Dupré spent her early childhood years in Beachwood, New Jersey, a borough near the Jersey Shore. Her father, William Youmans, owned a landscaping business and also worked as a salesman of surfing accessories. When her parents divorced, Dupré moved to Wall, New Jersey with her mother, Carolyn Capalbo, and her stepfather, Mike DiPietro, an oral surgeon. There, she attended Old Mill (elementary) School and Wall High School until her sophomore year, when she moved to Kill Devil Hills, North Carolina, to live with her father. On her MySpace page, Dupré described leaving home at age 17 to escape a broken family and abuse, but her aunt, Barbara Youmans of Seaside Heights, denied that Dupré had a difficult childhood.
"She never had a bad life when she was growing up. She had the best of everything: bicycles, clothing, O'Neill surf boards. ... She was always dressed to kill and got everything she wanted."
In 2004, at the age of 19, Dupré moved to New York City in pursuit of a music career, and worked as a waitress at a dance club called Viscaya in the Chelsea district of Manhattan. She also worked at the clubs Pink Elephant and Retox. Jason Itzler, who ran a New York escort service called NY Confidential from 2003 to 2005, met Dupré while she was working as a cocktail waitress at the Hotel Gansevoort in 2004. Dupré began working for him on the side, using the alias Victoria. NY Confidential was shut down and Itzler sent to prison by Spitzer's New York State Attorney General's office in 2005. Dupré subsequently worked for NY Confidential's former CFO, who had opened Velvet Traces in Brooklyn.
Acquaintances stated that Dupre had expensive tastes, including Cartier and Louis Vuitton consumer goods and trips to Saint-Tropez, France. The sources also stated that several of her tattoos, in Latin and Arabic, were mantras to help keep her clean—including "What does not destroy me makes me stronger," "Protect your own," and "Never give up." None admitted suspecting that she was a sex worker, believing her statements that the cash for her lifestyle came from her wealthy parents. In 2006, Dupré changed her legal name from Youmans to her stepfather's name of DiPietro, stating that she regarded him as "the only father I have known." In the same year, she answered an ad by the escort agency Emperors Club VIP, and began working for the agency under the alias Kristen. By 2008, Dupré was living in a ninth-floor apartment in the Flatiron District of Manhattan. She maintains that she was concerned about her ability to pay her rent after the man she was living with left following her discovery that he had fathered two children.
On February 13, 2008, Dupré travelled by Amtrak from New York's Pennsylvania Station to Washington, D.C., for an assignation at the Mayflower Hotel with New York Governor Eliot Spitzer. The arrangements had been made by phone between Spitzer and a booker at Emperors Club VIP, and were monitored by federal investigators who had initiated a wiretap after his bank had filed a suspicious activity report regarding money transfers by Spitzer to a front company operated by the escort service.
Caught on the FBI's wiretap was Dupré's response to the booker's mention of other escorts' difficulties with Spitzer. "I don't think he's difficult," said Dupré. "I mean it's just kind of like, whatever, I'm here for a purpose. I know what my purpose is. I am not a … moron, you know what I mean."
On March 6, federal authorities arrested four individuals involved with Emperors Club VIP, charging them under federal prostitution and money laundering laws. Initial news reports and court documents did not identify the agency's clients or call girls by name, referring to Spitzer as "Client 9" and to Dupré as "Kristen".
On March 10, The New York Times identified Spitzer as "Client 9." Two days later on March 12, the Times identified Dupré as "Kristen." Her mother, Carolyn Capalbo, told the newspaper that her daughter "was a young kid with typical teenage rebellion issues, but we are extremely close now.” Capalbo said she was "shell-shocked" when her daughter called to tell her she had been working as a prostitute.
Dupré's only public comment on the affair remained the brief interview with The New York Times which broke the story of "Kristen's" identity on March 12, in an article accompanied by photographs taken from Dupré's MySpace page. "I just don't want to be thought of as a monster," Dupré told the newspaper. "This has been a very difficult time. It's complicated." On the day the story broke, she posted a message to her MySpace page that said "Yeah, I did it"; it was later changed to read, "Thank you for your support, it means a lot to me." Dupré uploaded a second song to the Amie Street online music store around 2 a.m. on March 13. On March 14, New York City radio station Z100 played one Dupré song.
The media waited in vain outside Dupré's Manhattan apartment building the day after Spitzer's resignation
While Dupré remained in seclusion in the days after her role in the scandal became public, she became the subject of increasingly intense media coverage. The Village Voice called her "the most famous hooker in America", and the New York Post published an extensive photo shoot showing Dupré in provocative poses. By March 18, Dupré's profile on MySpace had received over 9 million page views. Dupré was reportedly offered US$1 million by Hustler magazine to pose nude, and received offers from Penthouse magazine and Vivid Entertainment.
