Milo Manheim is living it up on his mini vacay in Hawaii as the newest cast member of Doogie Kamealoha, M.D. for its next season. After being stood up on yet another date from an app filled with clout chasers he finds himself at a tourist bar with his best friends to try and turn the night around. However it seems like the guy can't catch a break especially when he spills the drink of a gorgeous woman at the bar. Maybe all hope isn't lost, but then again it's just one night among tourists.. Millie is suppose to be no work and all play this vacation as she finally manages to snag a couple weeks off to spend with her family in Hawaii. While she continues to deny anything between her and the guy she runs into at the bar, her mother pushes her to have some fun. But what starts out as fun and games quickly takes a turn she wasn't expecting especially since .. she wasn't being completely honest with Milo or even herself.