A long time ago, I wrote an article explaining how to be interesting. Since then, I’ve been meaning to write one or more follow-up articles. (A list of articles that are similar in spirit can be found here.)
Most importantly, I wanted to write about how one of the keys to be interesting is being interested .
One of the best ways of showing that you’re interested in someone is by asking great questions.
Over the years, I’ve collected questions that I’ve thought are interesting. I’ve kept them in a list on my phone titled “Conversational Gambits”.
One day I across Glide. It’s a website/service that makes it criminally easy to create “apps”. It occurred to me that I could use Glide to make an “app” that could access a Google Sheet spreadsheet with a bunch of these questions, randomly select a question, and present it on the screen. If you swipe on the question, it will randomly come up with another. And another. A couple of screenshots are below.


You can access it here.
It opens in a browser, but if you save the page to one of the home screens of your phone, it will then open as if it’s a native app.
Let me know what you think! Is it worth spending more time on? Are there any questions that you think are particularly good for eliciting conversation and encouraging deeper conversations?
_A couple of caveats: some of the questions are a little risqué, and I haven ‘t been keeping track of where I got the questions from. In a lot of cases, I came up with them on my own. However, there are some that I stumbled upon over the years that I should attribute to others. This is the reason I haven’t been super public about the app – if a lot of people ever started using it, I would give this a lot more attention. (If it includes a question that should be attributed to you or someone else, please let me know and I’ll remove it or provide the appropriate attribution.) _