As the 88th annual Academy Awards loom, so too have the questions surrounding Leonardo DiCaprio and his dogged pursuit of the gold statuette. Will he finally take home an Oscar? Will he and Kate Winslet pull a repeat of last month's SAG Awards and snatch our edges once again with their mesmeric perfection? If Leo wins, will he be overcome with emotion and deviate from his pattern of political speeches, or will he carry on reservedly as if he — and cinephiles the world over — haven’t waited with bated breath for this very moment?

Considering Leo's longtime friendship with Kate Winslet, we’d hope the Academy Award-winning star would touch base with the Oscar hopeful before the ceremony and perhaps share some tips for his acceptance speech, should he win. In fact, we even imagined what that conversation might look like.

Check it out.