7 Ice-Breaker Questions to Ask during First Dates

Shayma Popova
3 min readJul 12, 2022

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First dates can either be exciting or nerve-wracking, awkward or fun, disastrous or memorable, among other things. One factor contributing to the pressure is the first impression you leave and how well you connect with your date.

One rule of thumb is to avoid topics like politics and religion. This is to keep your date light-hearted and cheerful.

So what are the things you can discuss to ensure a free-flowing conversation? Here are some good examples.

1. “What makes you stand out?”

Encouraging people to talk about themselves is a good way to connect with them. You can ask about their interests, hobbies, or passions.

Do they enjoy dancing? Reading? Going out? Painting? Or sports?

This also makes it easier to see if you have any common interests. And if the date goes well, it won’t be that hard to plan for a second one.

2. “Do you have any good jokes?”

You’ll quickly get an overview of a person’s sense of humor if they share a joke that made you laugh.

Likewise, laughing at each other’s jokes is another way to break the ice during your first date, making the two of you feel comfortable.

3. “What’s your most embarrassing experience?”

Try to see if they’re fine with talking about some of their most embarrassing experiences.

Many believe that being able to talk about these moments can be a good way to showcase your sense of humor, vulnerability, and humility. That’s because it’s not something that you freely talk about with anyone else.

4. “Who do you consider special in your life?”

You can encourage your date to talk about their family, friends, or pets. Be mindful of how they talk about these people to learn more about their character.

With this topic, you can also tell which people have had the biggest impact on their life and who has helped shape them into who they are today.

More importantly, this kind of conversation can be insightful. You might notice their eyes sparkle when they talk about the people they look up to.

5. “What are you proud of?”

You can ask about their greatest achievements or favorite moments in life.

It’ll help you determine some of the experiences they value and the things they’ve put their blood and sweat into.

6. “What’s your favorite place in the world?”

You can ask questions like:

  • Do you have a secret place you can go to unwind?
  • Do you know of a hidden hiking trail?
  • Do you have a favorite vacation destination?

These questions will give you an idea of what type of setting makes them feel safe, happy, and comfortable.

7. “What’s your biggest pet peeve?”

Don’t be afraid to talk about the things that get on your nerves. Asking this question will show whether your date is laid-back or gets easily stressed out.

It’ll also be a way for you to be open with each other right from the start.

Find the Right Conversation Starters

Nothing is more nerve-wracking than first dates, especially with someone you’re meeting for the first time.

Dates are designed to build the foundation for a relationship.

Then again, some first dates can be like casual interviews disguised as social encounters, which is why you need to determine what to talk about beforehand.

Remember that finding a partner doesn’t come from the checklists in your head. It’s more about the connections you establish when you actually get to know someone in person.

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Shayma Popova
Shayma Popova

Written by Shayma Popova

I write truths about dating and relationships as a Content Manager for https://odessawomen.com/

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