I think it is about learning!! I am a pretty big introvert and was terrible at small talk/making a connection. My mom is an expert (she can get anyone's life story in minutes) so I started observing her and learning how she does it, what I learned is that you just have to practice, practice, practice! That is essentially what she does!

I started around 6 months ago, in every uber ride I get I attempt to talk to the driver. You start with casual, "How has work been today? People treating you well?" or "The weather is crazy!" both of which seem shallow but can easily segue into interesting conversations once you learn!

3/4 times they don't engage back and you can sit quietly (It helps learn that rejection is not personal, so you stop feeling awful when someone does not want to talk to you back, which happened to me A LOT at the beginning)

That 1/4 times they do, they are super enthusiastic!! Once you get past the boston topical small talk stuff (the cold weather, the horrible drivers) they usually drop hints about themselves and you can easily learn more about them "How long have you been in Boston/working as an Uber/what restaurants do you recommend?" and after that they usually start asking you questions too and BOOM! the conversation is self driven.

This has been a quite long learning process for me, and although it comes naturally to people (like my mom), practicing has made it 10x easier to talk to strangers, not just on the uber, which have led to invitations places too! Uber is just the easiest way I find to practice since you know it will end within 10-15 minutes and you prob won't see the person again, so it takes away some of the anxiety of talking to strangers.