How To Beat Small Talk: Good Small-Talk Questions And How You Can Connect More Meaningfully

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This article was written by The Zillennial Zine’s summer editorial intern Jordyn Centerwall. Find her on Instagram at @jordyncenterwall. If you would like to share an article with The Zillennial, send us an email at thezillennialzine@gmail.com.

There’s nothing worse than when you feel yourself start to slip into meaningless small-talk topics. I always find that it happens when I’m craving meaningful communication. The weather, how work is, or the “what have you been up to?” chatter sometimes feels inescapable. It’s not reasonable to expect deep, meaningful conversations 100% of the time, but you can certainly try to be more mindful about the subjects you broach. Good small talk questions are one way to solve such problems. 

Plenty of authors, columnists, Substack newsletters, and Tumblr threads have already tried to tackle this topic. Dr. Jordyn Feingold even coined the term, “big talk” to suggest that the questions we choose dictate the quality of our conversations. Obscure hypotheticals, reading more articles yourself, and conversation card games have all been offered as valuable suggestions to turn small talk into big talk. Here are some questions, and other things you can do to prime yourself for better, more meaningful, and more enjoyable communication.

The Art of Answering

Shout out to Redditizens for this one. The thread r/socialskills (which has over 5 million members) features a page dedicated to small-talk questions. The best responses aren’t questions at all. One user responds that the best way to get better at small talk is to lead by example and get better at answering questions. They argue that encouraging better small talk starts with offering more than just the minimum answer.

For example, if someone asks where you’re from, it’s easy to say “I’m from x.” This often kills the conversation by placing the burden back on the asker. You could instead say, “I’m originally from x, but I went to school at y and then moved here for z.” This way, they have a lot more to go off of. The more information you offer, the greater the chance there is for some overlap in interests and shared background.

Fun(ny) Hypotheticals

@therapyjeff

12 slightly unhinged questions to ask your partner that’ll make both of you feel super awkward. 1. Imagine a situation where someone offered you money to go no contact with me for three months. What would be the minimum amount that could make you seriously consider it? 2. Hypothetically, if I confessed that I had cheated on you one time right after we defined our relationship but it never happened again, would you stay with me? 3. If a genie offered you three wishes, but there was an 5% chance I’d disappear from your life forever, would you accept those three wishes? 4. If you learned that I’d been hired to date you as a part of a social experiment where very hot people dated complete losers like you, would you be able to forgive me? 5. If you found out that our first meeting was not a chance encounter but was actually arranged by me, how would you react? 6. You have a one-time-use Time Machine and you have to use it to alter something in our relationship. What are you gonna alter? 7. If you could meet me 10 years earlier and start our relationship then, would you do it? Why or why not? 8. If the world was ending in 30 minutes and I was trapped in a room with my most recent ex would you be mad if I hooked up with them? 9. Suppose you found out that every sweet thing I ever said to you was written by your mom. How would you feel about that? 10. Suppose you had a chance to relive our relationship from the start, knowing everything you know now. Would you make the same choices? If not, what choices would be different? 11. Imagine you discovered I had the ability to turn invisible at will, but hadn’t told you until now. How would that affect your trust in me? 12. Let’s say we break up today, if you were given the opportunity to erase all your memories of me to spare you from any pain, but it would also remove all the happiness I’ve brought you. Would you do it? #therapytiktok #mentalhealth #relationshiptips #dating #couplesquestions

♬ original sound – TherapyJeff

I’m a big fan of hypothetical questions. They might not necessarily work with every crowd, but with the right one, they can lighten the mood and provide a welcome respite from typical conversation topics. Here are a few fun ones to throw out there.

  • If a vengeful deity was hungry and turned you into breakfast tomorrow, what would you be?

This one can open the discussion of breakfast foods that align with certain personalities. It could also lead to a debate over the merits of breakfast. Is it really the most important meal?

  • If you had to marry one of your ex-partners right now, who would you choose and why? 

