10. Jessica Simpson & John Mayer: These two singers had so little common ground, they couldn’t even agree on whether they were an item. Jessica trumpeted their love in a tabloid cover story, only to be publicly humiliated when John refuted her account of a relationship. The oddest twist yet? They’re now rumored to be actually dating.
9. Hilary Duff & Joel Madden: Even beyond the age difference, these two always seemed like polar opposites — he a pierced, tattooed rocker, she a perky pop star. After their relationship crumbled, Joel wasted no time moving on to a woman more his speed: Nicole Richie, whom Hilary reportedlycalls a "skank."
8. Katie Holmes & Victoria Beckham: The unlikely friendship between Tom Cruise’s bride and the former Posh Spice was rumored to spring from Tom’s efforts to "convert" Victoria and soccer star hubby David Beckham to Scientology. Regardless, the super-skinny duo coordinating outfits and stepping out in "Stepford Wives"-style lockstep was downright creepy.
7. Flavor Flav and, well, anyone: The former Public Enemy hype man and "Surreal Life" star was 2006’s unlikeliest Lothario … and the contestants vying for his heart on "Flavor of Love" Season 2 were real pieces of work. The gal he dubbed "Deelishus" emerged victorious … but it was the bachelorette who lost bowel control who made a horrifically lasting impression on TV audiences.
6. Sienna Miller & Jude Law: The "Factory Girl" star breaks up with her Brit beau more often than she changes outfits. After the actor’s 2005 affair with his children’s nanny, Sienna took him back … enjoyed a couple of co-star dalliances … rejoined Jude … then broke it off again in November. Whatever. Wake us if there’s a wedding or a pregnancy.
5. Lance Armstrong & Matthew McConaughey: The so-called "bromance" between these two frequently shirtless studs was this summer’s buzz. Both on the rebound (Lance from Sheryl Crow, Matt from Penelope Cruz), the Tour de France champ and the "We Are Marshall" star made their way through countless bars and a bevy of babes … but couldn’t shake rumors they secretly had beer goggles only for each other.
4. Anna Nicole Smith & Howard K. Stern: A collective "Huh?" greeted Anna’s revelation that she and Howard, known to fans of her reality show as her longtime lawyer and whipping boy, were more than business associates. Even more suspicious: Anna did an about-face and now claims Howard, not ex-boyfriend Larry Birkhead, is the father of baby daughter Dannielynn.
3. Britney Spears& Paris Hilton: Just as Britney extricated herself from deadbeat husband Kevin Federline, she took up with another professional partyer: Paris. Briefly, the two insta-BFFs were so inseparable that rumors of a same-sex rebound fling spread. But their friendship ended as suddenly as it began, allegedly due to jealousy over a guy — though reports of exactly whom differ.
2. Pamela Anderson & Borat: Forget her whirlwind three-month marriage to Kid Rock. Pam’s most oddball partner this year was boorish Kazakhstan reporter Borat, aka comic Sacha Baron Cohen, who cast the former "Baywatch" star as his onscreen love interest. Somehow, even his clumsy efforts to stuff Pam into his "wedding sack" seemed more romantic than her bikini-clad nuptials with Kid.
1. Jennifer Aniston & Vince Vaughn: Were they really a couple, or did they just stage their breakup to promote "The Break-Up"? The private pair had never officially confirmed their relationship when they spoke out to refute split rumors this fall. But after two months apart (and their flick’s DVD release), the on- and off-screen co-stars confirmed that life had imitated art. Ah, well: ’Tis better to have loved and gotten press, than never to have loved at all.
Kitty Raymond is an entertainment writer who has a celebrity astrology blog at www.celebastroblogy.com.