Two Years Later: Jessica Simpson Realizes Leaving Nick Lachey Was a Mistake

When Jessica Simpson announced her split from Nick Lachey on November 23, 2005, she could have hardly imagined that two years later she'd be the one still feeling heartbroken. But while Lachey, 34, has happily moved in with his girlfriend of 18 months, Vanessa Minnillo, 27, Simpson has endured a number of high-profile failed relationships - from John Mayer to Adam Levine to Orlando Bloom to, most recently, the troubled Owen Wilson. So does all the heartache have the 27-year-old Simpson missing her Newlyweds days? "There are definitely parts of her that regret breaking up with Nick now," a Simpson friend tells Us Weekly in its new cover story. And that regret is starting to show. A source tells Us the singer spent October 26 (what would have been her fifth wedding anniversary) "looking through old photo albums that she made when she was with Nick...she said she was just being 'girlie,' but she was definitely somber." A friend explains, "Jessica thought she would be with someone right by now." But relationship expert Dr. Janice D. Bennett tells Us that Simpson, who has recently started dating Dallas Cowboys quarterback and notorious ladies' man Tony Romo (Romo briefly dated Carrie Underwood earlier this year), is often her own worst enemy. "It's possible Jessica is conflicted about being in a committed relationship again, so she is dating men who are unattainable," Bennett says. Meanwhile, during a Nov. 15 guest appearance on The View Simpson, who is currently recording a country album in an effort to revive her sagging music career, seemed to be pining for a guy not unlike the one she left two years ago: "I want a man. Somebody who's a really great family guy...Gosh, just somebody who's strong enough to be my man." For more of the inside story about Jessica Simpson's post-divorce struggles - and her new plan to find true love - pick up the new Us Weekly, on newsstands everywhere Friday! Tell Us: Did Jessica make a mistake leaving Nick?