First dates can be daunting, especially if you have been out of the dating scene for a while. It’s normal to feel anxious or apprehensive about what questions to ask and how to approach the first date after so long. However, it’s worth remembering that the person sitting opposite you will likely be having similar feelings.

Knowing what dating questions to ask can break the ice and allow the conversation to flow naturally. Part of our work as matchmakers is to provide personal and tailored introductions for single men and women across the world.

We work with you to identify exceptional individuals who share your core morals and long-term relationship goals. This also involves helping you overcome any dating anxieties and understanding what kind of questions to ask on a first date.


The Easy Ice Breaker Questions for Dating Again

For first dates, you don’t want to lead with anything too personal or severe. Choosing an appropriate date location and keeping the conversation light and fun are the two key points you want to meet.

These icebreaker questions cover two core areas: their work and their hobbies and interests.

Their approach and attitude to their work and career

This may seem like a safe opening question but that’s exactly what you want at this stage. Employment is an easy and neutral topic of conversation, one you will both be able to empathize with. Work-related questions will also shed light on the type of person you’re sitting opposite. Learning about someone’s work and their attitude towards their career can offer a good insight into personality traits; are they career-driven? Do they enjoy their employment? Do they work too much? These questions and attributes will help you form a better understanding of their personality and even paint a picture of the type of relationship you might have with them.

Some work-related questions might include:

  • Where do you work? Do you enjoy your role?
  • What are the best and worst things about your job?
  • Have you made any close friends at work?
  • Are you more of an early bird to work or the last one in?
  • When work ends, how do you typically spend your evenings and weekends?

The last question is important, as it offers a natural springboard onto other conversation topics, like their hobbies, what TV shows they enjoy, if they cook and other pastimes.

Discovering their hobbies and interests

Jumping from work to hobbies is usually an easy transition because you should be able to glean their basic interests from how much or little they enjoy their career. Work and hobbies are two vitally important conversation topics to cover on a first date as we spend most of our lives finding a balance between the two. How the person sitting opposite you chooses to spend their time will help outline the things most important to them.

Some questions you may want to ask that will uncover more about their hobbies and interests might include:

  • How would you spend your ideal day off?
  • What are some of your favorite activities or interests?
  • What does a typical weekend look like for you?
  • If you could become a master of something, what would it be and why?
  • What’s one thing you wish you could spend more time doing?

There’s a reason why dating questions typically revolve around hobbies and that’s because learning about your date’s interests will help you figure out whether they align with your own and how you’d spend time together if they didn’t.

If you find you don’t have too much in common, this doesn’t necessarily mean you both go your separate ways. Instead, consider if you would be willing to try out their hobbies or vice versa. You may discover a new side of yourself that you would not have otherwise!

Broaching the ‘Really Getting to Know You’ Questions

We generally advise against deeper, more personal or even touchy questions on a first date but some can be asked on a first date if the moment and feels right – but make sure you’ve covered the bases of their work and interests before moving on to more in-depth ‘getting to know you’ questions.

For the most part, we go on dates in search of a partner whose interests and long-term relationship goals align with our own. We want to find a partner who we can spend the rest of our lives with. Of course, we don’t expect you to know whether or not your date for the evening is ‘the one’ during drinks or dinner but you can ask questions that will give you a good indication of whether or not this person’s life ambitions match up with your own.

Again, be mindful of asking these questions too soon as you might come across as too serious or “too intense”. Remember, first dates are all about leading with icebreaker questions and enjoying each other’s company. Only when you feel comfortable should you ask questions relating to their relationship visions for the future.

  • Where do you want to be in 10 years? What does your life look like?
  • Are you the type of person who is looking to settle down soon? Or does this not appeal to you?
  • What are your thoughts on having children when you’re ready?
  • Are you looking for a serious relationship or are you still casually dating?

You may be thinking these questions are too intense for a first date and that’s okay. You should be able to tell whether or not these questions are appropriate to raise during the first few hours, if not, you can always ask these dating questions on your second or third date.

If you’re looking for more advice on how to find the right person, there are 9 additional factors you might want to consider.

When Was the Last Time You Went on a Date?

For some people, dating remains a daunting prospect, especially for those who have either recently come out of a long-term relationship or those who struggle with confidence. The good news is that these are common problems that can be easily addressed with the right approach.

As well as specializing in psychology-based matchmaking, we also provide a dedicated date coaching service for those who want to feel more in control of their love life. Our expert date coaches have helped hundreds of single men and women uncover what might be getting in the way of finding their ideal partner.

Whether you’re currently single and feel trapped or misunderstood or you’re in a struggling relationship that you want to make better, our date coaches can provide specialized support to address these issues.

To learn more about our date coaching process or if you’re looking to meet exceptional single people in the US or farther abroad, please get in touch and we will get back to you.