The Best Icebreaker Questions for First Dates

By Margaret, 04 May, 2023.

The Best Icebreaker Questions for First Dates

April 12, 2023

You’ve mustered the courage to head out to your first date, you’ve put in a lot of effort getting ready and looking nice, you get to the restaurant and you greet your date. Now you’re sitting down and you’ve asked them how they are and all of a sudden the conversation goes quiet and you’re desperately trying to think of something to say. Instead, all you can think of is how badly this date is going.

We’ve all been there. It’s easy to get caught up in your thoughts when these situations arrive. Starting up a conversation with someone you have met for the first time can be daunting. You get the urge to break the silence by saying something, anything..literally anything.

Remember, they are feeling the same

If you have been sitting there in silence, it’s not just you who’s feeling awkward, you’re both in this together so it’s ok to admit that you are nervous. It will not make them run off. You both agreed to go on a date to learn more about each other and the questions you ask them will help you do just that. Here are some questions you could ask to get the conversation started.

Understanding what they do for a living.

Career-based questions are a good way to get an insight into what a person does and most importantly, what they want to do. Generally, the person you’re on a date with does not want to talk about work because it is what they have been doing the entire week. However, asking about their ambitions really lets them start thinking about what they want to achieve.

Would you rather have unlimited money or have a dream job?

What is your dream job?

What is the worst job you’ve had?


Learn about their character.

Once your conversation has started to have a bit of a flow you could lean into asking personal questions. Often, learning about a person’s younger self gives you an insight into their character and how they have changed.

Tell me the most embarrassing teen year moment?

What is a big lesson you learnt in your younger days that you still remember?

If you could go back in time to when you were a teenager, what advice would you give yourself?


Life experiences

Back-to-back questions may start making your date feel more like an interview. It may be time to switch up your question. Asking questions that allow the other person to think about a good memory is a nice way to make them feel more relaxed and helps to take them to their “happy place”.

What is the best place you went for a holiday?


If you could go anywhere for a holiday, where would you go?


Daily routine

If you are enjoying the company of your date, you may start imagining what they are like to be around on a daily basis. Asking “Are you a fun person to be around?” may feel a little too on the nose. Instead, try understanding what their daily routine is like.

What is something you do regularly?

How do you unwind after a big day?

Tell me about your daily routine.


We believe that any experience you have during a date, good or bad, still helps you get more comfortable being around people. Not being afraid to ask questions is also a skill that could help you in your daily life. Many of us forget how to interact with a person in a one-on-one situation and it is important to remember that if you are feeling awkward, chances are that the other person feels the same. It is important to keep an open mind and allow the other person to express how they feel without judgment.

Let us know if these questions have helped you get past the “awkward stage” of your dates!