Guy's Behavior

What does this mean? What is he doing or trying to achieve?

My best friend has an older brother, like a year older than me and she (best friend) is a year younger than me.
She turned 18 this year and it's legal drinking age here. We had a bit to drink, I was drunk but I remember most of the night. Her brother who I'm also kinda friendly with was sitting on the couch with me and a couple of other people while my best friend was telling a story. I was kinda swaying while I sat and he held me still for a couple of seconds before gentler rubbing his fingers lightly across the middle of my back, until I got up to talk to people. (So like for 5-10 minutes)
I'll admit, I liked it, it was comforting or something I don't know but does it mean anything?

He often just messages me out of the blue and the last two or three times he was asking my plans for the future etc, I asked the same questions back to not to be dry with the conversation. He keeps mentioning wanting a girlfriend.

So yeah I guess my question is what's he doing?

What does this mean? What is he doing or trying to achieve?
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