you can leave it off the roster, but when it does go well, it’s a must. Their positive response tells you that you’re onto something potentially great here, but if they say no, then you’ve avoided getting in too deep and getting hurt.