Two Insurance Claims in Two Months

So I am somewhat reckless and will be filing  another insurance claim one month after a previous claim (for losing my phone the second time). I have used all the conventional methods to try and locate it (find my iPhone, Google Maps, Facebook, Calling, etc.) and no luck. Back in April I filed a claim for a lost phone and received a new one from Asurion and have not yet paid that deductible since it will appear in my June bill. My question is should I wait until that deductible is paid before I file a new claim or does this not matter. I know having 2 claims for the same thing back to back is not a good look, but any advice would be awesome.