11 Good First Date Questions

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First dates can be a little nerve-wracking, especially when awkward silences set in. The next time you face a dreaded lull in first date conversation, try one of these great first date questions:

1. How was your day?

It’s a simple question, and one that’s too easily forgotten. Ask your date about his/her day, inquiring about the highs and lows in the hours prior to your meeting. The answer might reveal plenty about how the individual deals with stress, what little joys he/she cherishes, and why he/she looks a little preoccupied.

2. What’s your signature drink?

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 — then buy her one.

3. What’s the best meal you’ve ever had?

Instead of asking the predictable “What’s your favorite kind of food?” question, ask something more specific: What was your date’s best meal thus far? You’ll likely get an entertaining story about food rather than a one-word answer.

Related: What’s your go-to dish to bring to a potluck? Do you make it from scratch, or do you bring something store bought?

4. 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?

5. How do you define success?

After you’ve talked about careers, hobbies and free time, ask about success. What does it look like? Maybe your date has a career benchmark he’s hoping to reach before he turns 40. Maybe she wants a family and a summer home. Maybe he just wants to look back at his life with no regrets. As this question can be personal, be prepared with your own answer when you ask this.

6. 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?

7. Who do you go to when you need advice?

Inquire about the person your date trusts most and you’ll learn plenty about his/her value system and the sorts of people who are important in his/her life.

8. When you were a kid, what did you want to be when you grew up?

Get to know your date’s younger self by asking about old dreams. When did the childhood dream change? Did it? What would his/her younger self think about the present day version?

9. What’s your most valuable possession?

Asking about the tangible things your date values will help you 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.

10. 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.

11. What’s the hardest thing you’ve ever done? The scariest?

Instead of prying into past heartaches and failures, give your date 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.


More dating advice:Pickup Lines for just about any place, Biggest signs he is in love with you

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