I'm not sure if maybe I messed up a step somewhere. I keep trying to kiss Holly with Lena but Lola jumps in the way or Lena says no to it.Hope my guide works. It's a bit outdated in that now the actual throuple is implemented.
Also for the second option you can have Ian dating Lena before Holly. Just don't cuddle with her. So Ian sees their relationship as casual and can jump ship to Holly.