The best small talk advice I’ve ever gotten may come from Scott Adams’ How to Fail at Almost Everything and Still Win Big. While still in his corporate career, Adams took a Dale Carnegie public speaking class. One of the topics was how to make conversation with someone you don’t know all that well yet.
The technique Adams shares is dead simple and plain obvious, which is probably why it’s also, in his words, “100% effective.”
All you do is introduce yourself and ask questions until you find a point of mutual interest. I’ll paraphrase the Dale Carnegie question stack as best I remember it.
It goes something like this:
1. What’s your name?
2. Where do you live?
3. Do you have a family?
4. What do you do for a living?
5. Do you have any hobbies/sports?
6. Do you have any travel plans?
This made immediate sense to me. You graze the surface with the world’s most mundane questions, and, as soon as you find a point of common connection, you double down.
This doubling down, however, is also the key to making this technique work. “Mutual interest.” This is important. If you don’t press on the topics that fascinate both of you, you’re just checking boxes on a doctor’s initial diagnosis clipboard — and you’ll blow through that list pretty fast with these basic questions. So once you find an exit to a higher level of conversation, take it. Immediately. Don’t get stuck in mundanity town.
If, for some reason, you find these questions too personal for someone you just met, consider what Adams had to wrap his head around as well:
The secret to making the list of six questions work without seeming awkward is in understanding that the person you meet will feel every bit as awkward as you.
Adams says everyone wants to talk about interesting things and “sound knowledgeable.” If you can make that easy for them, that’s great — and what topic do we know more about than ourselves? The gist of it is this:
When you ask a stranger a personal question, you make that person happy.
It’s not awkward. It’s not disrespectful. It’s the opposite. It’s the best thing you can do.
First-Date Questions
On a first date, the pressure to converse well is amplified 100x. If the guy at the trade show doesn’t give you his card, that’s a bummer. If she doesn’t call you back after coffee, well, that actually hurts.
Emotions, desire, self-image, often, we bring much more of these to our romantic relationships than our business interactions, and it greatly increases the perceived stakes of how these interactions play out.
Learning to control our thoughts and manage our emotions is an important, long-term job. In the short term, however, we can ask better questions on our next first date. As in any conversation, Adams’ list is a great start, but here are some you can use to wade into more intimate waters, courtesy of my last date.
“What living thing do you take care of?”
She was from Colombia. We talked about family (question 3!), and realized that, in South America, family tends to play a bigger role in people’s lives. It’s neither uncommon nor frowned upon to live with your parents and grandparents at age 28, whereas in Europe and USA, we tend to usher kids into independence of all kinds at around 18.
She mentioned her family had a dog, and I joked about that being about as much work as having a baby. She took me up on it, asking if I had any plants. When I declined, she said, laughing, “Well, is there any living thing you take care of?”
The question threw me for a second — because I realized it wasn’t just a great joke, it was also a very deep, thoughtful question. “What living thing do you take care of?” It’s interesting, right? For some of us, it’s mostly our friends and immediate family. Others look after plants, animals, or children — be it as a teacher or parent. Me? I had a good answer after all: my readers.
This is hard to convey to someone who doesn’t have a large following, but when some 400,000 people engage with your work one way or another each month, many of those people grow on you. You think about them, even when you’re not making things for them. You answer their emails, even when you don’t know their names. And you take comfort in their being there, even if their presence isn’t physical. The exact dynamics of this relationship provide material for many further essays, but, for now, let it be enough that it’s a valid answer to a great question — one you might consider asking on your next date.
“What was the other plan?”
At some point during your date while recounting past events, your opposite will say some variation of the following: “I had other plans, but…” That’s because we all have plans, and few of them ever work.
It’s an experience we all share as humans and, right now, your signal to practice something Dave Schools calls ‘cognitive incision.’ All it takes is one simple question to cut through whatever noise or continuation of facts might follow and get to the bottom of this matter: “What was the other plan?”
In case of my date, the other plan was to move to Mexico with her ex-boyfriend. Oh! Instead, she did a one-year au pair program in Paris, they split, and she’s now applying to colleges in Germany. Oh again! See how we just left mundanity town and landed in the province of profoundness? What a great question.
If the opportunity doesn’t present itself, which, it almost certainly will, you can also bring this up in a somewhat natural way. When you talk about what your date is doing on a longer time frame, be it in their career or personal life, ask: “If you didn’t do this, what would you be doing instead?” This question acknowledges their current reality without diminishing it while offering a window to talk about their dreams, aspirations, and, yes, failed plans. Be sure to reciprocate by sharing a failed plan of yours.
“Do you take after your mother or your father?”
At the intersection of talking about our families and careers, we bumped into the following mystery: Why did I become a writer? As it turned out, we could find the answer in the same place.
I told her that I’ve loved reading for as long as I can remember, starting with being able to do it before elementary school and not ending with ordering English Harry Potter books when I was 13 to not have to wait for the German translation. Being a good conversationalist herself, she further asked why I loved reading.
“I don’t know. I guess I was just surrounded by books all my childhood. My mum reads like crazy. Our living room wall is just one big shelf of books. She’s easily read 1,000 crime novels. She’s always reading.”
“How about your dad?”
“Nope, him, not so much. I definitely take after my mother that way.”
That last sentence was as new to me as it was to her — and that’s why, “Which of your parents do you take after?” can be a great first-date question.
However, here’s a word of caution: First, get a feel for it. Try to guess if the question is appropriate. “One way or another, we’re all our parents,” my date said. It’s true, but it also applies to some of the things we’re not proud of.
For some people, assessing their relationship with their parents might lead to a negative thought spiral, which will definitely make its way into your conversation. Furthermore, some people didn’t have a happy childhood. People die. Couples split. Parents leave. Make sure you frame this question positively and ask it in the right context, but if you do, it can open wonderful doors.
“Why?”
Of course. The most interesting question of all. This is how my date unearthed the which-parent question. She simply kept asking, “Why?”
Usually, on a first date, especially early into the conversation, we stick to the facts. The high-level stuff. The stuff on Adams’ list. What? How? When? Where?
But facts aren’t nearly as interesting as thoughts, decisions, and feelings. Luckily, these lie behind each fact, so whenever you catch one, you can use it as a springboard to ask about them. All you need is one word: Why?
“I chose not to apply.”
“Why?”
“I forgot to pick her up.”
“Why?”
“I was sad for a while.”
“Why?”
Like Adams says: Everyone wants to talk about interesting things. Facts and figures are important, but, for the most part, they’re not what makes life interesting. People do — and people run on ideas, choices, emotions, and intentions. “Why?” is the single-greatest question to dig up what makes us live and feel alive. I highly recommend you ask it as much as possible.
Whether in dating, in business, or in life, communicating well is the key to great relationships. Take Adams’ list. Take my questions. Most importantly, find and come up with your own. When you do, the conversation will flow more often than not.
It may start with small questions, but it won’t be small talk at all.