First up on the hometown dates is Gia in New York City, where he gives him a boat tour of the city skyline. She relates that she's bad luck with boyfriends: One cheated with all her friends, the other got into awful fights. Her family is extra protective, given her past heartbreaks. Gia's brother tells her that Jake "seems okay" but advises her to "watch out." "I just want it to work so bad," Gia says.