what does it even mean for the implication to be true ?
Here are the four types of ‘imply’:
$P$ implies $R$
- Some complex number is real implies that every positive number is real.
for each $x, Px$ implies $Rx\qquad\leftarrow$universal implication
- Every multiple of $6$ is even.
$P$ logically implies $R$
- $\big(A\to\exists y\,By\big)\,$ logically implies $\,\exists y\big(A\to By\big).$
$Px$ logically universally implies $Rx$
- $x\not=x\:$ logically universally implies $\,Rx.$
(For examples 1 & 2, the context is mathematical analysis. Roughly speaking, a logical truth is a sentence that is true regardless of how its non-logical symbols are interpreted. )
$\qquad$ I am holding a pen $\implies$ It is raining outside.$\qquad(1)$
This implication seems to say that it will rain outside whenever I hold a pen.
No it does not: this Type 1 example is a synthetic implication (its specific context might be right now, in Ximending, Taipei), not an analytic implication or general truth that suggests a prediction or "will / will not".
me holding a pen and seeing it does not rain does not prove that the implication is always false.
Implication $(1)$ is not at all an assertion of absolute truth, merely truth in whatever the (implicitly?) pre-agreed-on context/scenario is. Bearing in mind that truth is generally relative to the context, implication $(1)$ is indeed (always) false in the particular context that you are describing, but true in some other context.
Only when a statement/implication is true in every imaginable context do we call it logically false (e.g., a contradiction). Analogously, we have logically true (e.g., tautological) statements.
In contrast, the implication
$\qquad$ "I am holding a pen and every empty-handed person is holding no object implies that I am not empty-handed"
is logically true (Type 3 above). When you're writing the following and wanting to analyse implications analytically across varying contexts, you are probably thinking of Types 2-4 above (on the other hand, vacuous truth in the context of Type 1 is really just a matter of definition):
the implication is always false
the implication to be true, for the times when I do not hold a pen
the implication would be true when I do not hold a pen
anytime I hold a pen, the consequence in the implication will be false.