DJ is there with his reply
I'd say to get around the headphones thing just look at her, smile and mime the act of taking headphones out and you'll find 95% of them do.
As for just speaking to people it could be anything, I find observational works. Things like 'what's the book like that you're reading and would you recommend it' or even more core basic 'Man I bet you have a smile that would just warm me up on this cold day' I find cheesy works for me
It's up to you though, it's free reign as its you're life and you'll figure out alot of stuff to say. I was in a situation on a train ride that was supposed to take me 45 mins and it took me 3 hours I had to speak to people and it taught me loads, luckily I just so happened to be reading the Cube by Annie Gottieb at the time so I cubed the whole carriage haha!
Hope this helps
