Pushing Daisies - Ned & Chuck
Have there been more star-crossed lovers since Romeo & Juliet than this pair? In fact, I would argue Ned and Chuck are far more fatefully doomed than R&J since R&J were just a couple of kids who couldn't see past the familial issues leading to foolish deaths, but Ned and Chuck started their romance with and because of multiple deathly mistakes including that of Ned killing his mother, bringing her back to life meaning Chuck's father dying, and then after Chuck was killed herself, their romance truly beginning as Ned brought her back to life. This, by the way, causing the death of the nearby funeral owner, and leading to the eternal problem of Ned and Chuck never, ever being able to touch, or boom, Chuck's dead. Take that, Romeo.
True Blood - Sookie & Bill
Love always gets a little tricky when non-humans get involved, and that is the case for this darling mind-reading Louisiana waitress and 100+-year-old vampire. But yet, while most humans were terrified of vampires, Sookie was impossibly drawn to Vampire Bill, leading to a very, very steamy romance including some dirty graveyard sex, vigorous yet sexy blood-sucking, and an intense connection that at this point in the show, has only led to intense desire stunted by their different worlds and Bill's inability to be all Sookie needs, and his inability to avoid being the vampire she can't entirely love.
Gilmore Girls - Rory & Jess
I know plenty of Gilmore Girls fans are on Team Dean or Team Logan, but I felt as if those matches were far from perfect or star-crossed for Rory, but instead just good experiences, while Jess was more of a true, but never going to fit, kind of love for Rory. Rory and Jess began their romance with an undeniable attraction while Rory was still dating Dean, leading to some great drama with Rory realizing she couldn't deny the undeniable, then a sweet but rocky relationship until Jess took off from Stars Hollow with no explanation. Oh, those bad boys - you can never pin them down! And I don't believe Rory ever will, but they found some peace with each other over the years and I believe will always have a piece of each others' hearts.
Lost - Sawyer, Kate, Jack
All the Lost survivors seem doomed to never have anything work out, but most of all, the love affairs between Kate and Sawyer and also Kate and Jack seem doomed to never be in the right place at the right time - emotionally and physically! With Kate constantly torn between the two sexy survivors, all three fighting their own demons, Sawyer an eternal bad boy who could never commit, and Jack always suspicious of Kate's true feelings, could anyone's stars ever line up?
House - House & Cuddy
When it comes to star-crossed romance because of utter dysfunction, this is our winner! House and Cuddy have had a true yet often disappointing bond over the seasons, and also that chemistry and flirting that drives us mad that they just don't get together already! But then they both go and date other people, deny their feelings, make out then deny that, have school-girl stripper fantasies in case-solving dreams, or adopt an inconveniently timed baby, and we're back to square one of them pretending not to care about each other. With the show the better for having that tension and also with House's inability to be a decent human being, this romance will probably never be, as perfectly matched as these two seem.