10 Questions to Ask on a Date


Just getting the date is the first step. Knowing which questions to ask can lead to some very revealing answers.“Just getting the date is the first step. Knowing which questions to ask can lead to some very revealing answers.Allan Danahar/Digital Vision/Thinkstock

So you’ve convinced someone to go on a date with you — congratulations! After you’ve agonized over finding the perfect outfit, fixed your hair so you look your very best and made sure you don’t smell funny, you have high hopes that the rest of the evening will go smoothly. You arrive at the restaurant, spend a few minutes perusing the menu and — after the meal has been ordered — the real date finally begins. Now is the time to get to know the guy or girl who caught your eye. But what are you supposed to talk about?

Whether it’s your first date or your 50th, sometimes coming up with interesting topics of conversation can be a challenge. There are so many things you want to know about the person sitting across from you, but how do you pry into his or her personal life without coming across like it’s an interrogation?

Here are 10 questions sure to spark good conversation while letting you find out more about your potential love interest.


  1. What's the best part about your job?
  2. If you could listen to only five albums for the rest of your life, which ones would you choose?
  3. What one movie do you never get sick of?
  4. What is the weirdest thing about you?
  5. If you had the opportunity to spend a week anywhere in the world, where would you go?
  6. What was your favorite TV show growing up?
  7. Are you the oldest, the youngest or a middle child?
  8. If you were stranded on a deserted island, what would you do?
  9. What's the best thing you've ever eaten?
  10. Can I see you again?

10: What's the best part about your job?

If you don’t already know what your would-be partner does for a living, it’s probably one of the first things you’re interested in finding out. After all, a person’s job says a lot — is he financially stable? Is she creative or structured? Does your date even have a job? But rather than just simply asking where your companion spends the largest part of the day, why not dig a little deeper? Asking about a job’s best aspects sets a positive tone and steers the career question away from negativity and spontaneous rantings about a horrible boss.

Plus, it’s a good question to ask if they’ve already told you where they work but you can’t quite remember.

Keep it Light

Dates should be fun, and though deep confessionals can be great at strengthening the relationship later on, the first date isn’t exactly the best time to air out the skeletons in your closet. In her book, "Why He Didn’t Call You Back," best-selling author, speaker and dating coach Rachel Greenwald says, "Your first date should be more like Reader’s Digest than Encyclopedia Britannica. Keep your conversation light and interesting, and save the serious history for later" [source: Greenwald].

9: If you could listen to only five albums for the rest of your life, which ones would you choose?

A person’s taste in music reveals a lot about personality. Does your date like the twang of country, the steady rhythm of drum and bass or a jam-band bootleg? But instead of just asking what music your date enjoys, evoke decision-making skills by narrowing it down to a personal top five. Sure, you may like the latest pop diva now, but would you tire of her crooning if you had to hear her all the time?

According to a study by psychologists, your music choices reveal a lot about your personality — more so than the way you dress, your political views or even the movies you like. In fact, after listening to a compilation of songs chosen by a single person, people can make a fairly accurate assessment of major personality traits, like whether you’re an introvert or an extrovert [source: Harlow].

Plus, maybe she’ll be really into that obscure band you love that you thought nobody else had ever heard of.

8: What one movie do you never get sick of?

Some movies are just as good the 30th time as they were the first, so what flick captures your date’s attention time and time again? Asking about film faves is always a great conversation starter. And even though movie choices don’t tell you as much about someone’s personality as their music choices, everyone loves talking about their favorite flicks. If this question sparks your date’s interest, you could even take it further — what is the scariest movie you’ve ever seen? What was the funniest?

And don’t forget the biggest benefit of this line of questioning: It could lead to the suggestion of seeing a movie for your next date.

Don’t Forget to Listen

While it’s good to have a repertoire of questions and topics of conversation you can use on a date, don’t forget to listen to your date’s answers. If he tells you he’s allergic to chocolate, then you ask him if he’d like to share a hot fudge sundae, it’s immediately clear to your date that you haven’t been paying attention. Really listening to what your date is saying not only shows him you’re interested, but also helps you to find out if he’s the right guy for you.

7: What is the weirdest thing about you?

Though it’s unlikely your date will reveal his or her deepest darkest secrets too early in the relationship, this question does present an interesting challenge. Does she have a weird habit that you never would have guessed? What about a secret talent that makes him unique? This question can be exciting because it’s likely neither of you will be sure just how much to reveal. So have fun with it (without freaking your date out too much).

But remember — while this can be a fun question to make your date squirm, be prepared for the question to be thrown right back at you!

When to Change the Subject

So what if your date tells you the weirdest thing about him and it makes you question your decision to have accepted the date in the first place? Time to change the subject! The truth is, not every question is foolproof — most people have some subjects that just make them uncomfortable. If your date seems put off by your line of questioning, it might be time to change the subject to something a little more neutral — such as music or movies.

