Still feeling a little weak after my flu.

Name: ??
Approach: Sat opposite her on the train and noticed her hair was wet. Said the weather is terrible isn't it.
What happened: Got into small chit chat. My questions weren't that big - like What do you do for work? How long have you lived in Brighton? and my I perspectives were small rather than relating a feeling and a story.
Improvement:
(1) A follow-up deepening question - what do you like or dislike about your job?
How do you find living in Brighton? They will inspire me to give more detailed I perspectives as well

Name: Yeba
Approach: She was sitting opposite me on the train. I said
Me: "I like your bag. I think its fashionable. Is it new?"
Yeba: Thanks. (Smiling) No, it is old. I got it last Christmas.
Me: I got this bag (pointing at my bag) a couple of months ago when I started commuting. I hate my commute, it is 2 hours long, so I bought myself something nice.
You look like you do a job which doesn't need a laptop, what kind of work do you do? (I noticed she didn't have a laptop with her)
Yeba: I use a desktop. I am afraid I will leave my laptop on the train. I work in marketing.
Me: (I paused .. vacuum)
Yeba: She asked "What do you do?"
Me: I work as a Product Manager in software. I come up with ideas for software, write it down and give it to the developers to build and then show it around to different people in the company. I work with a lot of marketing people, as the products they need to be marketed. What do you like or dislike about your job - how do you find your job?
Yeba: <thinking> I have never thought about this before ... sorry I honestly don't know. (About to look away towards the window and end the conversation)
Me: No worries. I love coming up with ideas. I hate my commute. I was brain storming for ideas right now (pointing to my laptop). I sometimes carry around a little notebook and write down my ideas. I am a dreamy sort of guy. (she laughs). I day dream a lot, and its nice to get a job which pays me for it.
Yeba: Thats nice
Me: (continuing ...) I also interact with a lot of people some of them are challenging. I don't like that.
Yeba: You like that did you say.
Me: No, I don't like that.
Yeba: I was going to say that would be unusual.
Me: Actually. I had a boss who loved difficult people situations. She was a bit of a pitbull. Some people are like that. How do you find the people you work with?
Yeba: They are really nice. I work in a startup. Everyone's nice, but sometimes things get a bit stressful. There is black friday coming up. (then she starts to look down at the table)
Me: (Listening/vacuuming) Yes black Friday would be difficult
Yeba: Yes we have to get aggregates from all our suppliers. (Then she looked away to the window and disconnected)

(About 1 min later her stop arrives)
Yeba: Nice to meet you. Have a nice train ride!
Me: Nice to meet you. Have a nice day. She still only gave me a short answer. I was doing 80% of the talking. Not sure how I should improve?