This question is more relevant in small talk with someone you know intimately. It certainly might not apply to all people. I like that it forces reflection on relationships that didn’t pan out, and for you to weigh what worked and didn’t work in each of them. 

  • If you sold the rights to your entire life story to Netflix or some other production company, what part of it would they make into a movie? What part would you not want them to use?

This question is courtesy of a TikTok about the Agape app. I like that it forces you to look at your life through the lens of what others would find interesting or entertaining. 

These kinds of questions have even been monetized. Chuck Klosterman’s HYPERtheticals include 50 cards with questions meant to promote better conversations and small talk. 

Games to Play

@flexfactory.store

Reply to @girlbossmanifesto_ how to use conversation card games organically

♬ original sound – Conversation Starter Games

HYPERtheticals aren’t the only games that have tried to tackle stimulating conversation. Many other conversation card games have emerged over the years. This is fascinating to me because it shows that there is a desire, but also a market for good small talk questions as well as ones that break the mold of typical chit chat. 

We’re Not Really Strangers

This game feels like it kicked off a trend surrounding conversation card games in the 21st century, mostly by aestheticizing the art of conversation. By pairing merch with the game itself, WNRS makes deep convos a brand that people can rally behind. I’ll say too, the game lives up to the hype. I played with friends earlier this year, and I definitely came out of it feeling like I knew them on a deeper level. 

The game has three levels: Level 1: Perception, Level 2: Connection, and Level 3: Reflection. Players take turns drawing cards starting with level 1 and progressing to level 3. You could also make it a daily practice and pull one card a day. Or text certain cards to people you want to connect with. There are even online versions as well that can be played. 

Where Should We Begin

This conversation card game is based on the wildly popular podcast of the same name run by Belgian psychotherapist, Esther Perel. The game features both cards with prompts and a dice to direct the type of answer that you might give. The sides include directions such as “share something funny” and “share what you wouldn’t tell Mom.” 

Make your own game!

I went on a date where we eventually pulled out a deck of cards and decided to play War. The person I was with decided that every time we saw an ace, one of us would ask a question. It was such a simple thing, but it took the pressure off to have questions directed by something else. It was at this point during the date that I learned the most about them, and we found the most common ground. Sometimes the best way to take the pressure off small talk is to take the attention off of it. 

I once spent an evening playing Minesweeper with a friend, and we made up a rule that every time someone hit a bomb, they had to share a fun fact about themselves. (Eventually in college, this turned into a mini-drinking game for us). It turned a simple game into a surprisingly personal and funny experience. Classic games like Minesweeper are perfect for moments like this, and you can play a modern version here to start your own twist.

Talking to Strangers

To finish, we must take it to the place of Malcolm Gladwell. In the opening remarks of his book, Talking to Strangers, Gladwell shares a personal story about his father striking up a conversation about gardening in a hotel lobby. The stranger ended up being a celebrity. Gladwell’s father, who didn’t follow pop culture, was oblivious to his conversant’s identity. He didn’t ask who they were when people started coming up for autographs. The rest of Gladwell’s book revolves around case studies that explore miscommunication and the tendency humans have to trust strangers–sometimes to their detriment. This opening remark serves as both a spark of optimism and a warning. “Sometimes the best conversations between strangers allow the stranger to remain a stranger,” Gladwell advises. 

This isn’t meant to scare people. Warn yes, but the bigger truth present feels fitting to this article. Some of the best interactions I’ve had with strangers have come from a place of not trying to get to know them at their most basic details. The conversations where no names or occupations are exchanged. Letting strangers stay strangers can make way for good small talk questions, driven not by the groups that one self-assigns, but by common interests instead. 

The Reddit thread from the beginning of the article had another bit of wisdom that feels imperative to share. The advice was: you can’t connect with everyone. You are only in control of your half of the interaction. No matter how many good small talk questions you’ve got in your back pocket, the other person has to want to meaningfully connect in order for it to truly happen. 

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