7 Non-Intrusive First Date Questions To Ask Men

First dates can be very nerve wrecking. You don’t know what to wear, your hair is a mess, you can’t find that particular makeup that you feel makes you look your best, and on top of that you’re running late.

Just when you thought it couldn’t get any worse, you show up to your date unprepared…mentally. You were soo focused on looking your best that you totally forgot that you were going to have to talk to this guy. The conversations were dull and the night didn’t end up as you’d planned.


Total failure.

But what if the date night didn’t have to be like this? What if the questions you asked him ultimately made you more desirable and ultimately irresistible to his every gaze? That’s where knowing what to say comes into play. You see men want a woman that knows what she’s talking about or is at least pretending to be interested in the date at hand.

If you don’t know what first date questions to ask men, then maybe now’s the time to brush up on your conversation skills. Here are the 7 most non-intrusive first date questions to ask men.

First Date Questions To Ask Men

Before we dive into everything, understand that these questions should and must be used in a very subtle manner.


The point of asking questions is to get to know, not to interrogate. Coming off as a woman who is genuinely interested in the questions she’s asking is key to getting asked on a second date.

1. “Do you ever wish you invented something really cool?”

This question is tailored to bring out the creativity in your first date. Usually a guy with an awesome sense of humor will say out random ideas or something he’s seriously been thinking of creating. Either way, this is a good sign of a guy who’s full of fun and many more good times to come.

2. “What’s your favorite childhood memory?”

Bringing up good childhood memories is an awesome way to bring up silly memories. This first date question is definitely one you want to ask to lighten the mood and to create a more relaxed environment.

3. “Have you been to any fun concerts recently?”

What’s the best way to bring up music without asking the boring first date question of “what kind of music do you listen to?” This question! You’re subtly asking if he’s been to any fun concerts, in which case he will then reveal his interest in music. This will give you a better insight as to what type of personality he has. Music usually leads to dancing, dancing leads to drinks, drinks lead to food, the topic cycle becomes endless.

4. “Does your girlfriend know you’re out on this date?”

How well can this guy hang? This is the best way to see if your first date has a quality sense of humor. You’ll want a guy who can laugh at himself and then throw a joke back at you. Laugh it out and let the snowball effect of fun times carry on throughout the rest of your date.

5. “If you had to ask me out on this first date all over again, would you do anything differently?”

Is he quick on his toes and a romantic? Ask this first date question to your man and you’ll be surprised at what he says. He’ll either be dull and make up something corny to say it’s perfect. Or he’ll point out what he could have done better, in which case you have a guy who’s willing to learn and improve. Either way he gives you a better insight as to who he is deep down.

6. “Do you have a bucket list of things you want to do before you die? If so, what are they?”

Goals and ambitions ladies, it’s what you want in a man. Rather than asking him what he wants to do with his life (which usually leads to the iffy topic of finances where no guy really likes to go, especially if he doesn’t have them in order), you can ask him about his bucket list. The topics of skydiving, hiking, surfing, deep see diving with sharks, etc are all awesome conversation pieces.

7. “If I was to ask you three things about yourself that would want to make me get to know you better, and none of them could be about your looks or what you do, what would they be?”

Make him sell himself to you. This question is strictly designed to have the guy sell himself to you. As bad as you might want him to ask you out on a second date (if you don’t just ignore this question), you want to be the one sought after. It is not your game to constantly answer his questions and to sell yourself on why he should ask you out again. Ask this question and watch as he reveals what he believes are his best qualities.

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