If you never know what to talk about, keep some of these on hand

Curating small-talk ideas to keep things interesting

One of my goals this year is to speak with 100 new people, and even though I’ve grown more confident lately, it’s still a tough ask! Recently, I've been collecting questions to use in conversation with new people or people I want to get to know better, and seeing a similar post the other day motivated me to share my own collection in the hopes that they can be useful to someone else.

Since I use the flashcard program Anki every day for language study, I also have a deck of ideas and thoughts I want to review, and I throw my small talk questions in there so they're embedded in my brain when the time comes to use one (hopefully). I've also created some phone screen sized images that can be saved to your camera roll to quickly check before or during an event, or even set as your phone background for surreptitious checking.

For livening up small talk:

These questions are somewhat lighter and can probably be thrown into a conversation with a new person when you've covered the opposite and need a new topic to keep going. They focus on positive emotions, so they're good for encouraging a person to naturally bring up their own interests and exciting happenings, which is a great jumping off point for exercising your curiosity and asking follow-ups.

• What have you been excited about lately?

• What do you think is the best way to get to know you?

• What’s the last big decision you made and what made you realize it was time to do that?

• If you could take a year off to do anything, what would it be?

Fun/Hypothetical/Silly:

These questions are about things that are obviously never going to happen and can usually be answered without touching on anything too sensitive or emotional. Since they're equally (non) applicable to everyone's situation, they can work well in a group conversation without leaving people out. You can explicitly make it a game, or just throw it out there as something interesting you read recently. However, the answers to these hypotheticals can provide insight into people's interests and values, which can then be expanded on to get to a deeper place.

• What superpower would you most like to have? What's the first thing you'd do with it?

• If you could do one thing with a guarantee of no negative consequences for you, what would it be?

• If you lived 1000 years ago, what would you be doing with your life?

• If you had to choose a skill to beat 100 randomly selected people at, what are you choosing? What if it was 1,000 people?

• What if the contest was "You win if you are in the bottom 10% of people at this skill?" What would you choose to maximize your chances of winning?

More intense:

These ones are good for moving deeper and getting to the meat of what your conversation partner cares about, but perhaps carry the risk of feeling a little too intense or job interview-like depending on the situation. In particular, I think it's important to be curious and attuned to the response and ask follow-ups that show that attunement and empathy to avoid coming across like an interviewer or artificial. Try to signal empathy and interest with your body language as well (mirroring is useful here), and look for similarities to your own experiences that you can point out to avoid too much of a one-sided interview vibe.

• What’s a problem you really care about? How do you think people can work on it?

• How, historically, have you become close to people?

• What in life do you get truly excited about?

• What’s the biggest thing in your life that you kind of fell into? Would you have done the same knowing what you know now?

• What do you value in friendships? What are the best ways they add to your life?

• What traits do you envy/value in those around you?

• How would other people describe you? How does this compare to how you want to be perceived?

Here are the ‘cheatsheets’ for saving to your phone! I'm still looking for more examples, so please share your ideas in the comments, particularly if you have examples of how they've worked for you!

And here’s the post that inspired me to share this, with more question ideas that I didn’t duplicate here (though they’ve entered my own collection):

Issue #27: How to start a great conversation no matter whom you're with