Is my boss flirting with me? Or does he just care about me?

I am really confused with whether my boss is flirting with me or just being friendly:
He winks at me
He walks past me, looks me in the eye and holds my gaze and then smiles
I passed him a recept the other day and he practically took my hand with it (Slid his hand down my hand)as he looked me in the eye and said "Thanks Skyla"
Walked past me the other day and quickly dragged his hand across my shoulder
Another co-worker who my boss has been friends with for a long time said my boss told her he cares a lot about me
Asked me to come up to his office and had a huge chat with me about random things like if I use protection, what would I do if I got pregnant, Do I do drugs? What I do in my spare time, Would I like more responsibilites with my job? Is everything alright?
Said when they sell the business one day that they are taking me with them
Always commenting me, saying I'm a bloody good worker.
When I went on holiday, he told me to be naughty but be careful.
He also said he's really excited about me turning 18 ( that's the legal drinkin age in NZ)
He walks pasts me all the time and brushes up against me.

Sooooo is he flirting?

Additional Details:


I worked with him for about 5 hours today because he was training me to be a supervisor and he didn't try touch me, or talk to me inapropriatly or make a move on me.
Even though he had a lot of chances because we were working alone together most of the time


Some people are saying if I have the same feelings for him then go on and have fun. But how would I make a move on him without hardowt showing him I'm making a move. Just in case he isn't interested in me at all and pushes me off him?