Logan Stiles

Logan Stiles was a roommate of Ashlyn Shelley in 2006. He worked as a fireman for the Cambridge F.D. He is described as tall, with dark hair and chiseled features, with the look and build of a guy who works out all the time. Jake admits to being jealous of Logan for being everything he was not, as a man, also admitting that he wouldn't have had to be turned into a woman to acknowledge that he was attractive. He is said to have gone through girlfriends "like most people go through those little bags of potato chips."

Logan and Ashlyn had a playful, flirtatious relationship, and he felt no hesitation to tickle Ashlyn at will, then kiss the top of her head. When Jake, as Ashlyn, decided to start working out, Logan offered her the use of the weight room at the fire station, where he spotted, encouraged, and offered advice to her. Watching him work out, she noted how "good-looking" he was, causing some embarrassment and confusion.

It was through working out with Logan that Jake, now permanently identifying as Ashlyn, met Matt Anderson, a fellow firefighter. After the two became serious, Logan seemed to find more reasons to avoid Ashlyn, which she theorized as being because of a crush.