Dating Tips for Men: Ask the Right Questions on a First Date

dating tips for men

Have you ever been stuck in a rut of awkward or boring small talk on a first date? Have you felt unable to turn the conversation around and into something more deep and meaningful? Has conversation ever dried up to the point that neither of you know what to say next to break the silence?

If so, you’ll have experienced first-hand that unsuccessful dates are based on lame conversations. What you may not realize is that lame conversations typically result from dull questions being thrown back and forth like hot potatoes.

By understanding the tremendous power that the right kind of questions have in enriching conversations, you can prevent awkward exchanges on first dates forever. You’ll soon see for yourself that engaging questions bring first date conversations to life.

In this article, I’m going to share dating tips for men, focusing on a fundamental interpersonal skill – the art and science of asking captivating questions.

Dull questions vs. captivating questions

Dull questions are the kind that typically get asked on dates, often in the exact same way, every time. These are questions like:

  • What do you do for work?
  • Where do you live?
  • What are your hobbies or interests?
  • Do you have any pets?
  • What is your favourite colour?

Zzz….. Kill me now!

Although these kinds of questions can be helpful in learning a few key facts about one another, they can also make you seem unoriginal or unimaginative for asking them.

What’s worse is that if you ask questions like these in rapid succession, it often makes her think, “Oh, here we go again, another boring guy, asking the same tired old boring questions who seems completely incapable of getting to know the real me!”

Naturally you’d rather have her thinking the opposite; like, “Wow, he seems really interesting and a great listener too.”  You can use the ‘Captivating Question’ technique to make that happen. It’ll powerfully distinguish you from all the other guys who have bored her to death on past dates.

I define captivating questions as those which inspire emotion, imagination or disclosure of personal or intimate details. A few examples of these types of questions are:

  • If we could go on a trip together anywhere in the world, starting tomorrow, where would we go?
  • What’s the best gift you’ve ever given to someone?
  • What does your perfect weekend look like?

These questions are the next level up in conversational sophistication, compared to the duller, more typical date questions. They require your date to think deeply about how she feels and what she values, and then talk about it. It’s like speaking directly to her heart, instead of having her spout facts without thinking off the top of her head.

Once you start asking captivating questions on your first date, you’ll start to notice that:

  1. She thinks you’re an interesting conversationalist and thoughtful listener.
  2. You derail your conversation from heading down the typical tracks of other lame first dates.
  3. You find out something really interesting about her, so you’ll enjoy the conversation more and engage with her better.

To be clear, I’m not suggesting you completely abandon asking some of the more mundane questions on your dates – that would be very difficult and it’s not necessary either. I am however urging you to try out something that you’ll both benefit from.

Try to increase the ratio of captivating questions in your conversation and you’ll shift the conversational vibe from dull and factual to being more fun, creative and emotionally exciting. Needless to say, the latter type of conversation is far more engaging, memorable and ultimately more likely to lead to a second date.  You’ll stand out in her mind and she’ll likely stand out in yours too.

How to spice up a conversation

Always have 2 to 3 of your favourite ‘go-to’ captivating questions memorized, which are ready to drop casually into your date conversation at any time. Once you know what makes a good question, it only takes a few minutes to think of some. Captivating questions all have one or more of these qualities in common:

  • Inspire imagination. Make her imagine a situation and then describe it:

If you could do any work, other than your current job, what would you do?

If you could be famous for any one thing, what would it be?

  • Invoke strong emotions: make her feel or remember a particular emotion in order to answer your question. And it doesn’t have to be a positive emotion either; emotional highs and lows create powerful connections. The most engaging stories and conversations have an emotional rollercoaster element to them. Example emotional questions are:

What’s the best gift that you’ve ever given someone?

What’s the most embarrassing thing that’s happened to you recently?

  • Surface personal values, or intimate information. Once you’re both getting comfortable in the conversation, it’s good start boldly posing some pretty personal questions. If the vibe of your interaction and the tone of your question is right, you’ll be surprised at the extent to which she confides in you. Examples of such intimate questions are:

What were you like as a child?

When was the last time you cried?

Of course, be ready to answer any questions that she asks and openly divulge personal information and stories about yourself too. It’ll encourage her to do the same.

Start practicing now

This article isn’t intended as dating theory for you to ponder over for your intellectual amusement. Instead, you need to act on it and make a habit of asking more engaging and captivating questions in all of your dates, starting now.

To begin making this habit a reality, here are a few key pointers to get you started:

Make a list of your favourite captivating questions. Now that you know the qualities that make conversation interesting, set a timer for five minutes to think up your own captivating questions. If you need more inspiration or ideas, check out the top 10 questions in my free Captivating Questions Cheatsheet, which you can download from my bio. These questions have each been tried and tested hundreds of times, and are mine and my clients’ all-time favourite date questions.

Practice using the questions on friends and then refine them further before a date. You want to avoid your questions sounding clunky, rehearsed or contrived. The way you naturally speak is probably quite different from how you write, so please ‘road test’ your list of questions, prior to using them on a date. Say them to yourself out loud a few times, practice them on your friends, and refine the language to make sure that your questions sound like how you speak.

You don’t want your questions to seem too forced or randomly inserted into the conversation, so think about how you can transition to these questions from related conversation topics. Practice your transitions on anyone that’ll listen until they’re seamless. If you’re talking about a friend’s birthday, you can ask, “So, what’s the best gift you’ve ever given someone?”

If you accidentally ask a dull question, don’t sweat it, just follow up with an interesting one. Old habits die hard and from time to time, you’ll probably ask a dull question or two. It’ll just slip out, but don’t worry, all is not lost! You can always turn the situation around by following up with a more captivating question, based on her answer.  This’ll show that you’re a good listener too:

You: What do you do for work?

Her: I’m a Doctor.

You: Nice, what made you get into that? or What do you enjoy most about it?

Remember, on a first date, your primary mission is to stand out as being fun, engaging, and interesting. It always pays to break away from the typical, tired and tedious questions, in favour of a more engaging approach. And now, having those dating tips for men you have no excuse not to. Having learned the Captivating Questions Technique, and come up with a few of your own examples, you have every reason to put this into practice today. You owe it to yourself, the women you date, and your love life overall. Follow the guidance above, and start compiling and practicing your own favourite first date questions and increase the chances of your first date leading onto second and third dates.

Image: flickr

Rick is a new-school romantic, dating strategist and the founder of DateSchool. For over a decade he’s trained nice guys in the art and science of attracting awesome women. His approach helps men uncover their most attractive qualities, and to build their confidence and dating skills with women. You can download his FREE Captivating Question Cheatsheet.


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