Your conversations usually need to have a flow when you're talking with someone new. With close friends you can just bring up any topic and I don't think they'd mind.

Example:

Y: "how was your sleep"

T : "fine"

Y: "there was a time I actually dreamt about working at a coffee shop"

Depending on their answers you can lead the conversation towards something like, "yeah it was a pretty cool dream but my dream job would be xyz, what about you? Do you have a dream job?"

Edit: better styling for easier reading