Ask questions – in a non-invasive way. Most people like to talk about themselves, and it’s nice to feel seen.

Then say the thing you want to say – because so many people forget to! Try: “Stop by again! I’d love to continue the conversation.” Or, “Here – take my number. If you ever want company at this coffee shop, I love it here and am looking for any excuse to come.” Or … “This grocery store has free cheese tastings on Tuesdays; swing by if you want to join me for cheese.” 

I’m inventing scenarios here, but you get the point. My assumption is that most people do assume a friendly interaction is a one-time thing. You’ll have to explain that it could be more … while maintaining boundaries and giving someone the option to walk away if they want to.

Also consider that these excellent social skills you’ve developed might be effective in the world of app dating. You could meet people online, set up outings, and converse like a pro. Getting to that point might be easier on apps because that’s why people are on them (for the most part).

I love an organic meet-cute, but they don’t lead to better relationships. People have been trained to look for love on their phones. You might as well start some conversations there.

– Meredith