It was not clear if Dupré would use her notoriety to gain modeling, interview, sit-com cameo, or reality television opportunities. According to Andy Greene, assistant editor at Rolling Stone magazine quoted in Advertising Age magazine, "If she was in the studio with a producer, her voice is not that much worse than Britney Spears'. ... It's not inconceivable that she could have a song as good as the stuff on the charts. ... It's a really tough road for her to have a music career because she's a prostitute. ... She had sex with Gov. Spitzer, and that's fascinating to a lot of people. But people ultimately want to read her book or see her interviewed by Oprah or Barbara Walters. They don't want to listen to her third or fourth song."
On March 19, the soft porn website Girls Gone Wild featured teasers of Dupré, shot in Miami Beach, Florida in 2003 before she had turned 18. Dupré presented the company the drivers license of a New Jersey woman named Amber Arpaio, claiming it was Dupré's own. Company founder Joe Francis—who served a year in jail for a conviction of child abuse and prostitution involving filming two underaged girls in Panama City, Florida, in 2003 who had represented themselves as adults—prepared to release a full DVD of Dupré footage from company archives. "All nude images of Ms. Dupre were taken in public places and contain no sexual contact," said Francis. "In Florida, where Ms. Dupre was filmed, the law allows even women under the age of 18 to be filmed nude with their consent."
Dupré's attorney, Don Buchwald, argued in an e-mail to Girls Gone Wild, "It was because she was underage that [Francis] sent her home on a Greyhound bus back to North Carolina. It would be outrageous at the very least to play the video of an underage female on the Internet."
On April 28, 2008, Dupré filed suit against Francis and two of his companies alleging their exploitation of Dupré's name and image, seeking US$10 million in punitive damages, but in July of that year she decided to drop the suit after Francis released footage showing her agreeing to be filmed.
In December 2009, Dupré started writing an advice column in the New York Post called "Ask Ashley".
In January 2010, Dupré appeared on the Howard Stern Show, where she discussed incidents ranged from her situation as a rape victim to how she preoccupied her mind when engaged in intercourse with men she was not attracted to.
She posed nude for the May 2010 issue of Playboy magazine.
On March 15, Dupré was given immunity by the United States Attorney for the Southern District of New York for her role in the Spitzer scandal, in order to testify at court hearings related to the Emperors Club VIP prostitution ring.
In July 2008, a woman named Amber Arpaio filed a federal lawsuit against Dupré for defamation and invasion of privacy, claiming Dupré used her lost driver's license to appear on a "Girls Gone Wild" video. Arpaio also sued "Girls Gone Wild" founder Joseph Francis.
Dupré began singing professionally when Jerry Cooper, a musician she was living with, heard her singing the Aretha Franklin version of the song "Respect" in the shower. "She had this huge voice for such a little girl", Cooper told MTV, "and so I just kind of went in and said 'Hey, come upstairs when you're done with this, and let's work on some songs'". According to Dupré, she then toured and recorded with Cooper's band, networking with people in the music industry. In 2005, she formed a company named Pasche New York, an entertainment business intended to promote her music career.
In the summer of 2006, she made an appearance in a music video for the song "Pop Off", performed by rapper Mysterious.
Shortly after The New York Times published their profile of Dupré, her single "Move Ya Body" set a record for how fast it commanded the top price on the music-download site AmieStreet.com, reaching the site's maximum of US$0.98 per download in five hours. Another single, "What We Want", was played more than 3 million times on the Internet after the scandal erupted. While some speculated that she may have earned as much as US$300,000 - US$1.4 million from download sales of her singles on Amie Street, others estimated her earnings at as low as US$13,720. Dupré's music came to be featured in mash up YouTube videos, blending her tracks with those of established artists.
Dupré reportedly is now being represented by music manager Jerry Blair, who formerly worked for Mariah Carey, but record companies seem to be waiting to make a deal until Dupré's infamous reputation lessens.
On July 7, 2008, E! reported that Dupré was engaged in talks about a proposed reality show with Handprint Entertainment, the same firm that managed the reality television careers of Nicole Richie and Pamela Anderson, and that she was considering a move from New York to Los Angeles. One of the concepts reportedly being considered was a dating program similar to A Shot at Love with Tila Tequila. Dupré will reportedly be working with the production company Reveille Productions (responsible for the TV shows The Office and The Biggest Loser) to create a reality dating show based on the theme that everyone has skeletons in their closet.
Dupré appeared on 20/20 on Friday, November 21, 2008 where she was interviewed by Diane Sawyer about her feelings about being an "escort," and the emotional effect it had upon her when the encounter with Spitzer was made public.
On July 10, 2011 VH1 premiered Famous Food, a reality series featuring seven celebrities. Ashley came in third; first and second was given a partnership stake in the Lemon Basket.