If $n\geqslant r,$ then there are such functionals (but there is unique up to constant) and they can be written down directly using any base. More precisely we can choose $\{v_1,\dots,v_r\}\cup\{v_{r+1},\dots,v_n\}$. (Compare with John's answer)
If $n< r,$ then there are no $r$ linear independent vectors, so the answer is also yes (because antecedent of implication is false)
If $\dim(E)=\infty,$ then the aswer to your question depends on wheater you assume axiom of choice (AC) or not.
If you assume AC, then the answer is yes, because we can complete $\{v_1,\dots,v_r\}$ to base $\{v_i\}_{i\in I}$ and put $\omega(v_1,\dots,v_r)=1$ and $0$ on the rest.
If you do not assume AC, then there is no way to construct such $\omega.$
Converse is always true. You prove it by assuming that $v_1,\dots,v_r$ are lineary dependen and then you plug this vectors to $\omega.$