9 Questions You Should Always Ask On A First Date

It’s common to worry about what you should say on a first date.

You’re always trying to strike that balance between being curious while still having fun. This isn’t tough to do – but knowing the right questions to ask on a first date is the key to discovering the mind of the guy in front of you.

couple holding hands on the street

Now, I don’t recommend using these as “interview” questions, as if you’re a chat show host trying to get a juicy story.

Instead, sprinkle a handful of these 9 questions on your next first date. Let the conversation flow naturally, but don’t be shy when it comes to actually finding out more about him.

You’ll soon know whether this guy is someone you want to see again…

1. “What do you do for fun?”

couple laughing while taking a selfie

Yes, it’s obvious. But it’s also important to learn how a man spends his free time.

If you like being super-active and running 5 miles on a Sunday morning, you may not be compatible with a guy who spends Saturday nights getting paralytic drunk and clubbing until 4am.

Sure, you don’t have to share every interest, but you should be looking for compatible lifestyles.

And if he can’t really think of answer to what he likes doing, that in itself tells you a lot about his level of passion for life!

2. “Why do you love (x)”? 

It’s one thing to hear a guy loves his job or passion, but you’ll also learn a lot by asking why he loves it.

This enables you to understand what gets him truly excited in life. Is it achievement? Making money to fund an expensive lifestyle? Or is it pursuing a skill or artistic vision?

Learn what drives a man and you’ll understand him on as deeper level than anyone else. Plus, it will tell you whether you share similar values – a crucial test for long-term compatibility in a relationship.

3. “When was your last relationship?”

couple talking at the table

This might seem a little too personal as far as first date questions go, but it’s actually crucial to know.

If he says he’s never had a real relationship and he’s over 30, that could be a crucial warning sign that this guy has commitment problems. Or, if he’s barely been out of his last relationship for a month, chances are he’s not emotionally over his ex yet.

I’m not encouraging you to be judgmental here, but just note his answer: it may be tell you where this guy is at in his life right now and what he’s looking for.

You can also follow this up by asking “How did your last relationship end?”, but only do this if you can ask in a very relaxed, curious way so that it doesn’t come off as intrusive – this is also a great question to see if he’s emotionally ready for a relationship at the moment.

4. “How would people close to you describe you?”

Sure, you could just ask him to describe himself. But you get a much more honest picture if you ask a guy how others in his life think of him.

It forces him to dig deeper and think back to comments he’s had from friends and family about his personality. E.g. “People say I’m introverted,” or “My friends all think I’m really spontaneous and jokey”. You’ll probably get a mix of positive and negative traits.

Either way, you’ll get some interesting intel on him when you ask this question, so it’s worth throwing it out there.

5. “Where do you see yourself in 5 years?” 

man looking at the ocean

As well as knowing a bit about his past, it also helps to find out his plans for the future.

Does he want to still travel around the world with a backpack for 2 years? Does he have a career or at least a vague plan for one that he can decide on? Does he mention the words “family”, “marriage” or “relationship” at all?

It’s obviously not important that he has ALL the answers, but guys usually will give you signals as to whether they still want five more years of rootless bachelordom or five years of building a meaningful relationship with someone they love.

6. “What matters most to you in the world?”

Just about every man spends days, weeks, months, and even years scheming about some big dream they have.

Ask him what he cares about, and you’ll get an insight into what occupies his thoughts on a daily basis.

Maybe he’s a studious Type-A overachiever who cares deeply about success, or maybe he wants to be able to take care of his parents in their old age, or perhaps he’s a free spirit and just looks for adventure and inner happiness.

You don’t really know someone until you know what they want in life – learn this, and you’ll learn if you can see your plans fitting in well with his.

7. “What do you look for in a partner?”

man thinking about a woman

As far as first date questions go, this is VERY direct. But it works.

When you ask a guy what he wants in a woman, you’ll often get surprisingly honest answers. (Pro tip: Be very non-judgmental and just listen to what he says. If he feels like you’re about to criticize his answer, he’ll close up and be less honest in his reply).

He might say anything: ambitious, nurturing, independent, funny warm, sexy, intelligent…

Give him plenty of space and you’ll find out some of the traits that matter most to him. This is golden information if you like this guy, and it lets you test out whether you’re the kind of person who would fit into what he’s looking for (and whether you want to be).

8. “Are you close with your family?”

Although asking a guy about his family may seem a little personal, you can at least get a sense on how he views these crucial relationships with the people who know him best.

Of course, if this brings up anything that’s super uncomfortable for him, like a terrible relationship with his Dad, or a sibling he can’t stand, then drop the subject.

But if he’s willing to open up about it, you may get a sense of where this guy comes from and how he deals with family in his everyday life (as well as what his vision is for building a family in the future).

9. “What was the last great book you read?” 

Ok, this one is for the smart women out there: this is one of the absolute must-ask questions to ask on a first date if you care about having a guy who matches your intellect. It doesn’t really matter what books he’s into, as long as he has an answer that isn’t, “Um…I don’t read”.

But if brains aren’t a big deal for you, then skip this last one! Your call.

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2 Responses to 9 Questions You Should Always Ask On A First Date

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  1. Carol Edic says:

    Great article. I am much older than the 20 or 30 something this article implies, but these questions would generally work for any age up to 80 and beyond. (I’m not that old yet!) And questions would work for men to ask women as well.

  2. Emily says:

    #1 and #2 are great for asking anyone getting to know (or getting to know on a deeper level). And think I’d learn something more/new about my fiance were I to ask him some of these again.

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