7 Ice Breaker Questions That Really Work

First Date Young Adults Having Coffee - Awkward Silent

Why is it important to go on a first date with some good ice breaker questions in the wings?

Imagine being on a first date with someone you do not know very well. You really like this person based on their online dating profile and your goal during this time is to make a great impression that leads to a second date. You are thrilled to be here but also a bit nervous and uncertain of what might unfold during this time.

The date could be going really well. You are saying all the right things. She or he is responding in ways that show you two have good chemistry. The relationship seems simpatico. But then you get to a point in the conversation where there is an awkward silence, and you are left wondering what to say to fill the void. Your mind begins to race. You desperately look for something that will bridge this weird gap! But you find nothing.

Awkward silence in a conversation is quite typical for a first date and certainly not the end of the world or the relationship! So do not beat yourself up too much if it does happen. But awkward silence is never ideal. Ensure that you never draw a blank again in front of your date and check out our 7 best ice breaker questions that work well!

#1: Do You Want To Hear the Story of Why I Responded to Your Online Dating Profile?

People love hearing about what makes them unique from others. It is a topic of conversation where you can never really go wrong. The key here is not to go for over-the-top flattery, but the simple truth of what made this person stand out to you.

This is a great way to break the ice on the first date and it shows your date that there was something special about them that really made them stand out from the other dating profiles you viewed. It can be a great opportunity to give them a genuine, sincere compliment and, at the same time, make them feel truly appreciated. It can also reveal that you chose them for a special reason, and it was not simply based on their looks, their availability, or any other superficial convenience.

If you are feeling extra bold (and, let’s be honest, you are fishing around for a compliment), you can turn the question around and ask your date what it was that made you stand out. If their response is sarcastic, this can be a great opportunity for some light self-deprecation that shows you have humor but a ton of confidence.

Using this ice breaker question can lead to some interesting stories that are sure to keep the conversation flowing at a natural pace! As long as you are honest and sincere, this can lead to some top-shelf relationship building that will definitely score you another date.

#2: What Does Your Perfect Day Look Like?

For many, perfect days are few and far between. When they do occur, they are special and sacred. It is not uncommon for people to daydream about their perfect day scenario. A day without any worries. A day that goes smoothly and is free of conflicts from friends, family, or work. A day where life can be lived to its fullest and the pleasures of life abound.

Ok. We are getting a little too poetic there, but we think you get the point.

One of the best reasons to ask your date about what makes their perfect day is because it will put them in a positive state of mind. When you begin thinking about your perfect day scenario, you can’t help but have a sunnier outlook or go to a place in your head where you feel relaxed and pleasant. In turn, this can help the date to move along at a pleasurable clip.

There is also a great ulterior motive for you in asking your date this ice breaker question the first time you get together. And when we say ulterior motive, we are not implying anything devious. On the contrary, getting information on your date’s perfect day is something you can store on file for a later date. Now that you know what their perfect day entails, you can make it happen for them!

#3: What Is Your Greatest Achievement or Proudest Accomplishment?

Asking your date about their greatest achievement or proudest accomplishment is a good way to find out more about what makes them tick. It can reveal to you what they value and what kind of goals or standards they have set for themselves.

There are definitely people out there who can answer this question without much thought, but for many, this question is usually one that requires some careful consideration. But it does seem that most people are interested in answering this question given they have some time to think about it.

This is a question that is typically asked in job interviews so you might want to reword the question a little bit, so it comes across in a more naturalistic way. After all, you are on a first date and not hiring someone to be the head of your HR department.

You might be able to introduce this ice breaker question into the discussion more creatively if you first tell them about something you have accomplished that you take a lot of pride in and cap it off with, “that is probably one of my proudest achievements of all time.” You could then ask, “what about you?”

#4: What Is the Most Spontaneous Thing You Have Ever Done?

This is one of the best questions to ask on a first date and it will give you an opportunity to see the wild side of your date. Stories about spontaneous things you have done in the past are always fun to tell and this will allow you some time to sit back and actively listen while your date recounts a time when they were feeling impulsive or daring!

One thing is for certain. Sharing stories like this can lead to some great laughs in the moment, but they can be a great source of material that you can call back to when you want to make your date laugh in the future. Always be listening, observing, and learning everything you can about your date. Crazy stories are always a surefire method for keeping the date fun and exciting.

Another great reason to ask this icebreaker question is to gauge how spontaneous your date can be. If they enjoy being spontaneous or enjoy acts of spontaneity on your part, this can lead to some awesome future date or gift ideas! Maybe you will go skydiving next time you get together. You could surprise them with tickets to a show they have been talking about. Or maybe you could both go on an impromptu road trip.

#5: What’s Some of the Best Advice You Have Ever Received?

If you and your date begin discussing more serious matters like hard experiences that have taught you life lessons or overcoming personal obstacles with some help from a friend or family member, this might be the perfect ice breaker question to pull out if you sense an awkward silence coming in the conversation.

Asking a question like this can give you some insight into your date’s character and how they function when faced with a challenge. It can even reveal how well they receive feedback or constructive criticism. Remember, the date is a chance to build the relationship and part of that work is understanding your date and what makes them tick.

It is always good to be as transparent with your date as they are with you, so feel free to share some good advice that you might have gotten over the years from someone you trust or respect. This ice breaker question can also lead to potential conversations down the road about important people in each of your lives. That good advice came from someone, after all.

#6: How Did You Meet Your Best Friend? What Makes You Two Get Along So Well?

If the conversation turns toward your date’s friends, this can be a great chance to find out what kind of person he or she typically enjoys hanging out with. And if you are anything like their friends, your chances of getting closer to your date and developing a quality relationship are going to be off the charts!

People like talking about their friends and origin stories surrounding friendships can stir up feelings of nostalgia or happy remembrance. Like the earlier question about your date’s perfect day, this ice breaker question is one that can instantly put your date in a positive, happy state of mind!

The follow-up question “what makes you two get along so well?” is a good one to ask because your date has to admit what it is that makes them compatible with that friend. This can allow you to gauge what it takes to be compatible with your date going forward!

#7: Do You Have a Reoccurring Dream?

This is an ice breaker question that has a little bit of risk involved and could possibly lead to a dead end in the conversation. But with the right person, this question could prove to be a little goldmine when it comes to the quality and volume of conversation!

Even if you are a person who does not have dreams on a regular basis, it is always interesting to hear about other people’s dreams. It could turn into a fun game with your date where you try to figure out what they mean! Chances are that, between the two of you, one of you has had an interesting dream recently so it doesn’t hurt to go out on a limb and ask this one on a first date.

What Do We Mean by This?

Well, not all people have dreams, at least dreams that they remember clearly and can recall the next day. However, there are people out there who dream every night and love telling others about their dreams! If this person is your date, this is an ice breaker question that will undoubtedly spark a quality conversation and it could snowball into being the main point of discussion for the date!

Matt Marino
Matt Marino

Matt Marino is an online content writer for DatingApps.com, specializing in trending blogs and dating app reviews. He is a graduate of Geneva College with a Bachelor of the Arts in Communications.