1 Orlando Bloom was once romantically linked with model-turned-makeup artist Jemma Kidd. The British tabloid mainstay and sister of supermodel Jodie Kidd has a number of hoity-toity types in her romantic Rolodex, including Italian construction scion Giorgio Veroni and some dude named Arthur, the Earl of Mornington.
2 Orli's longest relationship of record was with Blue Crush babe (and future Lois Lane) Kate Bosworth. The 28-year-old had been dating the Beyond the Sea beauty, six years his junior, since they met while shooting a Gap commercial three years ago. But Bloom recently pulled the plug because hectic work schedules -- Bloom filming this month's Kingdom of Heaven in Morocco and Elizabethtown in Kentucky, Bosworth filming Superman Returns in Australia -- have kept them apart too much to keep the relationship going.
3 The tabs had a field day when Bloom was spotted chatting up Christina Ricci at a recent Oscar party. Seems that wasn't all the elfen actor was up to. Ricci reportedly got a little tipsy at the soirée and Bloom held her hair back when she lost her lunch behind a local bush.
4 Bloom once had a barely worth mentioning moment of amorous intent with actress Joanne Morley, whom he met while filming The Lullaby of Clubland and dated in 1997.
5 Orlando Bloom and Keira Knightley -- what an incredibly perfect mag-cover couple they would make. Alas, while the Pirates of the Caribbean paramours are heating up the big screen (back-to-back swashbuckling sequels are in the works), they remain simply friends off screen. "I think I had a crush on her while we were filming, actually," he says. "We got on really well, but I got on really well with her boyfriend, too."
6 While Adam Goldberg has built a cult following among the indie-slacker set thanks to Dazed and Confused, the actor is best-known as Private Mellish in Saving Private Ryan and Chandler's whackjob roommate, who dated Jennifer Aniston's Rachel on Friends. And he's had a string of B- and C-list relationships: American Pie's Natasha Lyonne, Before Sunset's Julie Delpy and current gal-pal Christina Ricci. No word on whether Goldberg has ever held anybody's hair back for any reason.
7 French beauty Julie Delpy is not the reason for the breakup of Ethan Hawke's and Uma Thurman's marriage, although no one would be surprised given the onscreen chemistry Delpy and Hawke shared in last year's Before Sunset. And the two have been linked romantically since. The Oscar co-nominees were recently spotted enjoying a cosy lunch together at the trendy New York City eatery Le Gamin, with Hawke's two-year-old son Roan in tow.
8 From his infamous Oscar liplock with Halle Berry to rumored romances with Nicole Kidman and actress/model Monet Mazur, Adrien Brody has managed to earn quite a reputation as a lady's man. While he'll next be seen competing with a huge hairy ape for the affections of Naomi Watts in Peter Jackson's remake of King Kong, off screen Brody has enjoyed a series of romantic dates with his Jacket co-star Keira Knightley. The two were inseparable while filming the psychological thriller in Scotland.
9 Rumors of a romance between Vince Vaughn and the estranged Mrs. Pitt, Jennifer Aniston, were splashed across tabloids recently when the two were spotted dining together at a posh Beverly Hills hotel. It turns out the two were discussing starring together in an upcoming romantic comedy, coincidentally titled The Breakup. A frequent sidekick to Jon Favreau and Ben Stiller, Vaughn was briefly linked to Ashley Judd, Chasing Amy star Joey Lauren Adams and comedienne Janeane Garofalo, whom Vaughn once called "one of the most beautiful girls I have ever known."
10 Her seven years of marriage to Brad Pitt now officially in the toilet, Jennifer Aniston seems to be making some tentative steps back onto the dating scene. In addition to Vince Vaughn, Aniston has been spending time with French actor Vincent Cassel, her co-star in the upcoming Derailed and soon-to-be-ex-hubby Pitt's co-star in Ocean's Twelve (Cassel played the gymnastic master thief and chief rival of Ocean's crew).
11 Okay, so Ashley Judd's entered the winner's circle with race car driver-hubby Dario Franchitti. But that doesn't mean we can't look back fondly at her more carefree days on the dating scene, does it? Judd had a romance with Matthew McConaughey (her co-star in A Time To Kill), Lyle Lovett (the frizzle-haired former Mr. Julia Roberts), Robert De Niro and singer Michael Bolton.
12 Rumors, rumors, rumors. Vincent Cassel has always been surrounded by rumors: that he dated his Birthday Girl co-star Nicole Kidman, that he's dating his Derailed co-star, Jennifer Aniston, now. But remember this: the handsome French actor (The Crimson Rivers, Brotherhood of the Wolf) is married to Monica freakin' Bellucci! You know - -the only good reason to watch the Matrix sequels.
13 Boy, are we bored of the Brad-and-Jen thing. Almost makes us look back fondly on the Jen-and-Ben thing, or the Ben-and-the-other-Jen thing. Almost. But if you must know, here's the latest: Since his separation from Jennifer Aniston, the tabs have played connect-the-dot between Brad Pitt and Angelina Jolie, his co-star in the upcoming Mr. and Mrs. Smith. Of course, those are the same tabs that reported that Pitt was recently spotted with 22-year-old Maxim model April Florio. Only it turns out that it was actually a Brad Pitt lookalike partying with Florio in Greece. Which means there are two people on this planet who look like Brad Pitt.
14 What's up with Uma Thurman? Seems the Kill Bill star has been keeping a low profile (at least by Hollywood's standards) since the breakup of her marriage to Ethan Hawke. Word is Hawke had an affair with some Montreal barmaid. Or maybe Thurman had an affair with director Quentin Tarantino, who seems to have a fetish for Uma's feet. Either way (or neither way), Thurman is single again. For the moment.
15 Creepy as this may sound, Michael Jackson once asked Nicole Kidman out on a date. (It's not known whether Kidman's kids, with ex Tom Cruise, were invited). Kidman, of course, refused. Jackson, who's dropped the sequined glove and sunglasses in favor of sports jackets and pajamas, has also dated Brooke Shields, Liz Taylor and a chimp named Bubbles.
16 It's almost as if nothing more needs to be said. But that hasn't stopped us in the past, so here goes: Billy Bob Thornton, those lips, her brother, those lips, Johnny Lee Miller, Timothy Hutton, Nicolas Cage, Val Kilmer, Colin Farrell, possibly Brad Pitt, definitely those lips, Billy Bob again, various and sundry undisclosed "lovers" of both sexes, those lips. If loose lips sink ships, then Angelina Jolie would be better off avoiding the high seas.