Okay I’ve got it. Jason Momoa is a soulful artist turned boat mechanic after his baby sister Auli'i Cravalho was placed in his care. At sixteen, her goals include winning the upcoming inter-school gymnastics competition, getting an A in maths, and finding love for her stupid big brother. She keeps setting him up with tourists coming to Hawai'i - Uzo Aduba, Oscar Isaac, Andy Samberg (they have a hilarious bro date), Angel Coulby, etc.
But then! His childhood best friend, John Cho, has returned to the island after years away, and all of Jason’s old quiet pining returns. Auli'i realises this, and shenanigans ensue involving all the previous dates and basically half the island.