Imagine you’re on a date and you sit down in the nice restaurant. You order wine and check out your companion. She’s really cute and has a nice smile. After a few moments, the smiling turns a tiny bit awkward and since you don’t know what else to ask, you blurt out “So…. Tell me about yourself.”

No. No. No. This is waaay too much of a broad question. She will feel on-the-spot and will probably mumble something along the lines of “I like reading” – an equally boring answer that tells you NOTHING whatsoever about her.

So how the hell do you assess compatibility, find out her interests, passions, aspirations and personality traits? Through kickass first date conversation starters that are really fucking engaging. Here’s 30 to get the ball rolling:

Who is your favourite Disney villain?

• More exciting than asking who her favorite Princess is. Does she sympathize with people portrayed as villains and see that good and evil are not simply categorized?

Who are three of the most important people in your life?

Learn why she values people.

What are you watching on Netflix right now?

• Find out whether she likes Netflix and what kind of things she likes watching.

What is the worst thing someone could do on a date with you?

• Find out what she hates on dates – so you don’t do the same.

What is your biggest fear?

• Find out what makes her feel afraid and be prepared to see a more vulnerable side to her.

How do you like to spend your day?

• Find out what she prioritizes and what daily things make her feel happy.

Do you work best in the morning or the evening?

• Find out about her routine and body clock.

Do you keep in touch with people you no longer see regularly?

• Learn how much she values relationships and loyalty.

What did you want to be when you were a child?

• This will make her think deeply about their life and remember good times, hopes and dreams etc. You can also learn about her childhood.

What is a skill you wish you had?

• See what skills she already has and what she think would be important.

What is your family like?

• It’s important to see how functional/dysfunctional her family is and what the dynamics are.

What has been the best part of this year?

• Make her reflect and think positively. Find out what she thinks makes a period of time good.

If you were given a lump sum of money to start a business, what kind of business would you start?

• Learn how creative, intelligent and ambitious she is and possibly what kind of a leader she’d be.

What does your dream home look like?

• See what kind of an environment she’d like to live in.

If you could pursue any career, what would you choose to do?

• Find out about her talents and ambitions.

What is your Myers Briggs type?

• See how compatible she is to you and how she solves problems.

Are you an introvert or an extrovert?

• Find out about how she deals with events and communicates.

Do you think that money makes the world go round?

• Find out what value they place on money and what they think of the wider world.

If you’re in a team-working task, what role do you take on?

• Finding out how she works in a team will allow you to get an idea of your compatibility.

What is your favorite drink?

• Find out about her taste with this easy first date conversation starter and possibly order that drink to set a positive tone to the date.

Do you like tattoos?

• See if she’s artistic, a bit badass or has different views on tattoos.

Have you ever read a book that changed the way you thought?

• Find out if she enjoys reading and how she analyses things she reads.

What is a saying that you try to live by in life?

• Find out what motivates her and her morality.

If you had three wishes in life, what would they be?

• Find out dreams and priorities and pretend to be a genie.

If you won the lottery, what would you do with the money?

• Again, dreams, priorities and ambitions. See if she’s a giver as well.

If you really like something on the menu, do you always order the same thing?

• See how much she values ingrained habits.

What is the best thing about your personality?

• Give her a chance to brag and tell you why she’s great. It will make her happy and you can see what she values in herself.

Do you find it easier to gain knowledge through books or hands-on experience?

• Find out how she learns new information best.

If you could invite anyone in the world to a dinner party, who would you invite?

• See what kind of people she respects and what qualities she admires.

What is your favorite way to stay healthy?

• A more subtle and positive way of learning about her health and fitness than “Do you workout?”

You’re welcome 😉. Some key points to remember:

  • Listen and try and turn these questions into conversations; don’t just fire them at her non-stop like an over-zealous interviewer. Good conversation releases oxytocin in the brain and makes everyone happy and more likely to empathize. Bad conversation, well, doesn’t. Build a flow.

  • Some of them, e.g. the ‘biggest fear’ one require for the date to warm up a little, so while it’s a conversation starter, it’s NOT the first question you ask on the date.

  • These questions aren’t all about you passing some sort of ‘test' to not look awkward. It’s also about assessing how compatible your date is with you. The power lies in your hands.

If you found these helpful, I actually compiled a list of 101 first date conversation starters, with more like these, plus deeper questions to ask as the date progresses. There’s more tips and the questions are colour-coded in this link 😊. Let's make the world a better place for first dates.