The Best Date of Your Life: Our Ultimate Guide to First Date Conversations

On that glorious, nerve-wracking, thrilling first date, questions can flow thick and fast. When the romance is hot and the chemistry electric, you’re dying to find out everything you can about one another. It’s seriously exciting.

All that being said, there are still a few pointers to be aware of when asking (and even answering) questions on your date to ensure things go swimmingly. After all, in the excitement it’s easy to get carried away and accidentally ask something a little too probing or personal. Make no mistake: if you start dating this person properly, eventually you do need to delve into the deeper stuff. That’s how you form the foundation of a solid relationship. But when you’ve just begun seeing each other—when you’re still floating in the transcendent haze of those dreamy first dates—it’s generally best to keep things casual. These times are all about getting comfortable with each other, assessing the compatibility of your personalities. If all that goes well, you’ve plenty of time to sit down for the more profound questions.

Getting in the zone

It’s simple, right? You’ve been asking questions all your life. You ask them every day without even thinking about it. In fact, you’re something of a pro.

…Except it’s a very different story when you’re on a date. You’re excited but jittery; you’re effervescing at the idea of spending quality time with this hot new romantic interest, but you’re eager to come across as your best self, too. Nerves are normal. So if you prepare yourself in advance—not only with some great questions, but also just by thinking about how you actually ask them—you’ll be on to a winner.

Keep things light and open

First, think about things you could ask your date—ahead of time. These can be your go-to questions if the wine temporarily numbs your lips and your mind—or when you’re stunned into silence by how damn sexy they look in the dim light of the bar. Keep them basic—otherwise you’ll struggle to remember them!

  • “How was your day?”
  • “So what brought you to the city originally?”
  • “Where did you grow up?”

You can also try out some fun hypothetical questions:

  • “You can only take three possessions to a desert island. What makes the cut?”
  • “Which three people are you inviting to your ultimate dinner party (dead or alive)?” (You’ll have noticed a pattern here: three is indeed the magic number. Big enough to generate some thought—small enough that the effort doesn’t become laborious.)
  • “What would be your perfect Sunday?” (Hey, clichés are clichés for a reason—they work!)

Hypothetical questions let the conversation go off on some hilarious tangents—and sometimes they can become surprisingly fascinating. They actually provide a valuable window into how your date’s mind works, and their answers often represent more deeply what they value—who they are.

Perhaps the best type of questions revolve around hobbies and interests. These generally elicit non-political answers (more on why that’s important later), and allow your date to come into their own as they expound on their passions and what drives them in life. People so often have the most unexpected pastimes, and you may see a whole new side to this new romantic interest of yours. Remember, hobbies are not a trivial matter: they are, in a sense, what we’d like to do all the time if time and money were no object. Discussing your interest can also serve to reveal deeper connections between the two of you, and galvanise secret fleeting fantasies of taking up some of these pastimes together, as a team—as a couple.

And one more key point to remember when you’re nervously pacing outside the bar awaiting their arrival: the two of you are on this date because you like the look of one another. Conversation will flow, if for no other reason than the fact that you’re attracted to and interested in each other. These questions we’re exploring today aren’t Q&A-style, over in a sentence or two—they’re portals to entire conversations, in which you both become totally absorbed in the other, in which time stands still—but also jumps ahead by half an hour without you realising it. So in those heady moments between them appearing down the road and reaching you, your mind may go blank. You may gaze in wonder at how mighty fine they’re looking tonight. Words may escape you. That’s fine. That’s normal. That’s what it’s all about. With your go-to questions to hand, you’re all set. You’ve got this.

Remember these 2 vital nonverbal skills

1. Active listening

To the uninformed, listening might seem the easiest thing in the world. You keep quiet, you maintain eye contact, and you don’t interrupt. Right?

Well… kind of. But they’re the basics. Active listening is a skill unto itself. And as you hone it, you’ll become a far more compelling communicator—without saying a word.

Active listening is all about being present. Your date’s words aren’t going in one ear and out the other—you’re genuinely taking them in and visualising the conversation before your eyes. If they’re rambling, you know what? It doesn’t matter—stick with it. Unless they’re talking at inordinate length because they’re arrogant, chances are they’re simply nervous and just want to impress you. So engage some serious active listening: nod, smile, look inquisitive. And an addendum to the above: active listening isn’t literally about not saying a word. Despite its name, active listening actually means chipping in with the odd interjection, comment, or question, which demonstrate not only that you’ve heard what your date has said but that you’ve formulated it in your mind and served a portion of it back to them as a question, which then acts to further the conversation. This shows your date without a doubt that you’re sincerely there with them—present. They know that you’re valuing their time, their thoughts, their words.

