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18 First Date Questions From The Experts

After dedicating your time searching and fielding through profiles, you finally had an online witty conversation with a possible-match and you’re ready to take your could-be relationship offline. It’s true that first dates can be one of the most nerve-wracking, anxiety-producing situations in our society. Sometimes they lead to burning love sometimes they go down in flames.

Even so, there’s nothing quite like the anticipation for the initial meet-and-greet. And while you shouldn’t prescribe too many expectations before happy hour, a bit of prep work is recommended. As dating experts agree, having a slew of good first date questions can be an easy way to maintain your banter and continue a conversation. While, sure, you know the ole’ trusty basics, what about the captivating and interesting queries that really get to the heart of your date? The key to having a positive experience is relaxed conversation, and that can be helped along with some well-chosen first-date questions.

Here, we take a look at the best first date questions you should definitely test out the next time you’re eyeing love across the table:

1. Who are the most important people in your life?
Pay attention to how your date answers this first date question. How come? More likely than not, they’ll have an instant reaction like, ‘my parents’ or ‘my college roommate’ or ‘my kids.’ In addition to understanding the other person better, this question allows you to assess his or her ability to form close relationships.

2. What makes you laugh?
In virtually every study of ‘what singles want in a partner,’ a good sense of humor ranks high. No matter the season of life they’re in, single men and women want a partner who can bring levity and lightness to the relationship. Discovering the kinds of things that make your partner laugh will tell you about his/her personality and outlook on life.

3. Where is ‘home’?
Everyone can rattle off where they currently live and where they’ve traveled before now, but the definition of ‘home’ can widely differ from where they currently pay rent. Is ‘home’ where he/she was raised? Where family lives? Where certain adventures were had? This first date question allows you to get to where their heart is tied to.

4. Do you read reviews, or just go with your gut?
Seems like a strange one, but this helps you understand differences and similarities in a simple query. Some people can’t go to the movies without reading multiple reviews first. Others can buy a brand-new vehicle without doing an iota of research. Find out which camp your date belongs in—and then you can admit if you read restaurant reviews before making date reservations.

5. Do you have a dream you’re pursuing?
At any stage of life, dreams should be nurtured, cultivated, and acted on. Hopefully, you have dreams for your future, whether they involve career achievement, world travel, volunteerism or artistic expression. You want to know if the other person’s dreams mesh with your own. Listen closely to discern if your dreams are compatible and complementary.

6. What do your Saturdays usually look like?
How discretionary time is used says a lot about a person. If she works on her ‘day off,’ she might be highly career-oriented…or maybe a workaholic. If he spends the day coaching a kids’ soccer team, it’s a good bet he loves sports, enjoys kids and wants to help others excel. If he watches TV and plays video games all day, you may have a couch potato on your hands. This question is a must, considering not all of your time spent together in a long-term relationship can be candlelit and wine-filled.

7. Where did you grow up, and what was your family like?
Eminent psychologist Karl Menninger said one of the most reliable gauges of a person’s emotional health as an adult was a stable, satisfying childhood. This doesn’t mean — of course — that you should automatically avoid someone who had a difficult upbringing. But you do want the assurance that the individual has insight into his or her family background and has sought to address lingering wounds and unhealthy patterns.

8. What’s your big passion?
This question gets to the core of a person’s being. If the individual responds with “I dunno,” that might be a red flag that he or she isn’t passionate about anything. But you’re likely to get valuable insight from the person who answers —from traveling and their children to rock climbing or their church — that give you insight into their value system. Follow up with questions about why the person become so passionate about this particular endeavor or emphasis.

9. What’s the most interesting job you’ve ever had?
No matter where they are in the career ladder, chances are your date will have at least one unusual or intriguing job to tell you about. Which will give you a chance to share about your own most fascinating work experience. Though lighthearted, this first date question gives your could-be partner the opportunity to exercise their storytelling abilities.

