I can tell you the truth: I am awful at small talk.

Being an introvert, the entire ice-breaking process has never been natural and is draining. I shudder to think about my first day of medical rotation. I waited in front of the door for a whole eternity, my hands wet, practicing my opening words. “Good morning, how is your health?” I don’t want to sound too general. “It is a lovely day, isn’t it?” Ugh, she is not planning a picnic; she has chest pain.

I was analyzing everything, afraid of that uncomfortable silence that occurs when there is no more small talk and you are both just… standing.

Yet here is what I have learned over the years: I am not bad at talking to people. I simply can talk about nothing. Now bring me a conversation—something that has real meat in it—and I am alive. My social skills were never the problem. The issue was that I was attempting to relate to people on a superficial level by engaging in mindless conversation when what I needed were more probing questions.

I needed to ask questions that delve deeper than the weather report.

Why Most Conversation Starters Suck?

Most of the conversation tips are rubbish.

What were your weekend activities? Comment about their shoes! Speak of current events!

These may do the trick when you are an outgoing person, but in the case of introverts such as myself, they are like acting a script in a language you hardly know. And they seldom go anywhere new. How many times have you said to someone, How was your weekend? and to be told, Good, pretty quiet, in reply? So what do you do then?

This is supported by research as well. According to Professor Nicholas Epley of the University of Chicago, more in-depth conversation is, in fact, more enjoyable and happier than small talk (source). Why then do we still go to the superficial stuff?

We are afraid. We fear expressing ourselves too intensely, too personally, or too unconventionally.

But what I would tell you is that most of the people are hungry to have more meaningful conversations. That they are as sick of traffic and weather as you are?

What Actually Works?

I have tried out dozens of conversation starters in the last few years. The majority bombed spectacularly. These five? These always make strangers, friends, and superficial acquaintances into true relationships.

1. “What’s got you excited these days?”

This is much more natural than inquiring about “highlights” or “what is lighting you up.” It is relaxed enough to be used in any context, but it allows the individuals to speak about what they are actually passionate about.

I had asked the same question to a tired-looking barista last week, hoping she would say, “Nothing much.” Rather, she glowed as she told me about a gym she had just begun. It turns out that she had been wanting to do it for months, and now she enrolled.

After spending the day in front of screens, we found ourselves engaging in a five-minute conversation about the joys of getting dirty.

The word “excited” plays a crucial role in eliciting positive thoughts, as opposed to the typical complaints of being busy or tired.

#2. “How did you get into that?”

This is my secret weapon for turning any casual mention into a real conversation. They say they are a teacher, a runner, interested in photography, learning how to play the guitar, or whatever it is; this question works.

The beauty is that it is interested without being nosy. And human beings enjoy the story of how they found something they are interested in. You get to know how they first discovered that they wanted to teach, or how they began running after a health scare, or why they took up a camera in the first place.

I was in a coffee shop with my colleague. He was about to meet his childhood friend.

They meet, and I was accompanying him. But during their conversation, my colleague’s friend talked about his recent business of beekeeping. I didn’t just think, “That’s interesting,” but asked how they got into it. It turns out that his grandfather used to be a beekeeper, and he learned to feel closer to him after his death. We talked for half an hour about family customs.

This question is effective because every person has an origin story of the things that they are passionate about, and they are hardly ever asked to tell it.

#3. “What’s something you’re trying to get better at?”

This does not sound like a therapeutic session but like normal talk. Everyone is always doing something, be it cooking, parenting, a hobby, or getting less stressed.

One of my colleagues said that she was working on saying “NO”. That resulted in an excellent discussion on boundaries, work stress, and the reason why we all feel guilty about preserving our time. It was far more engaging than the typical workplace complaints we often voice.

The term trying makes it seem informal and easy to associate with as compared to being hardcore.

#4. “Do you have any weird hobbies or interests?”

I adore these people because the term “weird” allows individuals to express the peculiar things. They tend to keep their interests to themselves.

During my most recent visit, I had a conversation with my dentist. He mentioned to me during our conversation that he enjoys collecting vintage coins.

The neighbor of mine makes small furniture. One of my colleagues is an addict of true crime podcasts and is overly knowledgeable about serial killers.

These are the things that make people interesting, and they are not likely to be brought up during ordinary small talk.

The inclusion of the word weird makes it fun rather than intrusive.

5. “What’s been keeping you busy that’s not work?”

This is a more natural way of inquiring about the life of a person beyond his or her job.

“What do you do in your leisure time?”sounds like a job interview question. This version takes into account the fact that everyone is busy and inquires about the non-work activities.

They will discuss the sport activities their children are doing, the home renovations they are undertaking, the shows they are binge-watching, or side jobs they are doing. It leaves all kinds of avenues to talk in without making it sound like you are interviewing them.

This is the thing that no one tells you about conversation starters: the question is not the only half of the equation. The other half is a genuine interest in what the person says.

According to clinical psychologist Dr. Sabrina Romanoff, meaningful conversations are all about being able to listen, validate, and connect with others (source). Even the best questions will not help you in case you are only waiting your turn to speak.

I realized this the hard way during my medical training. My mind was too busy trying to get my list of questions answered that I was not listening to what patients were saying. One old man talked about his garden, and I kept on bringing him back to his symptoms. Lastly, my attending doctor took me aside and told me, His garden is his gauge of quality of life. “Don’t hurry by it.”

That altered everything for me. I now ask follow-up questions when I ask these questions. I delve deeper. I tell something about my own experience. I make the dialogue as though I am really interested in the inner world of this individual—because I am.

I hope you enjoyed reading. This blog post comes from what I’ve learned and what I think and believe. Sign up for my Medium newsletter.

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