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20 first date questions that'll show if you're a good match

Start with a few funny icebreakers, then go all in with these deep (and very important) Qs.

Deep, meaningful conversations are the gateway to intimacy in relationships. While, yes, all good things take time, there are some key questions to ask on a first date to lead you in the right direction (if you're seeking something serious, that is).

Generally speaking, first dates are either the start of something new and exciting — or a start to a quick end. By asking the right questions, you'll get a sense of where this relationship is headed, all while keeping a steady flow of conversation.

Of course, navigating the modern dating realm can feel like entering a galaxy far, far away, which is why we've tapped two love and relationship experts for guidance. Below, Rachel Hoffman, chief clinical officer at Real, and James Preece, an international dating coach, weigh in on which questions you should ask your date — and why.

It's your call how many questions you want to ask and how you choose to word them. And really, if the chemistry is there, you may find that these questions may naturally come up in conversation.

Now, take a look at these expert-approved questions to head into your first date with confidence. Good luck!

1. What's your family like?

Asking about your date's family, friends and community is a great way in. "Learning about someone’s relationships can be really helpful in understanding someone’s mezzo system, meaning their connections to the small groups around them," Hoffman told TODAY.

2. How long have you two been friends?  

A follow-up to the first question can be about the people your date mentioned. “If they bring up specific names of important humans in their life, I would ask more about those specific individuals," Hoffman said. "Learning who the person you are on a date with wants to spend their time with is valuable information."

3. Are you still close with college friends?

Asking about the state of their friendships can determine how they value friendship, according to Hoffman. At its core, a romantic relationship is a deep friendship, so this is important to know before you go any further.

4. What are the top three items on your bucket list?

Preece suggests asking this question to get personal without getting too personal. Who knows, you may find that you have the same items on your list. Talk about kismet!

5. What do you do for fun? 

Of course, there is more to a person than their day job. Asking about someone’s hobbies and personal interests can tell you more about what they're really like. Perhaps, it'll even inspire your next date.

6. If you had to donate money to a charity, which charity and why? 

Find out if they volunteer or donate regularly, or have a cause that's close to their heart. “Maybe they will tell you a personal anecdote that will explain this in more detail," Preece said.

7. What did you do this past weekend?

If you’re seeking a soft opener, simply asking about their past weekend or week can give you a little insight into their day-to-day life.

8. Would you rather win $1 million for surviving being dropped in the desert or swimming with sharks?

Preece recommends "Would You Rather?" questions. Not only are they a way to keep your date on their toes, but they'll often lead to unconventional conversations about, say, swimming with sharks.

9. How do you de-stress after a tough day? 

This low-lift question is a great way to get things flowing. “Sometimes starting with these questions is a bit easier and can lead you naturally into the questions about family and friends," Hoffman said. "If they mention specific hobbies and interests you can follow up with the question, 'Were you with anyone?'" From there, you can dig deeper into their friendships, relationships with family, their career and other important topics.

10. If they made a film of your life, who would play you? 

Why not bring up your celebrity doppelgänger on a first date? Preece says you can tell a lot about a person based on the celebrity they name. Do they pick a well-known actor or someone under the radar? Their answer will reveal how they see themselves.

11. What is your love language?

It's better to get this question out of the way now. Hoffman says that knowing their love language — words of affirmation, quality time, receiving gifts, acts of service, and physical touch — will help answer bigger questions down the road.

 12. If you could choose a superpower, what would it be? 

This is where things will really heat up — kidding, kind of. Reveal your chosen superhero power of choice and see what your date picks. Just be warned: Somehow, it may lead into a fiery Marvel vs. DC Comics debate.

13. What's your guilty pleasure?

Everyone's got one, so Preece says coming clean about yours — whether it's cheesy movies, power ballads or a big ol' jar of Nutella —can help you two bond.

14. If you had to re-do one year of your life over, which one would it be and why?

A little deeper of a question, this one may be better for later on in the date if, well, sparks are flying. Their answer will provide insight into their past — the good, the bad, the questionable — which ultimately affects their future (with you).

 15. What's your hidden talent? 

Less talk, more action: Preece says this question invites some show and tell. But be prepared to show off your hidden talent after they demonstrate theirs.

16. What's the most memorable place you've visited?

This one's crucial for travel lovers. With this query, you'll learn how adventurous they are and can follow up by asking where they'd like to go next.

17. Would you tell someone if you knew their partner was cheating on them? 

Consider this to be the ultimate test. You'll learn a lot about a person by asking this question since, as Preece says, it "unwraps their moral compass."

18. How did you find the pandemic?

While you don't necessarily want to bring the mood down, the pandemic unified all of us — including you and your date. Along with making sure you're on the same page about safety measures, be sure to ask them their general feelings about the last few years. “You’ll find out if they see life in a more positive or negative way based on how they answer,” Preece said.

19. What are you most proud of? 

Everyone loves to talk about themselves — especially if it paints them in a good light. This question, in particular, opens a doorway to deeper conversations, according to Hoffman.

20. So, what are our next steps?

Maybe, just maybe, this is the most important question of all! “This is the most important question of all, but one people are most reluctant to ask," Preece said. "If you like them, then let them know and you won’t have to spend days wondering if they are interested."