The Secret to Moving on to a Second Date

Oct 22, 2023

Do you find yourself bored to death on first dates?

Or maybe it’s not quite that bad, but the conversation isn’t exactly setting the place on fire, and frankly, neither of you are particularly inspired to repeat the performance?

It may well be that you need to learn to “really listen” on that first date and be genuinely interested in finding out more about the person you’re with.

Chances are you can already relate to how important it is for men to actually listen and care about what’s important to you. So many guys just fire on all cylinders about themselves without asking you a single question.

But it goes the other way too of course. We women can be guilty of the same, and especially if we’ve decided right away that a guy we’ve just met isn’t especially interesting or attractive, we often shut down and don’t make an effort to find out more. I think this could be a mistake.

Many of the women I work with say that they’re fed up with dating and ending up in boring conversations – but guys feel like this too, and often they won’t be showing their best, most enthusiastic side when you first meet them. Or they’re a bit nervous – this is especially likely with “nice” guys – and so they might not make a great first impression.

The best thing you can do here? (no, don’t make your escape out the back door…)

Approach with curiosity!

If you do your best to find out what your date cares about and why, find out what really floats his boat, and properly listen to what he’s saying. This can open up an exciting conversation you perhaps weren’t expecting!

A “spark” is something created by two people making a connection. You can jump start things by coming to your date with fun energy and showing genuine interest. If your date is worth his salt, this will have him matching your enthusiasm and you have a chance of making something good happen.

So this means ditching the small talk. It’s really worth coming to your date with some interesting questions.

So instead of asking:
“What do you do for work?”

You could ask,
“If you could have any job in the world, what would it be, and why?”

You’ll find out lots more interesting stuff that way. Scroll down to the bottom of this post and you’ll find a list of potential first date questions to get the conversation going in a deeper direction. You could even tell your date that you’re coming with questions and maybe he’ll want to bring some of his own. You can have a good laugh with it then and likely get some amazing conversations going. And you definitely won’t run out of things to talk about.

Another important point to bear in mind is that listening is far more important than talking when it comes to being attractive on a date. That’s supported by research findings.
To be good at conversation you don’t have to be great at telling jokes or be a fabulous raconteur, and you don’t have to have had amazing experiences you can wow people with.


The important thing, and the trait that has people wanting to come back for more, is having that curiosity and a genuine interest in finding out what makes the other person tick – and listening.

Now, I can imagine you thinking right now,
“That’s great – I can approach with curiosity, but the bigger problem is that most guys want to talk about themselves for the entire date!”

Yep, this is a common issue, and if you’re in the very early stages of getting to know someone it’s probably best dealt with in a warm, accommodating, maybe a fun way. He might just be trying to impress you and it doesn’t occur to him that he’s supposed to be taking turns. Best not to shut the whole conversation down though without giving him a chance.

Maybe say something like:
“Wow – I think I’ve got enough now to write your autobiography, how about you ask me a question now!” (said with a cheeky smile)

Or you could sit back and go silent for a little bit. You’re not 100% responsible for keeping the conversation going.

Hopefully he’ll get the hint. And of course, if you have your questions to take turns and have a bit of fun with, then you won’t have this problem in the first place.

So here’s your challenge, should you wish to accept it:

On your next first date, whether you fancy the guy or not, do your best to be curious, to ask deeper, more interesting questions, and to properly listen to the answers.

At the very least you’ll have a fascinating conversation, but of course it may turn into a whole lot more. You’ll stand a much better chance of making a meaningful connection, and of actually having fun.

And that will have you both wanting to come back for more ;)


And here is a list of potential questions you could take with you to a first date (I’m sure you can think up lots more):

1. How would you like to change the world?

2. What’s your most embarrassing memory?

3. When you were young, what did you want to be or do when you grew up? Did this happen?

4. If you could time-travel and give your 14-year-old self a piece of advice, what would it be?

5. If you could invite any celebrity or historical figure to dinner, who would it be and why?

6. What’s something you’re looking forward to in the future?

7. What’s something that you’ve always wanted to try, but haven’t yet?

8. What are you most proud of yourself for?

9. Do you have a place that’s special to you? Why’s it special?

10. What would be a perfect day for you?

I’d love to hear how you get on with these – do email and tell me! x

Mairi Macleod PhD