Love small talk with strangers, but struggle with longer-term relations as I eventually run out of things to say. How to come up with endless conversation topics on the fly?

Talking with strangers has never been an issue for me. I worked in tutoring and healthcare and got to meet new people constantly, and I actually enjoy getting to know their backgrounds. And because of that experience, I know all of the basic small talk questions and even developed a couple of stories I always tell to strangers.

But my problem is, if I meet someone for the fourth or fifth time, I run out of things to say quickly. Earlier this month I had a new co-worker at my job, and I initially had no problem speaking with him–we talked about our families, hobbies, travel experiences, dreams for the future, etc. But after the second week, I just ran out of things to talk about. We would eat lunch together and there would be awkward silences as I struggle to come up with something to say. Same problem with dating–the first date tends to go well, but after that our conversations become strained because I exhausted all of my conversation materials.

This is an issue I face even with my close friends and family. When I meet up with them, I’ll ask about anything new that’s happened and tell stories of my own recent experiences. And I’ll also talk about recent events in the news, any new shows I started, etc… But eventually, I just run out of things to talk about.

How do I endlessly come up with new conversation topics on the fly? A lot of the advice I read on the internet seems geared towards small talk rather than what to say when you’re meeting someone for the *n*th time. I was considering improv comedy classes, but also wondering if there were any social “exercises” I could practice at home to get better at this. Appreciate any advice y’all might have!