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30 First Date Conversation Starters That will Guarantee A Good Time

Crappy conversations are the number one thing that can ruin a first date and give a woman a negative first impression of you. You’ll need icebreakers, lighthearted queries, and questions that spark banter, humour, and thought, as well as questions that go a dig a bit deeper and go beyond the surface.
To save you from endless awkward silences, CherryDTV have compiled some first date conversation starters.

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1. If you could get on a plane right now, where would you go?

Who doesn’t love to travel? Hermits, that’s who. If she hates planes, road trips, or has no desire to leave her hometown ever, that’s a good indicator of her ambitions and desires (or lackthereof). Otherwise, this question will excite her and you’ll learn what’s most appealing to her.

2. What are you most passionate about?

This question allows you to get a feeling of what she cares about and whether she’s vivacious and authentic. It’s also an excellent way to see if her degree of enthusiasm matches yours.

3. What’s your dream job?

This is an excellent question because a dream job combines meaning, passion, and a way of life. Her explanation will be quite telling. Is it for the money, the impact, or the pleasure? Each of these explanations reveals something unique about her personality.

4. If work was no longer an option and you had plenty of money, what would you do all day?

This conversation starter can give your mix of questions a light, playful, unrestrained atmosphere. It’s also fascinating to hear other people’s responses. If she’d watch every television show ever made and you’re an active person who can’t tolerate being inside, you’re probably not going to be super compatible.

5. What’s been the most significant or best year of your life so far?

If you want the conversation to become a bit reflective, thoughtful, and meaningful, this is a great fall-back. Not only do you get to hear about her life story, but the snippet that’s most meaningful and important to her.

6. What’s one thing you did as a kid that you miss most today?

She’ll get a little reminiscent with this conversation starter. It’s playful. And who knows, maybe you went to the same camp or holiday spot each summer. It’s fun to see what you might have had in common as kids.

7. Who do you talk to the most?

You’ll learn about the people closest to her in life. You can see if she has a tight bond with her parents or siblings. Or you might even find out if she’s still hung up on an ex. The five people we’re around the most, shape us the most and her relationship to any one of her closest friends and family members tell you a lot about her.

8. What are 5 things you want to accomplish before you die?

You’ll get major insight on her goals and priorities in life. You can gauge whether she’s philanthropic, an outdoor buff with a killer bucket list, and everything in between.

9. What is your favourite dish to cook?

You’ll learn about her culinary skills, what food she likes, if she’s into healthy cooking, and has any favourite restaurants, Food is always a safe topic of conversation and an endless one, too.

10. What are your favourite sports?

If sports are big in your life, this will take you into a ton of subtopics. Ask what sports she’s interested in, what teams she roots for, and if she’s ever played sports. Depending on her answer, you can see whether you’re up for some healthy competition or standing behind the same teams. And if she doesn’t care, then you can decide whether it’s a slight turn off or a deal breaker.

11. Who has been the most influential person in your life?

Instead of asking “Who is the most influential person in your life?” instead of “How close are you to your family?” This will reveal more about her family dynamics as well as her close friendships.

12. If you were stranded on an island and could take three things with you, what would they be?

Catching her off guard is a good thing so long as your intentions are innocent and playful. Despite the quirkiness of this question, you’ll find out what’s most valuable to her and the significance of those items.

13. What’s the most spontaneous thing you’ve ever done?

Is she a thrill-seeker or a free spirit? You’ll find out if she’s been running with bulls or scaled a mountain. This is a great question to see how flexible she is. You can see if your personalities and interests align, too.

14. What is your biggest pet peeve?

Ask about the little things that drive her nuts. Obviously you’ll get an insight on her temperament. But you’ll also be able to reign in any bad habits that might prevent you from having a second date.

15. How do you like to spend your mornings?

It might seem super particular, but her morning routine is hugely revealing. Does she wake up, get ready, and rush to work with minutes to spare? Does she wake up, lounge around, read a newspaper, then get ready for work? Or does she meditate, go for a six-mile run, shower, and make a gourmet breakfast before heading out the door? These scenarios are snapshots of three incredibly different people and personality types.

16. How do you like to spend your nights?

Like the previous question, this one clues you in on how she spends most of her time and whether you’ll enjoy the same activities. You may love going out to bars and clubs for karaoke on a Saturday night while she’d rather binge-watch the latest Netflix series. You’ll see early on whether you’ll clash.

17. What are you most afraid of?

This question can go the trivial or serious route. Try both. See what childhood fear she still has: Maybe she’s terrified of spiders, darkness, and basements. And ask what she’s most afraid of in life: Is she afraid of failing in her job, never getting the opportunity to travel, mending a particular relationship? You’ll see a vulnerable side of her without being too forward.

18. Are there misconceptions about yourself you wish people wouldn’t make?

This is a ballsy question, so use your discretion. In the right context, though, it can let her clear the air or dispel any frustrating assumptions people make about her. Let her take this question where she wants, and don’t be too pushy.

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19. What do you wish you were better at?

Ask her what skills she wants to acquire or hone in her career and life in general. If she’s ambitious, that can be a major turn on. It’ll also show you she’s humble and doesn’t hold herself too high if she points out some areas she wants to improve.

20. What did you want to be growing up?

Both of you get the floor to speak about your childhood. You’ll have endless stories… chock-full of embarrassing confessions and lofty dreams.

21. What’s your favorite childhood memory?

You want positive vibes only on a date. By posing this question, you get her thinking about some of the best times in her life. You’ll also get a peek into family traditions and dynamics.

22. What’s the most embarrassing thing that’s ever happened to you?

Share a funny story at your own expense first. It’ll show her you have a sense of humor and can laugh at yourself. Then, she’ll be more inclined to do the same.

23. Where can you see yourself living?

This question is more revealing than you’d think. If she has plans to move to Germany next year, she might not be in a place in her life where a long-term relationship is feasible. Likewise, if you’re deadset on living in a city, whereas she’s dying to live on a farm, there are going to be conflicting desires that can spell disaster for a relationship.

24. What’s your favorite way to get active?

If you’re on this website, fitness and health are obviosuly important to you. Instead of asking her if she works out, see what her favorite physical activities are instead.

25. What talent do you wish you had?

See what talents she admires. If she’s always yearning to learn something new, it shows she’s inquisitive. It can also open the idea of trying something new together—like cooking—on a second date.

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26. What’s been your biggest regret in life?

Like some of the other questions on this list, feel out the conversation and only ask this one if the moment feels right as it could make her feel uncomfortable. Try to slip it in to conversation if she mentions a career path she could have gone down or a trip of a lifetime she never took. Just tread lightly.

27. What would you be doing if you weren’t in your current job?

This is a twist on the “dream career” question, but will result in an answer like “lawyer” rather than “movie star.” What she went to school for may not be the field she’s in now. Likewise, what she studied in school may not be her dream career anymore. This is a fun way to pick her brain and get her talking about what her interests and passions are.

30. What are you kind of obsessed with these days?

With this question you’ll find out her interests, what motivates her and what keeps her attention!

Have fun getting to know each other!

Use these conversation starters to dig deeper and keep your date enthusiastically attentive towards you. Asking these questions with genuine curiosity will allow for a stronger connection between you and your date and will have her feeling like you actually want to know her, you’ll make her feel good and you might even learn someone thing new about yourself along the way! Happy dating!

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