The Best Questions to Ask When You’re on a First Date

A first date can be nerve-wracking. You’re worried about your clothes, your hair, and what you’ll say to your date. You want to sound witty and interesting, but you also don’t want to look like you’re trying too hard either. It can be hard to think of questions to ask when you’re filled with nerves. However, with a little preparation, you can carry on a first-date conversation with ease and grace. Asking the right questions can help you learn more about your date and help both of you get a little more comfortable with each other. Here are a few tips for the first date as well as starter questions that will help you get to know each other better.

a couple on a first date

Now’s your chance, make a great first impression! | iStock.com

Relax: You want to gain some insight, but you should also remember to have fun. You don’t want your date to feel like an interrogation. Make sure to ask some fun questions. Every query doesn’t have to be very serious or probing. And you don’t want to probe too much when you’ve just met. Being overly suspicious and defensive will likely be off-putting to your date.

Be polite: Don’ talk over your date. Give each other time to respond to questions, and don’t turn every comment into a debate. If you like to argue, join a debate club.

Maintain eye contact: Eye contact is not only sexy but also shows that you’re listening and engaged. If you’re shy or nervous, take a moment to look away every now and then, but always come back to meet your date’s eyes. And if you’re feeling bold, focus on their lips once in a while.

1. What are some of your hobbies?

waiter serving wine to couple

Do they love to hike? Or are they more of an indoor person? | iStock.com

This will help you see what things your date finds fun and interesting. Your date may spend a lot of time on these hobbies, and if you get serious, may want to involve you in these activities.

2. How did you choose your career?

Students Training To Work In Catering Industry

Did they end up where they are intentionally or by accident? | iStock.com/bowdenimages

Most people have interesting stories to tell about how they landed on their chosen career path. A discussion about careers may help you learn more about their motivations and work ethic.

3. What are you most passionate about?

man and woman holding hands while crossing the creek

It’s always interesting to learn what makes someone else tick. | iStock.com/jacoblund

Your date’s passion will be where much of his or her time and energy is spent.

4. What are some of the goals on your bucket list?

woman in airport doing self check-in

This one will be a huge conversation starter. | iStock.com/encrier

This can provide some insight into areas of your date’s life that have yet to be explored.

5. How long ago was your last serious relationship?

Grabbing a beer on a date

Do you have a serial dater on your hands? | iStock.com

The timing may show you whether your date is ready to begin another relationship. If it was very recent, you may want to explore why he or she is dating so soon.

6. What was the reason your last relationship didn’t work out?

Broken heart hanging

Ask this question with caution. | iStock.com/grafvision

Also ask who initiated the break-up and why. This may give you some insight into how he or she handles conflict and what they find important in a relationship. In addition, how was the news delivered? If your future partner says it was via text, email, or worse — social media — you may want to proceed with caution. Someone that insensitive will likely treat you the same.

7. What’s your biggest relationship regret?

Heart shaped hands

Above all, have fun and make sure you listen! | iStock.com

Did he or she wish they spent more time with their ex? Did they fight all the time? Ask what your date would have done differently.