What does it mean when a guy allows a girl to drink from his cup multiple times?

For three days I worked with a guy super nice. The first day he just looked at me, the second he actually started coming over to my section pretty often. I was at the warehouse and he was press room. He would come down just to chill. Once I was there by myself so he sat next to me and offered me his drink. I took a sip and gave it back to him and he drank from the same cup I just did.

We went to an after party and again he kept handing me his drink even though I always had a drink on my hand. I even joked that he was trying to get me drunk. He said I was so beautiful it made him speechless but most of all I was "pretty cool to hang around". He made a lot of eye contact the entire time but kept things super friendly.

My question is was he friendly or flirty? What does it mean when a guy allows a girl he doesn't know to drink from his cup?
What does it mean when a guy allows a girl to drink from his cup multiple times?
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