Couple Nickname: None
Dated Between: 2003

It's hard to imagine simpler times when it comes to Lindsay Lohan's life, but surprisingly, they did once exist. In the days of yore, the only drama that was surrounding Lilo was a little bit of a girlfight she got into with Hilary Duff over that era's teenage pop star heartthrob, Aaron Carter.

See, Carter was dating Hilary Duff from the time he turned 13, but then he reportedly grew "bored"—his words, not ours—and "started getting to know Lindsay Lohan." After a brief fling, though, Carter went back to Duff to give it another go, but that was short-lived as well because he ended up cheating on her with one of her best friends. Classy bro.

Despite the fact that Carter was a downright douchebag, Duff was pretty peeved at Lilo anyway, and their feud lasted much longer than either girl's relationship with Carter did: A whole nine years.