6: If you had the opportunity to spend a week anywhere in the world, where would you go?

This question is great for finding out about your date’s sense of adventure. Is her dream vacation a relaxing week on the beach in the Bahamas? Or has she always wanted to freeze her fingers off at an ice hotel in Finland? What about mountain climbing in Argentina?

Whether your date tells you she’d like to travel to the other side of the globe or that she’d jump at the chance to spend some time in her childhood home town, this question sets the conversation rolling about travels made, travels planned and travels only dreamed about. Maybe your jet-setting ambitions will coincide, but even if they don’t, it’s definitely one way to find out your date’s idea of a good time.

5: What was your favorite TV show growing up?

Who doesn’t love reminiscing about their favorite Saturday morning cartoons or guilty-pleasure sitcoms? Do you feel nostalgic whenever someone hums the theme song to an old favorite? Was there a show you never missed a single episode of? Instead of asking what modern-day TV shows your date records each week, find out what series brings back happy memories of a time when life was simpler. Chances are you’ll discover a show or two that you both used to love when you were kids. Have a few good laughs and recall the goofy characters and cheesy storylines of the popular shows of your childhood.

4: Are you the oldest, the youngest or a middle child?

Here’s one way to bring up the topic of family without sounding like you’re overly eager to become part of it. Studies show that birth order plays a role in personality development. Is he a competitive first born, an intense second born, a sympathetic third born or an emotional only child? Even though the basic characteristics can vary from person to person, and no two people are the same, finding out his role in his family can give you insight into his personality and character [source: Isaacson]. It’s also a good way to get a feel for his relationship with his family without the risk of dredging up potentially negative feelings.

3: If you were stranded on a deserted island, what would you do?

Tap into your date’s primal instincts and find out if he learned how to build a fire in Boy Scouts or if he knows how to catch a fish with his bare hands. What would he do if he found himself alone in the middle of nowhere? Would he immediately go into survival mode, building a hut for shelter and finding the nearest source of water, or would he panic?

It’s a question your date likely hasn’t thought about the answer to — and it could certainly be entertaining, especially if he or she is the type of person who wouldn’t know how to function without a cell phone and Internet access.

Should you prepare questions ahead of time?

Getting ready for a date can involve a lot of anxiety and preparation, but is it really necessary to come up with a list of questions ahead of time? For the conversationally challenged, it wouldn’t hurt to at least think of some topics of conversation before the big date, but writing them down isn’t necessary. At the very least, think of a few topics or questions to help ease any awkward silences.

2: What's the best thing you've ever eaten?

Asking your date which foods ranks at the top of the favorites list could spark an idea for your next outing.“Asking your date which foods ranks at the top of the favorites list could spark an idea for your next outing.Digital Vision/Thinkstock

Does she drool just thinking about mom’s spaghetti and meatballs, or does she prefer an elegant meal at a five-star restaurant? Food is generally a safe topic because it’s something most people enjoy. Pretty much everyone could name a favorite food or two, and it’s a fun way to gauge how adventurous of an eater your date is. From there you can even ask if he likes to cook or what his favorite meal to make is. Is he a culinary genius or a macaroni and cheese kind of guy? Does she like to have big family meals, or does she prefer to order a pizza?

And don’t forget your companion’s answer to this question — it could be instrumental in deciding where to go on your next date!

1: Can I see you again?

Don’t forget to end a great date by making plans for another one! Whether you call her up a few days later, send an e-mail when you get home or ask her on the spot, don’t forget to make it known that you’d love for there to be a future meeting. Be sure your date knows you’ve enjoyed her company and she’ll leave feeling good about it. Life’s too short for games, so if you had fun and would like to do it again some time, just ask!

But what if it doesn’t work out? Luckily there are plenty of ways to meet people, and there’s lots more information on the next page.

Lots More Information

Related Articles

  • 10 Dating Faux Pas
  • 5 First Date Ideas
  • 5 Tips for Talking With a Girl on the Phone
  • 10 Steps to a More Intimate Relationship


  • Greenwald, Rachel. "Why He Didn’t Call You Back: 1,000 Guys Reveal What They Really Thought About You After Your Date." Random House, 2009.
  • Harlow, John, and Laura St Quinton. "Focus: What your taste in music says about you." The Sunday Times. Jan. 15, 2006. (Oct. 1, 2010)http://www.timesonline.co.uk/tol/news/uk/article788601.ece
  • Isaacson, Clifford E. and Kris Radish. "The Birth Order Effect: How to Better Understand Yourself and Others." Adams Media, 2002.
  • Rogers, Victorya Michaels. "The Automatic 2nd Date: Everything to Say and Do on the First Date to Guarantee…" Simon and Schuster, 2007.


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