haven't seen anything that helps with making anna at ease with sharing you yet and I'm stuck on it.

go to the bar, encounter the Hawaiian girl . Have sex with her and get caught. then go to the beach over and over until the blonde gir tries to flirt with anna. then take her back to the room, then its barbecue chicken from there

Best order seems to be:

-Go to the Bar and agree to have sex with Leilani. I'm not sure if dialogue choices matter but I told Anna that she did ruin the vacation when she catches you.

-On the next trip, keep reloading your save on Friday when visiting the Beach until you get the event where Anna forgets her sunscreen. This is where you'll meet Freya.

-Do the same thing the following week until you get the follow-up event where Freya attempts to hit on Anna.

what if leilani doesnt appear at the bar at all