Depends on the guy, the context and his personality! When my crush texted me that, he was definitely flirting, but I had a feeling he liked me and I found out he did when he asked me out much later. Anyway I would like to caution you because there are a lot of players out there lately! He could just be acting weird or random too.
Not really. It depends on what he texted you. It could be a friendly wink? If he said something romantic and added a wink then yes probably, but if it was a joke or something then No. Also it depends on the person. If hes flirty or sweet or whatever.. hope I helped :)