2 Heath and Heather. It had a nice ring to it, but Heather Graham and Ledger were only an item for a while in 2001. The two met in Prague where she was filming the Jack the Ripper drama From Hell and he was filming his star-making turn, A Knight's Tale. One of Hollywood's more prolific daters, Graham has been linked to Kyle MacLachlan, Elias Koteas, James Woods, Cher's son Elijah, Friends star Matthew Perry and recently ended her five-month relationship with Sweet Home Alabama's Josh Lucas.  top

3 In Hollywood, life often imitates art. In the upcoming Brokeback Mountain, Ledger and former Dawson's Creek star Michelle Williams play a married couple. In real life, the two are engaged and expecting their first child, a girl. While promoting the film during the Toronto International Film Festival, Williams revealed the child was conceived during filming. Prior to Ledger, Williams kept a low profile in Hollywood, only dating scriptwriter Donald Ward and musician Andy Herod.  top

4 Kirsten Dunst and Jake Gyllenhaal are keeping the tabloids busy. While the two split in 2004, they've been spotted smooching all over L.A. Then came reports that Dunst was flirting with Elizabethtown co-star Orlando Bloom. Dunst denies that she and Bloom are anything but friends and sources say she even called Bloom's girlfriend Kate Bosworth to tell her so. Bosworth (in Australia filming Superman Returns) reportedly was unfazed by the reports. Prior to Gyllenhaal, Dunst was linked to her Spider-Man co-star Tobey Maguire.  top

5 Geez, who hasn't Lindsay Lohan been linked to? Jake Gyllenhaal and the Mean Girls star were spotted in May enjoying a string of dates. Just the week before he was seen kissing Maria Full of Grace actress Catalina Sandino Moreno. The 19-year-old Lohan has been involved with Jared Leto, That '70s Show's Wilmer Vanderrama and pop star Aaron Carter.  top

6 For a few years now, marriage rumors have been swirling around Tobey Maguire and Jennifer Meyer, daughter of Universal Studios prez Ron Meyer. The two haven't yet tied the knot, but they certainly seem headed that way. In the past Maguire's been linked to Spider-Man co-star Kirsten Dunst, Demi Moore, Nicole Richie, Christina Aguilera and Rashida Jones, daughter of Quincy Jones.  top

7 Maybe it's the dark roles he often takes, but Josh Lucas manages to keep a remarkably low profile. You'd have thought his part as Reese Witherspoon's southern ex-boyfriend in Sweet Home Alabama would have changed all that, but Lucas still manages to fly mostly under the radar. Except for romances with Heather Graham and Frida star Salma Hayek, Lucas' dating life remains something of a mystery.  top

8 She may not be the Housewife gracing the most magazine covers, but Nicollette Sheridan has certainly had her share of the spotlight in the past. She's been married to Harry Hamlin (L.A. Law), hooked up with singer Michael Bolton and she was engaged to hunky Swedish actor Niklas Soderblom. But her most intriguing romantic entanglement was with Aussie Simon Main, who's done some prison time for his part in an ecstacy-trafficking bust in Europe (the world's biggest, at the time).  top

9 After brief alliances with power players -- Nicole Kidman dated New Zealand multi-millionaire Eric Watson, the ubiquitous Steven Bing and Italian director Fabrizio Lombardo -- the actress is back into the musical swing of things. This summer news leaked of a romance between Kidman and fellow Aussie Keith Urban. Urban's not the first musically inclined man for Kidman: the actress had a well-publicized liaison with rocker Lenny Kravitz and a reported romance with rapper Q-Tip. top

10 It's no mystery why so many guys seem to fall all over themselves, and their significant others, to get a little closer to Angelina Jolie. Before Brad Pitt, Jolie was linked to Taking Lives co-star Olivier Martinez, who was engaged to Kylie Minogue at the time. She's been married twice, so far-once to actor Johnny Lee Miller who she met on the set of Hackers when she was just 20, and more famously (and creepily) to actor Billy Bob Thornton until the pair divorced in 2002.  top

11 Fresh gossip says that Jim Carrey and goofball actress/pinup Jenny McCarthy are an item (McCarthy recently filed for divorce from director John Asher). Carrey left his first wife Melissa Womer after eight years to tie the knot with Dumb and Dumber co-star Lauren Holly in 1996, although that marriage lasted only 10 months. The actor's also been linked to January Jones, Ren�e Zellweger and Russian ballerina Anastasia Volochkova.  top

12 No doubt you're up to speed on Brad Pitt's current romance with Angelina Jolie and his fairy-tale-gone-wrong marriage to Jennifer Aniston. Way back, Pitt had a brief romance with Geena Davis and a lengthy liaison with actress Juliette Lewis. He moved on to an engagement with Se7en co-star Gwyneth Paltrow. Also part of his busy dating past are Nicole Appleton, Demi Moore, Julia Ormond and Uma Thurman.  top

13 Ren�e Zellweger is seeking an annulment of her four-month marriage with Kenny Chesney, sighting "fraud" as the reason for ending the marriage (raising more than a few eyebrows among gossip columnists). Since then, the tabs have her seeking solace with-depending on which ones you read-singer/songwriter Damien Rice and/or ex-love Jack White (currently married to Brit model Karen Elson). Zellwegger's all-over-the-place roster of former lovers also includes George Clooney and Jim Carrey.  top

14 After the suicide of her second husband, rocker Kurt Cobain, Courtney Love took a few years to hit the dating scene. But the actress/rocker eventually dated Nine Inch Nails frontman Trent Reznor, then went on to a two-year relationship with actor Ed Norton.  top

15 Since her split from Brad Pitt, Jennifer Aniston's been on a professional roll. It seems her personal life may be heating up now, too. While the tabs were busy with all sorts of romantic conjectures about the actress and The Break Up co-star Vince Vaughn, the latest reports are that Aniston was actually (and still is) seeing her other co-star, the very big, very buff Geoff Stults (the groom in Wedding Crashers).  top