10. Do you have a special place you like to visit regularly?
We’ve all got our go-to spots that keep luring us back, whether they are funky coffee shops, scenic hiking trails, or relaxing weekend getaway locales. Your date may have a local park he/she frequents or a European city that’s been a regular destination. Learning where your partner likes to go will provide insight into the person’s tastes and temperament.

11. What’s your signature drink?
After the introduction and awkward hug, this opening question should follow. Though it might not lead to a long conversation, it does help you understand their personality. Does she always order the same drink? Is he addicted to fair trade coffee? Does the bartender know to bring a gin and tonic to the table before you order? Break the ice by talking about beverages.

12. What’s the best meal you’ve ever had?
Instead of asking the predictable ‘What’s your favorite kind of food?’ first date question, ask something more specific that will likely get an entertaining story about food and travel, rather than a one-word answer.

13. In which television show’s world would you most want to live?
Pop culture can both bond and divide us. Keep it light and fun and ask about the fictional world your date would most want to explore. Wouldn’t “Cheers” be a great place for a first date?

14. What’s on your bucket list?
This question offers plenty of freedom for him or her to share their dreams and interests with you. His or her list could include travel plans, career goals, personal milestones, or adrenaline-junkie adventures. Or he or she could just be psyching herself up to finally try escargot.

15. What toppings are needed to create the perfect burger?
Assuming your date’s not a vegetarian, get the conversation going with a pretty innocent—but telling—question. You’ll discover how particular your date is about his food, how adventurous his or her palate is, and if you share a love (or hatred) of mustard.

16. What’s the most embarrassing concert you’ve ever attended?
It’s easy to brag when you’re around someone new, who doesn’t know you quite yet. Turn the tables and choose to share guilty pleasures instead. Tell on yourself. Some very respectable folks have been to Barry Manilow — and/or Yo Gabba Gabba
— concerts.

17. What’s your most valuable possession?
This first date question top break the ice will help you to discover your date’s priorities, passions and pursuits. Maybe it’s a photograph. Maybe it’s a classic car. Maybe it’s a tiny trinket that represents a cherished person or memory. Putting your date on the spot might make the first answer an awkward one; let him/her amend the answer as the night goes on.

18. Who’s the most fascinating person you know?
Get to know the people in your date’s life by asking about the most fascinating one. What qualities make a person so interesting? How does your date interact with the person? Hearing your date brag about someone else might reveal more about him/her than a series of direct personal questions would.

19. What’s the hardest thing you’ve ever done? The scariest?
Instead of prying into past heartaches and failures, give him or her an opportunity to share struggles any way he/she so chooses. What obstacles does he/she define as the ‘hardest’? How did they overcome or survive the struggle? Even if the answer is a fun one, try to appreciate how strength was shown in weakness.

Now that you’re armed with some great first date questions, let’s review a few general guidelines for dating discourse:

Listen as much or more than you talk
Some people consider themselves skilled communicators because they can talk endlessly. But the ability to speak is only one part of the equation—and not the most important part. The best communication occurs with an even and equal exchange between two people. Think of conversation as a tennis match in which the players lob the ball back and forth. Each person gets a turn—and no one hogs the ball.

Peel the onion, don’t stab it with a paring knife
Getting to know someone new is like peeling an onion one thin layer at the time. It’s a slow and safe process. But some people, over-eager to get into deep and meaningful conversation, go too far too fast. They ask personal or sensitive questions that put the other person on the defensive. Should the relationship evolve, there will be plenty of time to get into weighty topics. For now, take it easy.

Don’t dump
If feeling inhibited is a problem for some people, others go to the opposite extreme: they use a date as an opportunity to purge and vent. When a person reveals too much too soon, it can give a false sense of intimacy. In reality, premature or exaggerated revelations are due more to boundary issues, unresolved pain, or self-centeredness than true intimacy.

Now that you’ve got questions for your first date, try setting one up on eHarmony.

Try: What is Love? or Love at First Sight