Sounds like a good opportunity to make a friend.
I found this handy image in some other thread.
You can get to #5 in two or three proper conversations. I've found that the easiest way to take a conversation to a more personal place is to bring up one of my own fears or insecurities. Like, I was surprised to find out how many other people have some degree of social anxiety, and how willing they were to talk about their problems when the subject came up. You'd never know it just by looking at them, and I'm fairly sure my own issues aren't obvious to other people either.
This is the general way I go about getting to know new people. Roughly in order:
- Compliment the person, remark on something they're doing, or ask a question about it. Use their response to start a conversation. "That picture's amazing. How long have you been into art?"
- Talk about something I did recently, and/or ask them about something they've done. Usually this leads to decent conversation all by itself.
- Discuss my and their interests, especially any interests we share.
- Mention something I saw or heard. "Did you hear that Alan Rickman passed away? He was the same age as David Bowie."
- Discuss preferences and opinions about entertainment. "Have you seen Breaking Bad? Did you root for Walt? When did you stop, or were you with him all the way?"
- Discuss a recent frustrating or embarrassing experience, or a general insecurity, or some upcoming event that you're nervous about. "My boss is a complete jerk. Have you ever been expected to know things you weren't trained for?"
- Discuss hot public figures. (Optional, but fun.) "Have you seen that show The Shannara Chronicles? I'm kind of into the blond dude."
- Invite the person to a casual social thing that'll give us a chance to talk more.
Most of the time, it works every time!
Just remember that most people aren't as together as they look, Many of the things that make you feel insecure won't even be noticed by others, because your mind magnifies your insecurities, and everyone has their own things to think about. If you make a genuine effort to get to know someone, they'll probably to appreciate your interest in them and be open to more conversation. Boldness tends to pay off. A lot of people just need the right thing to respond to, and they'll open right up.
I was going to say that first train must feel nothing!