Ice Breakers For Dating: 10 Questions You Should Definitely Try

Tips to increase the chances of hitting it off with your date

Hily Dating App
Sep 1, 2020 · 4 min read

First dates can be boring as hell, fun, or just “meh.” However, there’s one thing they have in common: they are usually pretty awkward and nerve-wracking. The pressure we feel about leaving a good impression on our date can completely ruin our chances of hitting it off. We may come across as boring, uninterested, or stuck up. That said, we wanted to teach you how to become the master of dates by sharing ten ice breaker questions you should try on your next date.

Photo by Giorgio Trovato on Unsplash

Question 1: Tell me some random facts about you.

Let’s face it. First dates may be uncomfortable. If you want to avoid the awkward silence with your date, you might ask them to share some random facts about themselves.

This question will allow you to get to know your date better and offer a good starting point for a more easy-flowing conversation. Besides, by sharing something your match might usually avoid, you’ll get a better look into their personality.

Question 2: What’s one unpopular opinion you share?

“Breaking Bad is overrated” or “Pineapple works on pizza” are just some opinions people around the globe share. Asking this question on a first date can help you break the ice, as your date will probably be passionate about explaining why a certain opinion means so much to them. It’s an excellent way to make an engaging conversation from the start, making the atmosphere more relaxed.

Question 3: Tell me one thing that annoys you the most?

Loud chewers, or people who take an eternity to respond to a message? We all have something that annoys us.

If you want to get to know your date better, you might try to ask them this question. You may even find you’re annoyed at the same things!

Question 4: If you could turn back time, what would you change?

As Cher sang in one of her songs, if she could turn back time, she would undo the things she said and make it right.

Everyone has regrets. Every mistake we make teaches us valuable lessons. By asking this question, you’ll be able to stir the conversation but also get useful insights onto your date’s personality, their view on life, and create stronger bonds during the date.

Question 5: If you could switch places with a celebrity, which one would you be?

Finding the right partner means finding a best friend and a lover in the same person. This question might help you gauge your date’s ability to imagine and relax, which can be beneficial in the later stages of the relationship.

Question 6: What’s your guilty pleasure?

Trashy music, or junk food? Everyone has guilty pleasures. This question can help you start a conversation playfully. It can also be a good sharing point, as you have your share of guilty pleasures for sure.

Question 7: How did you choose this profession?

The job we do makes a significant part of our lives. It’s where we spend most of our days and a place that impacts our overall life satisfaction.

By asking this question on a date, you’ll be able to get valuable insights into your date’s personality, passions they have, and what they expect from life.

Question 8: What’s your childhood’s happiest memory?

Understanding where your date is coming from can help you both connect on a deeper level. By asking this question, you’ll get a glimpse of how they were brought up and what values they share. It can also help you connect with them on a deeper level, as they will share with you deeply personal memories, not visible to the naked eye.

Question 9: Tell me something embarrassing about yourself?

Somebody caught you singing loudly in your car? People saw you talking to your pet as if it was a person? So what! We’re sure your date has something embarrassing about themselves to share as well!

If you want to start a conversation on a lighter note, you might want to ask your date this question. Laughing together is one sure way to connect with others.

Question 10: Do you think money can buy happiness?

Money talks could be a bit too much for the first dates; however, seeing your date’s view on money could be beneficial. It can give you a better insight into whether you share the same opinion and be a good heated-discussion starter.

Do you feel more ready to rock your first date?

Many of us feel nervous about our first dates. Maybe we take them too seriously, or perhaps we’re too afraid of judgment. But we shouldn’t. There's a possibility your date will become the person we will fall in love with. These questions can help you be more honest, exciting, and playful, pushing away the awkwardness of first dates once and for all.

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