Breaking the ice: 10 questions to ask on a first date


First dates don’t always run smoothly. It’s easy to become nervous, self-conscious, and overthink the entire situation leading to a dating disaster. While one wants to determine compatibility, it’s not always easy to do so without making it sound like a grand inquisition. Dating should be fun, easy going and exciting. It doesn’t take too long to figure out whether the conversation is on par with pulling teeth, or flows as though you’ve known one another forever. The best preparation is in finding questions that will give insight into one another’s lives, while also bringing about flirtation, laughter and an overall good time! Not sure where to begin? Here are ten questions for breaking the ice on a first date!

1.What do you miss about childhood?

Often people reminisce about childhood, and have fond memories of what it was like to be young. Asking about your date’s childhood will help paint a picture into what activities they were into, what type of person they are, and even what their family life was and is currently like.

2. What is the most embarrassing thing you’ve ever done?

It’s important to introduce some silliness on your date. It can’t be all questions and answers. Talking about most embarrassing moments will not only make you aware of some of the crazy things your date has done, but will also open a door to sharing funny stories which makes for great conversation.

3. Where is the most amazing place you’ve ever been?

Why wouldn’t one want to share the most beautiful, exciting place they’ve ever visited? This will not only give you an idea of whether they enjoy traveling, but it will also tell you if they are a beach lover, mountain climber, history buff ETC.

4. Do you like cooking or absolutely hate it?

When asked the right way, this can turn into a fun conversation about cooking disasters, or dreams of future home-cooked meals!

5. Where do you work, and do you enjoy what you’re doing?

It’s important not to give your date the idea that you are judging them based on their vocation, but it’s important to talk work. Do they like their job? Do they have dreams of doing something else, or are they content with where they work? Work is typically a big part of a person’s life, so it’s natural to care about what your date does for a living, and whether they are happy or frustrated with it most of the time.

6. If you could move anywhere in the world, where would it be?

Does your date dream of moving from New York to Florida? Find out where they dream of settling down, and most importantly, why!

7. Do you love animals? Any pets?

People love to talk about their pets, as well as their reasons for not having them. If you’re allergic to cats or dogs, and your date owns a pile of furry friends, it’s smart to get them talking about it from the start. The last thing one wants is to find out later in the relationship that they are sharing a bed with a puppy every night when it’s not something they are comfortable with. In addition, talking about pets often reveals a level of sensitivity.

8. Let’s talk shows. What series are you currently into?

It’s only a matter of time before you are fighting over the remote, cringing through programming you can’t stand. Get to talking about movies, shows, and anything television. You may find out you enjoy the same things, and have a long discussion about story plots and characters, or you may find out that this type of entertainment will never be an agreed upon part of life.

9. What is the absolute worst date you’ve ever been on?

Hopefully your date will not say “this one,” when asking this question! Most people have their fair share of dating blunders, and horror stories. What better way to break the ice than amusing one another with hilarious tales of failed love connections?!

10. What is your favorite pastime?

This is an essential question, and can be worded in many ways, but it’s always smart to determine if someone is a great match by talking about what they enjoy doing in their leisure time. If they adore camping, and hunting, and you’re more the hotel/vegetarian option type, it’s probably not a match made in heaven.

When going on a first date one hopes for witty banter, shared enjoyments, and mutual attraction, it’s not always easy to get the party started. Asking a mixture of funny, generally informative questions is the best way to learn the most about your new date while having an entertaining experience. Looking to bring your intimacy to the next level? Don’t hesitate, contact us!

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