2. Body language

You don’t need a PhD in Psychology to keep an eye on some basic physical cues to how the conversation’s going. For example, if your date is fidgeting, they’re either nervous or—worse—they’re bored. And the same goes for you—be mindful of how you’re presenting physically, because your date is likely reading your cues as well.

If they’re looking uncomfortable, perhaps the conversation’s veered into dodgier terrain. Grab the wheel and get back on solid ground. If they relax again, you’ll know why. They might also be looking awkward if you’re being a bit too forward, so keep an eye not only on what you’re saying but also how your body is oriented relative to theirs. If you’ve accidentally encroached a little on their personal space across the table, or your amorous gaze has gone full-blown obsessive stare—ease up, sit back, and let the space between you breathe. We’ve all been guilty of these faux pas—the trick is to be mindful of your physicality, and self-aware enough to pull back. This is always made more difficult when you add a glass or two of wine into the mix, so know your limits, and keep things casual.

How to answer questions

You’ve asked a potent question, and your date’s enthused as they happily tell you all about themselves, their life, their interests. You sit back, take a sip of wine, and smile. That’s the hard part over. Right?

…Probably, yes—but it does also pay to know what to keep in mind when your date reciprocates the question.

First: answer truthfully. It can be tempting to exaggerate your traits, your accomplishments, but in the long run you want to avoid doing this. If you’re serious about this person, you need them to like you for you, not some fabricated version of you which in time they’ll eventually see through. Don’t falsely advertise your lifestyle, your successes. By all means accentuate your positive characteristics, but don’t deceive. You’ll only achieve a real connection with your date if you’re authentic.

Second: avoid oversharing. If your date asks an innocuous question with an unexpectedly complicated answer, don’t go into too much detail if there’s any chance you’ll put them off. All that stuff can come later, in good time, and in the right context. Of course, don’t dismiss the question out of hand: you’ll come across as rude, weird, or secretive. Just summarise, politely allude to the fact that “It’s a long story”, and they should take the hint.

And lastly, and most importantly: modesty is everything. You might have an incredible backstory, a career that’s up in lights, and a proverbial trophy cabinet chock-a-block with prizes reaped during your star-studded life. Great—but let your date work all that out for themselves. By being humble, you demonstrate that you value empathy and personal integrity over material matters—and ultimately, that’s what will win them over.

Topics to avoid if you want to clinch that second date

If you ask something too personal, your date may feel like they’re being put on the spot. No one wants to go on a date that’s more akin to a job interview.

There’s also the famous trinity of no-go topics on a first date. You know them already—everybody does—but in case you need a reminder:

  1. religion
  2. politics
  3. exes!

These subjects can be controversial and cause avoidable and unnecessary tension at a time when you should just be enjoying getting to know one another. Furthermore, be wary of any conversation that’s overtly future-oriented—particularly about marriage and kids. You risk coming across as intense. Your date may well want those things too, but there’s a time and a place. Current affairs may also seem like a good ice breaker, but be cautious—what’s going on in the news is pretty much always linked to politics in one way or another!

Bonus round: 10 questions for an awesome conversation!

  1. “What did you want to be when you were a kid?”
  2. “What’s the single most interesting thing that’s ever happened to you?”
  3. “Do you prefer planning or being spontaneous?”
  4. “What’s the most important thing in your life?” (This one is potently open-ended. Your date can interpret it in any number of ways.)
  5. “What are you most passionate about?”
  6. “How would your friends describe you in three words?” (Ah, the good old power of three.)
  7. “Do you find it easy to open up to people?”
  8. “What’s the hardest thing you’ve ever had to do?”
  9. “What would you consider to be your greatest accomplishment?”
  10. “What do you value in a friend?”

Have fun. Flirt. Be merry (but not too merry). Above all else, make your date feel special—and you won’t go far wrong.

Oh—and if you’d like to go on a seriously incredible date but you’re just not finding singles of the calibre you’re looking for—we can help.

Drawing Down the Moon is a multi-award-winning dating agency. Our world-class matchmakers are renowned for successfully pairing intelligent, empathetic singles who are ready to meet someone equally impressive—and unbelievably compatible. Whether you’re 20 and yet to embark on your first serious relationship or 85 and ready to fall in love once again, Drawing Down the Moon has a thriving network of singles excited to meet you. Get in touch today to start your journey. We’re here to make it happen.


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Written by : Drawing Down the Moon
- Posted in: Conversation, Dating Tips, Meeting New People, Tips for Men
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