in: Featured, People, Relationships

• Last updated: May 29, 2021

How to Ask Better Questions on a First Date

Man and lady on a first date having tea.

Engaging in small talk with anyone can be a little nerve-racking — you’re on an improv stage for two, and have to think of things to say on the fly, avoid awkward silences, and come off as at least moderately charming to boot.

Engaging in small talk on a first date can be especially anxiety-ridden. While unspoken, you’re being actively evaluated on your attractiveness (both in personality and looks). It’s like a “job” interview for the position of potential significant other. Ace it, and it could be the start of a lifelong love affair. Blow it, and you might never see that someone special again.

No pressure, right?

As an aid in being successful at this kind of high-stakes small talk, you can find plenty of lists out there which suggest good questions to ask someone on a first date.

These lists tend to fall into two categories: basic, stock questions (“Where are you from?” “What do you do for fun?”), and more unique, out-there questions (“If you could only bring 3 things with you on a desert island, what would they be?”).

The problem with the first set of questions is that they’re boring; if someone is dating a lot, they get tired of being asked if they like their job and how many siblings they have. The problem with the second set, is that they can seem pretty random — and overly scripted — if you just drop them into conversation.

Fortunately, it doesn’t have to be an either-or equation. There’s a better way to ask first date questions that incorporates both types of them.

You do use the basic, stock questions — common though they are, they form a comforting ritual that puts people at ease. But, you use them as jumping off points, which allow you to segue into more interesting questions.

This approach strikes a nice balance between seeming like you’re trying too little, and coming off like you’re trying too hard.

You ask a standard stock question, and then act like your date’s response to that question just naturally made you think of another semi-related, more unique one. Of course, you had the question in mind already, and that’s okay. The paradox of being charming is that in order to act natural, you actually have to be well-prepared; it’s not that people don’t know on some level that your repertoire is somewhat “scripted,” it’s just that if you execute it smoothly and engagingly enough, they don’t care, and enjoy coming along for the ride.

How to Ask Better First Date Questions With the Standard-Question → Interesting-Follow-Up Method 

The beauty of the standard-question → interesting-follow-up approach is that it will take your first date conversations to places where you’ll indirectly get to know a whole lot about the other person, without directly — and awkwardly — having to ask them, “What is your deepest fear?” or “Where do you see yourself in five years?”

While your questions should be thought-provoking, your partner should be able to answer them without missing too much of a beat; people feel dumb when they have to do the “Hmmm, boy, well, oooh, that’s a tough one” thing, and struggle to come up with a response. A good gauge of whether a question hits the sweet spot is simply to ask yourself the question, and see if you both enjoy thinking about it and can pretty readily imagine how you’d respond.

Also, remember that a conversation isn’t an interrogation — you don’t want to ask question after question without sharing anything about yourself. Your date will hopefully turn these questions back on you, and come up with ones of their own. If they don’t, though, pepper in some commentary about your own life; research has shown that people who reveal more about themselves (while making such disclosures within appropriate guidelines) are liked more than those who are more guarded. Of course, if your date is a conversational narcissist, it’s likely an ill omen of things to come.

Finally, while the follow-up question doesn’t have to exactly relate to the standard question you first forward, obviously the more closely it does relate, the more natural the segue will be. So choose a follow-up in the moment, based on what your date has said, and connect it to something she offered in her response.

Standard Question: Where are you from originally?

Interesting Follow-Ups:

  • Was it a fun place for a kid to grow up? As a child did you wish you lived somewhere else?
  • Other than that town/city, is there another place that feels like “home” to you?
  • If I was visiting your hometown, what’s the top thing you’d recommend seeing or doing?

Standard Question: How many siblings do you have? 

Interesting Follow-Ups:

  • What was your “identity” in the family? You know, some kids are the overachiever, or the goody-two-shoes, or the wild one, or the peacemaker. What was your M.O.?
  • Are/were you closer to one sibling in particular?
  • In what ways are you different from your siblings?

Standard Question: What brought you to this city?

Interesting Follow-Ups: 

  • What’s turned out to be the most different from the conceptions/expectations you had about this place before you moved here — what you imagined it would be like before you came?
  • What’s your favorite thing about living here?
  • What’s one thing about this city you weren’t sure about at first, but have grown to appreciate?
  • What’s one downside of living here that you don’t think you’ll ever get used to?

Standard Question: Where did you go to school?

Interesting Follow-Ups: 

  • Did college meet the expectations you had of what college would be like growing up?
  • What’s one thing you wished you had known going into college? Do you have any regrets about how you did college?
  • What do you miss most about your college days?
  • When did you know what you wanted to major in?
  • Is your work now related to your major?
  • Have you stayed in touch with your high school/college friends?
  • How did you meet your best friend?
  • What would most surprise your high school/college friends about how you’ve changed since then?
  • What do you think’s been the hardest part of becoming an adult?

Standard Question: What do you do for work? Do you like it?

Interesting Follow-Ups:

  • What’s lacking about your job that keeps it from being a dream job?
  • What are your hours/schedule like? Do you like that schedule or are you more of a morning person/night owl by nature?
  • What’s a part of your morning routine that helps you have a good day?
  • How do you like to unwind when you get home? 

Standard Question: Do you have any favorite television shows?

 Interesting Follow-Ups: 

  • What’s a television show you think got canceled too early?
  • What’s a show you watch when you can’t figure out what to watch?
  • Is there anything you could re-watch over and over again?

Standard Question: What kind of music do you like?

Interesting Follow-Ups:

  • What’s the best concert you ever attended? Worst?
  • What’s the most embarrassing concert you’ve ever attended (e.g., One Direction, 10th grade)?
  • What’s an album you never get tired of?
  • Is there a genre of music you loved in high school, that you now can’t stand?
  • What’s on your workout playlist?

Standard Question: Read any good books lately?

Interesting Follow-Ups:

  • What was your favorite book you had to read in high school?
  • Are there any books you love so much you’ve read them twice (or more)?
  • Is there a book, that’s not necessarily your favorite, but that you find popping into your head the most often?

Standard Question: Do you have any hobbies? What do you like to do on the weekend?

Interesting Follow-Ups:

  • What’s a hobby you’d really like to get into if money/time wasn’t an issue?
  • What hobby did you pick up and drop the quickest?

Standard Question: Do you like to travel? Have you taken any trips recently? 

Interesting Follow-Ups:

  • Is there a special place/destination you like to visit regularly/return to again and again?
  • Is there some place you visited that really disappointed your expectations?
  • Is there a place you visited that exceeded your expectations?
  • When you’re visiting a new city, what attraction do you have to visit first?
  • If you had to live full-time in an RV or on a sailboat, which would you choose?
  • Would you prefer to take a vacation to the mountains or the ocean? Did you know that research says people who prefer the mountains are more introverted and people who prefer the beach are more extroverted? Do you consider yourself more introverted or extroverted?

Just a generally good question to ask: What’s something you’re looking forward to in the near future?

Follow the standard-question → interesting-follow-up structure laid out above, and your conversations will flow smoothly, you’ll cover a lot of ground, and you’ll never run out of things to talk about on a first date!

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