top of page

7 Engaging Questions to Ask to When Dating with Intention

It's been years since you've been on the dating scene but after a long relationship hiatus, you've done the work and you're ready to get back in the game. Then bam, just like that you're on all these apps and have to start conversations with complete strangers. Where do you even start? I know, I feel you, it's scary - even for someone like myself who talks for a living. But it doesn't have to be a cringe-worthy task, I overcame my first date fright by looking at dating as an interview process for my heart. I mean, you're interviewing for the key to your golden city, you don't want just anyone taking that responsibility! Remember, you're the prize. They're interviewing for your heart just as much as you are for theirs. If you date with intention and ask the right questions, you're going to weed out the duds and find your person sooner than you think.

Asking the right questions can save you a lot of time, heartache, and most importantly, awkward pauses. It can quickly uncover whether you should run for the exit or run to order two more lattes to extend the date.

The right questions will help you...

  • Remove those awkward pauses and get the conversation started

  • Uncover whether you truly have a connection with someone or if it's just the caffeine boost...

  • Get to know the person on a deeper level through their history, personality, and sense of humour (that is important!) to better assess the compatibility of your potential partner

Are you ready for the secret sauce? Here are 7 questions you can use to get the most out of your first dating experience:

What does a day in the life of "insert their name here" look like?

I love starting off a date with this question because it gives an aerial view of a person's priorities and where they like to spend most of their time. Usually, this will include their career, their hobbies, and what they like to make for dinner (or if they eat dinner at all). It also allows me to assess if this is a lifestyle that I could get on board with in the future. Because let's be serious, I'm never going to say no to dinner...

What were you like as a kid?

You can learn a lot about a person by asking them what they were like as a child. You're able to learn about their family life, if they have siblings, and how they interacted with others. It could also spark them to share vulnerable parts of themselves that they feel comfortable enough to share with you. Learning about how they were as a child can lead to better understanding them as an adult.

What are you currently reading or listening to?

Books, music, and/or podcasts are a great way to find out what inspires and captivates a person. It signals they're interested in learning, has an imagination and a sense of creativity. You may find out that you're reading the same book, or binge the same podcasts or Spotify lists!

Do you have any passion projects on the go outside of work?

I'm a big believer in finding joy outside of the mundane. A person may have a boring 9 - 5 job, but it's telling when someone fulfills their passions outside of that. Life means something more to them. It could be woodworking, painting, passion for cooking, running, hiking, working at a soup kitchen, whatever lights up their soul. It's not only important for someone to fulfill their passions and activities that give them joy but it also encourages a healthy partnership. A partnership, where both partners have identities outside of their relationship adds layers to the relationship and makes it exciting.

It's your last night on earth, what's for dinner?

If your a die-hard foodie, this question is a must-ask. It will give you insight into their eating habits, food aversions, dislikes, or whether you'll have to rethink your meat-lovers takeout game. You'll also discover if they enjoy cooking or would rather ditch cooking altogether and order a pizza.

What's your biggest goal in life?

Goals are important. They signify drive, ambition, and they're a dreamer at heart. This will likely bring into conversation their values and what they hope their future will look like. Do they want to ditch domestic family life and live off the grid in a yurt? Do they want to climb the corporate ladder and work in a different country? Do they want to have 10 kids and live on a farm? It's a small taste of what a future could look like if you make it past the first date.

What's one thing in your life that has helped shape who you are today?

This may be a loaded question but it's a valid question. Overcoming adversity in their life no matter how big or small, taking the lesson from that experience, and putting it into practice shows integrity and grit. Life is hard and having a partner who can get in the trenches with you is essential in a partner you're going to do life with.

Want to know how to have the best first date experience ever?

  • Choose to see the date as an opportunity to meet a new friend

  • Know what you bring to the table

  • Be clear with what you're looking for in a partner

  • Don't be afraid to be open and vulnerable

  • Show up, be present, and be engaged in the experience

  • Don't try to be someone else... be unapologetically and authentically, you

Remember, you're not for everyone - that's why we must go through the process intentionally, to find a person that whole-heartedly sticks.

Hope this helps you in your dating adventures my friends. xo

Want to fall in love with yourself first?


190 views0 comments

Recent Posts

See All



bottom of page