@deadrxn24,
Well, Dead, it's somewhat OT, but, for what it's worth, probably not much, and assuming my presumptions, such as they are, are valid, then
If I decide to jump, then will you first please kick me in the chest, hard as you can, in the hope of causing me to fall and break my arm, so that when I actually take the plunge, my insurance carrier will assume the fracture was not caused by a humanoid, in which case, I've been advised, I'd be ineligible
or
Stick around, Deal, if at all feasible, so if If I decide that jumping is my only alternative, then I will stand at the edge facing you, whereupon first break my arm using that handy treetrunk, then please kick me in the chest, hard as you can, in the hope of not only causing me to fall; but if I stand just above that preeminence, making it appear that the fall also breaks my arm, so that after I've actually take the plunge, my insurance carrier will assume both fractures were accidental, not caused by a humanoid, that is, in which case, I've been advised, I'd have been ineligible; whereas given both injuries as accidental, it might double; waiting, however, since I might not survive, 'til I finish this bottle of Pilsner Urquell
Ideal wording depending, of course, on exact context. Of course Dead, that is, I'm somewhat pulling your leg, I think
Most commas optional
Edited to remark re "If [he talks to her again], then [will you tell me], [so that way I have a reason to beat him up]?" I'd have omitted "that way" as somewhat redundant
Commas still optional