I'm a plat and my Fiancee is a silver (because of me). I always split the record so I get the upgrade in advance. If hers does not clear by the time we're on the plane, I would end up making someone's day by giving the person sitting next to her my seat (since she likes the window seats, I would end up trading my F seat for a middle - now that's dedication!) I always mention this to the F/A first - they're fine with it.
Of course, it has never come up - we're batting 1000 when we travel together!
I would take that route next time. It seems that the odds of you both getting up front are better when one person has already been pre-upgraded.