He met Elaine through Ruwan, and since their job required them to interact a lot, they became quick friends. It took him a long time to realize that he had feelings for her and not until a near-death experience he gathered enough courage to confess. Eventually, Skye happily welcomes Elaine and her son Milo, as they share a home.

Milo is Elaine's son, and there's no denying it. Not only is he tall for his age he's just as brave and stubborn as his mom. Skye enjoys spending time with him since he reminds him of Ruwan when he was that age, except Milo is better behaved and considerate. Skye used to call him Little Watson until the day Milo was lost in the wilds for a whole day. Once found Skye was so proud he used the survival skills he had been taught, that he graduated to Chief Watson. Skye's biggest concern is being a good role model for Milo and that he grows to be confident in his abilities.

He's like family. Since Mateo and Ruwan were close friends, Mateo was a part of his household while growing up in Unova. Skye treated Mateo like another brother, and still to this day that relationship continues.

Levi works as a detective at the Oranberry Police Department alongside Skye. Skye looks up to him as an experienced individual on the field and the go to person with questions about the job. Over time Skye grows confident enough around him to be vulnerable and ask him for personal advice.