After her parents, William Youmans and Carolyn Capalbo, broke up, Ashley "used to cry about that and say how much she missed him," childhood friend Erica Kane tells PEOPLE. Adding to the heartache was her older brother Kyle, 26, who was incarcerated after a 2000 drug arrest, according to the Asbury Park Press. (More recently, on Monday, Kyle pleaded guilty to heroin charges and is expected to be sentenced to probation on April 14, according the newspaper.)
But after her mother married oral surgeon Michael DiPietro, Ashley, who was in elementary school at the time, would say even more so "how much she missed her dad. She always used to talk about that," says Kane. "[Her life] looked perfect. She was a beautiful girl, boys thought she was pretty and she got along with everybody. But she wanted her real family. She wanted her real father and her mother together and her brother back in the house. She wanted everybody under the same roof."
A Comfortable LifestyleStill, friends say Ashley had a comfortable life with her stepfamily, in a spacious house in tony Wall Township, N.J. A popular student, former classmates recall that Ashley was driven to school in a Jaguar, that she dressed well and made friends on the cheerleading squad.
"Ashley was a good girl. She was a sweetheart, everyone loved her," says a childhood pal. "She had a good heart." And a good voice. Bringing friends to her house to play with the karaoke machine in her room, Ashley would belt out songs by Brandy, the source says. Adds Kane: "She made up this whole dance to Madonna's 'Express Yourself.' We used to hang out in her play room at her house and just dance around to that song."
Moving to North CarolinaBut once in high school, something changed. In her sophomore year, she abruptly left home to move in with her dad and his new wife, attending Manteo High School in the Outer Banks in North Carolina. "It was my decision," Ashley wrote on her MySpace page. "And I've never looked back."
"She was a normal cool girl," says former boyfriend Wayne Hunter, who dated Ashley until 2003. "She wasn't a saint, but I would put her better than a lot of girls that I've known. [The recent scandal] has surprised me because she wasn't really like that."
While Ashley was popular with the boys, she had trouble making female friends while there. "She was the hottest girl in town when she was here and all the other girls gave her hell," says Hunter. "They were jealous. The girls wouldn't hang out with her. It was ridiculous. The girls here were really mean to her."
Big City DreamsWith hopes of a career in the music industry, Ashley moved to New York City after high school. "She told me she got a nice little apartment and was just starting out slow, trying to make her way up in whatever she could do," says Hunter.
Ashley took jobs as a cocktail waitress at hot spots like Retox and Pink Elephant to pay the bills while she recorded songs like "Move Ya Body" and "What We Want" in her free time, and booked gigs performing at clubs like China Club and Remote Lounge.
The aspiring singer became embroiled in the nightlife scene. "She'd roll around with an elite, older, upper echelon of men in Manhattan society, all the 'players' in nightlife and entertainment," says a source. "She would go out of town now and then but said she was working on music projects."
Unexpected FameNow that her alleged involvement with Emperors Club V.I.P. has been exposed, "she's just trying to work through it," says high school friend Joe Pawlak, who remains in touch with Ashley. "We're just trying to keep her head up and keep her strong, have her look at this as a positive. People make mistakes. All you can do is try to go on, grow from the experience."
With reporting by CHAMP CLARK, DIANE HERBST, SEAN SCULLY and ALYSSA SHELASKY