Raised in Illinois, Florida and California, the frequently uprooted Dattilo made her screen debut in the adventure feature "The Legend of Grizzly Adams" (1987) alongside younger sibling and fellow actor Bryan Dattilo. The following year she began TV work with a guest shot in an episode of "TV 101" (CBS). Fresh-faced and pretty, with an edge that made her appealing to both her contemporaries and older audiences, Dattilo saw her career take off in the 1990s, with a regular role as a willful student seeking to compete on the boys-only wrestling team in the short-lived NBC teen musical series "Hull High" and a co-starring turn in the compelling horror feature "Mirror, Mirror" in 1990. That same year she essayed the part of the titular abused teen in the heralded music video for Aerosmith's hit "Janie's Got a Gun". Because of this role and memorable guest appearances on such popular teen series as "Parker Lewis Can't Lose" and "Beverly Hills, 90210", the actress became a very familiar face to young audiences. Co-starring parts in the TV-movies "Child of Darkness, Child of Light" (USA Network, 1991) and "Cruel Doubt" (NBC, 1992) and appearances in the independent features "Pyrates" (1991) and "Final Judgement" (1992) followed.

Beginning to take adult roles, the actress began her improbable alliance with quickly canceled sitcoms in 1995 with CBS' "The Office". Here she played a fresh-out-of-college employee who is just getting her feet wet in the business world. Though "The Office" left the airwaves only a month after its debut, Dattilo wasn't wanting for work, and soon landed another series, 1996's "Local Heroes" (Fox). This didn't fare any better than "The Office", and while she returned to the big screen with a supporting role in "Infinity", an independent period piece with which actor Matthew Broderick marked his directorial debut, in 1997, she was onto more failed sitcoms, this time starring on the UPN series "Hitz".

1998 saw the actress in a memorable guest stint, playing a young woman thrown in a dumpster by her betrayed former friend (Natasha Gregson Wagner) on Fox's "Ally McBeal". The following year she was featured on NBC's "Friends" as the pizza delivery person Ross has a crush on, and additionally racked up credits on "JAG" (CBS), "Angel" (The WB) and "It's Like... You Know" (ABC), reclaiming a spot in the popular consciousness of TV audiences. Dattilo returned to regular series work as the endearingly neurotic Yola, the eponymous musician's manager on the Showtime series "The Chris Isaak Show", a critically acclaimed quirky comedy that promised to stick around longer than her previous series projects.