Raise your hand if you hate small talk.
The word “hate” can’t even begin to describe how I feel about small talk. I’d rather indulge in awkward silence for a while than talk about the most unimportant things.
I’m by nature an introvert, which means I struggle meeting new people and going out with complete strangers. So, since I went out of my way and against my best instincts to go on a date with you, I’m gonna be picky when it comes to our conversation.
I don’t want to talk about the weather, sports, or entertainment. I wanna talk about you. And not about what you do for a living or what your hobbies are.
Well, okay, I wanna learn these things too, but I’m more interested in getting to know your deeper self; your desires, your fears, your dreams, your regrets.
I recently watched this guide from the School of Life, which introduced me to some great topics to discuss that make a date feel natural, effective, and most importantly, real.
For me, six topics stood out, which I hope will come in handy when you struggle to come up with a good topic to discuss on your dates.
Let’s take a look at them.
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1. What Has Made You Cry in Recent Times?
There are painful sides of life for everyone, no matter how ideal their life might seem to you.
On dates, of course, we rarely show the other person or talk about the bad aspects of our life. We’re trying to impress them and present them with the best version of ourselves: we’re beautiful, we’re smart, we’re social, we have goals and ambitions.
But what about the ugly side of our lives? What about the unpleasant encounters with our boss, the fights we have with friends, the serious disease one of our parents battles?
It would be nice if you show your date that you are mature enough to acknowledge that life isn’t always pretty and that you’re not only concerned with what goes well for them.
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2. What Was Difficult in Your Childhood?
Everything is connected with our childhood.
The kind of people we’re attracted to, our attachment style, the way we approach our relationships and so much more can be traced back to how we were treated when we were kids by our parents and/or close relatives.
By asking someone about their childhood and especially an unpleasant memory, you can get a glimpse of their adult self.
As philosopher, author, and founder of School of Life Alain de Botton puts it:
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3. What Do You Regret?
We talk so much on dates about our career and ambitions and we rarely ever share our regrets with the other person.
And yet, the things a person regrets are far more interesting to hear than the ones they’re proud of. Why? Because our mistakes are what makes us human. When someone talks to you about the mistakes they did, and the actions they regretted, you see a raw, real, authentic side of them that it would, otherwise, take a really long time for them to show you.
Plus, as Alain de Botton explains, by asking them something like this, you’ll immediately stand out from their previous dates:
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4. What Would You Want Someone to Forgive You For?
There’s no denying that nobody’s perfect. We all have our flaws and a bad side we rarely show to other people.
Every date you go out with is a potential future partner. So it’s natural that when you start getting to know them, you want to know everything there is about them; not just their strengths but their weaknesses as well.
But, how can you ask someone what are their weak spots without making them feel uncomfortable or offending them?
It’s simple: you ask them what would they want someone to forgive them for.
In the words of Alain de Botton himself:
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5. What Have Your Exes Not Understood About You?
For me, this is the most important question you could ever ask someone you’re interested in.
The truth is, not all relationships are made to last — people change, sometimes love runs out. But, what’s also true, is that many breakups could have been prevented if the two people involved had more patience and made a bigger effort to understand their partners.
We have all been raised in different environments, by different people, who taught us different values and had a different idea of what is right or wrong. That means that sometimes we can’t help but act, think, and react differently from our partners.
By asking your date what their previous partners didn’t understand about them, you immediately gain an advantage over them. You gain information that, should things turn serious between you two, could prove to be the key to make your relationship last.
. . .
6. What Would You Ideally Want to Tell Your Mother or Father?
As I mentioned above, the relationship we have with our parents can reveal a lot about us, and especially the way we behave in a romantic relationship and how we treat our partners.
For this reason, I would say it’s essential that you get to know a bit about your date’s family background and the relationship between them and their parents.
Personally, I feel like people would understand me — and the way I act and behave in relationships — a whole lot more if they knew the back history and the complicated relationship I have with my father.
. . .
Final Thoughts
The most common answer you get when you ask a person why did they break up with their partner, is something along the lines of “I felt like I didn’t know them anymore”.
And maybe their partner did indeed change and was unrecognizable. But, most of the time the problem lies in the fact that we don’t spend enough time to get to know the other person — not on a superficial level, but on a deeper, hidden one.
Of course, at the end of the day, it’s up to you to choose the topics you’re gonna talk about with a date, depending on what makes you feel comfortable and how deep are you willing to go.
Just remember Alain de Botton’s advice:
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This post was previously published on Hello, Love.
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