Ashley described the romance like you would any other high school romance: "We go out to dinner, go to a movie. It's pretty boring."

Alas, like most first loves, Ashley's romance with

Ashley described the romance like you would any other high school romance: "We go out to dinner, go to a movie. It's pretty boring."

Alas, like most first loves, Ashley's romance with Matt did not last.

Following their split and a move to the east coast to begin her freshman year at NYU, Ashley began dating Scott Sartiano, a major fixture in the NYC party scene. Remember the glory days of Butter and 1 OAK? You can thank Scott. They split after one year.

Ashley then dated Tsubi jeans CEO Gregg Chait from 2005-2007, leading to brief (always rumored, never confirmed) romances with Lance Armstrong (pre-fall from grace, post-Sheryl Crow) and Jared Leto, whom she was spotted making out with at a club in 2008 (and has been spotted with several times throughout the years). Oh, those pre-camera phone days, we remember you not-so-fondly.